Heterocycle Reactions

A topical collection in Molbank (ISSN 1422-8599). This collection belongs to the section "Organic Synthesis".

Viewed by 148289

Editor


E-Mail Website
Collection Editor
Department of Pharmacy, School of Life Sciences, Pharmacy & Chemistry, Kingston University, Penrhyn Road, Kingston upon Thames KT1 2EE, UK
Interests: free radical organic and polymer chemistry; heterocyclic and medicinal chemistry
Special Issues, Collections and Topics in MDPI journals

Topical Collection Information

Dear Colleagues,

According to "Heterocyclic Chemistry" by J. A. Joule and K. Mills (Wiley, 5th Ed), "heterocyclic chemistry comprises at least half of all organic chemistry research worldwide". Many reactions proceed as predicted, while other reactions give unusual products, which perhaps do not fit the intended use but are nevertheless chemically interesting. Some reactions give more than one product, with selectivity tunable through optimization or biasing of reaction conditions. Often, interesting "side-products" are neglected in pursuit of a target compound.

This Special Issue welcomes the submission of any suitably fully characterized novel compound(s) from a given heterocyclic compound reaction. Please note that the reaction product does not necessarily have to be heterocyclic.

Prof. Dr. Fawaz Aldabbagh
Collection Editor

Manuscript Submission Information

Manuscripts should be submitted online at www.mdpi.com by registering and logging in to this website. Once you are registered, click here to go to the submission form. Manuscripts can be submitted until the deadline. All submissions that pass pre-check are peer-reviewed. Accepted papers will be published continuously in the journal (as soon as accepted) and will be listed together on the collection website. Research articles, review articles as well as short communications are invited. For planned papers, a title and short abstract (about 100 words) can be sent to the Editorial Office for announcement on this website.

Submitted manuscripts should not have been published previously, nor be under consideration for publication elsewhere (except conference proceedings papers). All manuscripts are thoroughly refereed through a single-blind peer-review process. A guide for authors and other relevant information for submission of manuscripts is available on the Instructions for Authors page. Molbank is an international peer-reviewed open access quarterly journal published by MDPI.

Please visit the Instructions for Authors page before submitting a manuscript. The Article Processing Charge (APC) for publication in this open access journal is 500 CHF (Swiss Francs). Submitted papers should be well formatted and use good English. Authors may use MDPI's English editing service prior to publication or during author revisions.

Keywords

  • Heterocyclic chemistry
  • Aromatic heterocycles
  • Non-aromatic heterocycles
  • Fused heterocycles
  • Nitrogen
  • Oxygen
  • Sulfur
  • Radical
  • Spectroscopic properties
  • Halogenation
  • Organic chemistry
  • Medicinal chemistry

Published Papers (87 papers)

2024

Jump to: 2023, 2022, 2021, 2020, 2019

6 pages, 663 KiB  
Short Note
8(S)-[(1R,2S,5R)-2-Isopropyl-5-methylcyclohexyloxy]-3,4-dihydro-2H-[1,4]dithiepino[2,3-c]furan-6(8H)-one
by Alsu M. Khabibrakhmanova, Enze S. Rabbanieva, Darya P. Gerasimova, Liliya Z. Latypova and Almira R. Kurbangalieva
Molbank 2024, 2024(2), M1820; https://doi.org/10.3390/M1820 - 11 May 2024
Viewed by 214
Abstract
The interaction of propane-1,3-dithiol with the chiral bis-thioether, which combines two 2(5H)-furanone moieties, bridged through their carbon atoms C(4) by the propane-1,3-dithiol fragment, in DMF in the presence of potassium hydroxide or cesium carbonate resulted in the formation of an [...] Read more.
The interaction of propane-1,3-dithiol with the chiral bis-thioether, which combines two 2(5H)-furanone moieties, bridged through their carbon atoms C(4) by the propane-1,3-dithiol fragment, in DMF in the presence of potassium hydroxide or cesium carbonate resulted in the formation of an optically active fused bicyclic sulfur heterocycle, possessing 1,4-dithiepine and unsaturated γ-lactone moieties. The studied reaction follows an unexpected pathway in a basic medium with the thiolate–thiolate exchange. The structure of the novel heterocycle of the 1,4-dithiepinofuranone series is characterized by single-crystal X-ray diffraction. Full article
Show Figures

Figure 1

6 pages, 1019 KiB  
Communication
Synthesis and Spectroscopic Study of New 1H-1-Alkyl-6-methyl-7-nitroso-3-phenylpyrazolo[5,1-c][1,2,4]triazoles
by Ion Burcă, Valentin Badea, Vasile-Nicolae Bercean and Francisc Péter
Molbank 2024, 2024(2), M1815; https://doi.org/10.3390/M1815 - 24 Apr 2024
Viewed by 393
Abstract
The nitrosation of 1H-1-alkyl-6-methyl-3-phenylpyrazolo[5,1-c][1,2,4]triazoles leads to new 1H-1-alkyl-6-methyl-7-nitroso-3-phenylpyrazolo[5,1-c][1,2,4] triazoles that react in acidic media, giving rise to 1H-1-alkyl-7-hydroxyimino-6-methyl-3-phenylpyrazolo[5,1-c][1,2,4]triazolium salts. These compounds were characterized by FT-IR, UV-Vis, 1H-NMR, 13C-NMR, and 15N-NMR spectroscopic techniques. Full article
Show Figures

Scheme 1

9 pages, 2545 KiB  
Communication
Synthesis and Anti-Inflammatory Activity of (Z)-4-(2-(3-Oxopiperazin-2-ylidene)acetyl)benzoic Acid
by Maksim V. Dmitriev, Ekaterina E. Khramtsova, Danila Y. Apuskin, Alexander I. Andreev, Ilya I. Kovalenko, Irina V. Mashevskaya and Andrey N. Maslivets
Molbank 2024, 2024(1), M1772; https://doi.org/10.3390/M1772 - 5 Feb 2024
Viewed by 1088
Abstract
Non-steroidal anti-inflammatory drugs (NSAIDs) are an important class of medications; however, they have some drawbacks. We are developing a new NSAID with pronounced anti-inflammatory and analgesic activities and a very low toxicity—(Z)-3-(2-oxo-2-(p-tolyl)ethylidene)piperazin-2-one (piron). In this work, we describe the synthesis of [...] Read more.
Non-steroidal anti-inflammatory drugs (NSAIDs) are an important class of medications; however, they have some drawbacks. We are developing a new NSAID with pronounced anti-inflammatory and analgesic activities and a very low toxicity—(Z)-3-(2-oxo-2-(p-tolyl)ethylidene)piperazin-2-one (piron). In this work, we describe the synthesis of the main metabolite of piron—(Z)-4-(2-(3-oxopiperazin-2-ylidene)acetyl)benzoic acid. The anti-inflammatory activity of the synthesized metabolite was determined in vivo. Full article
Show Figures

Figure 1

7 pages, 1581 KiB  
Communication
Synthesis of Substituted Pyrrole Derivatives Based on 8-Azaspiro[5.6]dodec-10-ene Scaffold
by Ildar R. Iusupov, Victor A. Tafeenko, Andrea Altieri and Alexander V. Kurkin
Molbank 2024, 2024(1), M1765; https://doi.org/10.3390/M1765 - 25 Jan 2024
Viewed by 1194
Abstract
This work describes the synthesis of spirocyclic compounds based on 8-azaspiro[5.6]dodec-10-ene. Diastereomerically pure pyrrole derivatives were prepared from the spirocyclic 1,2,3-triazole using a coupling reaction. The resulting compounds were characterized via 1H and 13C NMR spectroscopy and HRMS, and the crystallographic [...] Read more.
This work describes the synthesis of spirocyclic compounds based on 8-azaspiro[5.6]dodec-10-ene. Diastereomerically pure pyrrole derivatives were prepared from the spirocyclic 1,2,3-triazole using a coupling reaction. The resulting compounds were characterized via 1H and 13C NMR spectroscopy and HRMS, and the crystallographic characteristics of one of them were studied via X-ray diffraction. Full article
Show Figures

Figure 1

4 pages, 1252 KiB  
Short Note
3-(4-Bromophenyl)-1-carbamothioyl-5-(2-carbamothioylhydrazinyl)-4,5-dihydro-1H-pyrazole-5-carboxylic Acid
by Anastasia A. Andreeva, Maksim V. Dmitriev and Andrey N. Maslivets
Molbank 2024, 2024(1), M1757; https://doi.org/10.3390/M1757 - 2 Jan 2024
Viewed by 1381
Abstract
The reaction of 4-(4-bromophenyl)-2,4-dioxobutanoic acid with thiosemicarbazide, in a ratio of 1:2, when boiled in ethanol gives 3-(4-bromophenyl)-1-carbamothioyl-5-(2-carbamothioylhydrazinyl)-4,5-dihydro-1H-pyrazole-5-carboxylic acid with a good yield. This compound was fully characterized. Full article
Show Figures

Figure 1

2023

Jump to: 2024, 2022, 2021, 2020, 2019

4 pages, 1379 KiB  
Short Note
(Z)-1-Benzyl-5-(4-bromophenyl)-5-hydroxy-4-(2-oxomorpholin-3-ylidene)pyrrolidine-2,3-dione
by Nikita A. Tretyakov and Andrey N. Maslivets
Molbank 2023, 2023(4), M1751; https://doi.org/10.3390/M1751 - 18 Dec 2023
Viewed by 1317
Abstract
The reaction of 8-(4-bromobenzoyl)-3,4-dihydro-1H-pyrrolo[2,1-c][1,4]oxazine-1,6,7-trione with benzylamine in acetonitrile at room temperature afforded a good yield of (Z)-1-benzyl-5-(4-bromophenyl)-5-hydroxy-4-(2-oxomorpholin-3-ylidene)pyrrolidine-2,3-dione. The compound was fully characterized. Full article
Show Figures

Figure 1

7 pages, 4926 KiB  
Short Note
3-Benzoyl-2-hydroxy-3a-[(3-methylquinoxalin-2-yl)methyl]-1H-pyrrolo[2,1-c][1,4]benzothiazine-1,4(3aH)-dione
by Ekaterina A. Lystsova and Ekaterina E. Khramtsova
Molbank 2023, 2023(4), M1749; https://doi.org/10.3390/M1749 - 13 Dec 2023
Viewed by 1219
Abstract
The reaction of 3-benzoylpyrrolo[2,1-c][1,4]benzothiazine-1,2,4-trione with 2,3-dimethylquinoxaline afforded 3-benzoyl-2-hydroxy-3a-[(3-methylquinoxalin-2-yl)methyl]-1H-pyrrolo[2,1-c][1,4]benzothiazine-1,4(3aH)-dione in a moderate yield. The compound was fully characterized. Full article
Show Figures

Figure 1

9 pages, 1159 KiB  
Communication
Potassium 6-Oxo-7,13,16,22-tetraazatetracyclo[12.6.2.18,12.017,21]tricosa-1(20),8(23),9,11,14,16,18,21-octaen-2-yne-15-carboxylate
by Camille Blouet, Stéphanie Letast, Thomas Robert, Stéphane Bach, Noël Pinaud, Nicolas Joubert, Marie-Claude Viaud-Massuard, Jean Guillon, Cédric Logé and Caroline Denevault-Sabourin
Molbank 2023, 2023(4), M1735; https://doi.org/10.3390/M1735 - 9 Oct 2023
Viewed by 1197
Abstract
Potassium 6-oxo-7,13,16,22-tetraazatetracyclo[12.6.2.18,12.017,21]tricosa-1(20),8(23),9,11,14,16,18,21-octaen-2-yne-15-carboxylate was synthesized through a multi-step pathway, starting from commercially available 3-iodo-1,2-phenylenediamine. Structure characterization of this new substituted macrocyclic quinoxaline compound was achieved using 1H NMR, 13C NMR, and HRMS spectral analysis. This new macrocyclic derivative [...] Read more.
Potassium 6-oxo-7,13,16,22-tetraazatetracyclo[12.6.2.18,12.017,21]tricosa-1(20),8(23),9,11,14,16,18,21-octaen-2-yne-15-carboxylate was synthesized through a multi-step pathway, starting from commercially available 3-iodo-1,2-phenylenediamine. Structure characterization of this new substituted macrocyclic quinoxaline compound was achieved using 1H NMR, 13C NMR, and HRMS spectral analysis. This new macrocyclic derivative demonstrated submicromolar potency on both Pim-1 and Pim-2 isoforms, with an interesting selectivity profile against a selected panel of human kinases. Full article
Show Figures

Graphical abstract

4 pages, 827 KiB  
Short Note
4-(4-(2-Bromoethyl)phenoxy)-2,3,5,6-tetrafluoropyridine
by Tiffany H. Li, Lucas C. Messer, Nathan J. Weeks, Timothy J. Fuhrer and Scott T. Iacono
Molbank 2023, 2023(3), M1730; https://doi.org/10.3390/M1730 - 19 Sep 2023
Cited by 1 | Viewed by 1165
Abstract
The title compound was synthesized in near quantitative yields via initial nucleophilic aromatic substitution of pentafluoropyridine (PFP) with 4-(2-bromoethyl)phenol as a versatile precursor for ionic liquids (ILs). The purity and structure were determined using 1H, 13C, and 19F NMR and GC-EIMS. Full article
Show Figures

Scheme 1

4 pages, 612 KiB  
Short Note
4-(2,5-Dimethyl-1H-pyrrol-1-yl)-1,2,5-oxadiazol-3-amine
by Natalia V. Obruchnikova and Oleg A. Rakitin
Molbank 2023, 2023(3), M1700; https://doi.org/10.3390/M1700 - 20 Jul 2023
Viewed by 761
Abstract
1,2,5-Oxadiazol-3-amines with a heterocyclic substituent in the 4-position are being intensively investigated as compounds with valuable pharmacological activity. In this communication, the reaction of 1,2,5-oxadiazole-3,4-diamine with 2,5-hexanedione was shown to selectively give 4-(2,5-dimethyl-1H-pyrrol-1-yl)-1,2,5-oxadiazol-3-amine as a product of the Paal–Knorr reaction. The [...] Read more.
1,2,5-Oxadiazol-3-amines with a heterocyclic substituent in the 4-position are being intensively investigated as compounds with valuable pharmacological activity. In this communication, the reaction of 1,2,5-oxadiazole-3,4-diamine with 2,5-hexanedione was shown to selectively give 4-(2,5-dimethyl-1H-pyrrol-1-yl)-1,2,5-oxadiazol-3-amine as a product of the Paal–Knorr reaction. The structure of the synthesized compound was established by elemental analysis, high-resolution mass spectrometry, 1H and 13C NMR, and IR spectroscopy. Full article
Show Figures

Scheme 1

5 pages, 606 KiB  
Short Note
3-(4-(Benzyloxy)-3-methoxyphenyl)-[1,2,4]triazolo[4,3-a]pyridine
by Katrina E. Doherty, Arturo León Sandoval, Ethan T. Mercier and Nicholas E. Leadbeater
Molbank 2023, 2023(3), M1694; https://doi.org/10.3390/M1694 - 12 Jul 2023
Viewed by 880
Abstract
The [1,2,4]triazolo[4,3-a]pyridine derivative 3-(4-(benzyloxy)-3-methoxyphenyl)-[1,2,4]triazolo[4,3-a]pyridine was prepared in a 73% isolated yield by means of an oxidative ring closure of a hydrazine intermediate. Sodium hypochlorite was used as the oxidant and ethanol as a solvent, making the process a clean, [...] Read more.
The [1,2,4]triazolo[4,3-a]pyridine derivative 3-(4-(benzyloxy)-3-methoxyphenyl)-[1,2,4]triazolo[4,3-a]pyridine was prepared in a 73% isolated yield by means of an oxidative ring closure of a hydrazine intermediate. Sodium hypochlorite was used as the oxidant and ethanol as a solvent, making the process a clean, green approach. The reaction was performed at room temperature for 3 h, and then the heterocycle was isolated in an analytically pure form by extraction, followed by passing the crude product mixture through a small plug of alumina. Full article
Show Figures

Graphical abstract

8 pages, 908 KiB  
Short Note
2-Benzyl-7-(4-chlorophenyl)-3-morpholino-6-((1-phenyl-1H-1,2,3-triazol-4-yl)methyl)-6,7-dihydro-5H-pyrrolo[3,4-b]pyridin-5-one
by Perla Islas-Jácome, Cecilia García-Falcón, Sandra L. Castañón-Alonso, Ernesto Calderón-Jaimes, Daniel Canseco-González, Alejandro Islas-Jácome and Eduardo González-Zamora
Molbank 2023, 2023(3), M1693; https://doi.org/10.3390/M1693 - 10 Jul 2023
Viewed by 944
Abstract
The new polyheterocyclic compound, 2-benzyl-7-(4-chlorophenyl)-3-morpholino-6-((1-phenyl-1H-1,2,3-triazol-4-yl)methyl)-6,7-dihydro-5H-pyrrolo[3,4-b]pyridin-5-one, was synthesized by a sequential combination of 4-chlorobenzaldehyde, (1-phenyl-1H-1,2,3-triazol-4-yl)methanamine, 2-isocyano-1-morpholino-3-phenylpropan-1-one, and maleic anhydride under a microwave-assisted one-pot process [Ugi-Zhu/aza Diels-Alder cycloaddition/N-acylation/decarboxylation/dehydration] with a 28% overall yield. The synthesized [...] Read more.
The new polyheterocyclic compound, 2-benzyl-7-(4-chlorophenyl)-3-morpholino-6-((1-phenyl-1H-1,2,3-triazol-4-yl)methyl)-6,7-dihydro-5H-pyrrolo[3,4-b]pyridin-5-one, was synthesized by a sequential combination of 4-chlorobenzaldehyde, (1-phenyl-1H-1,2,3-triazol-4-yl)methanamine, 2-isocyano-1-morpholino-3-phenylpropan-1-one, and maleic anhydride under a microwave-assisted one-pot process [Ugi-Zhu/aza Diels-Alder cycloaddition/N-acylation/decarboxylation/dehydration] with a 28% overall yield. The synthesized compound was fully characterized by 1D (1H, 13C) and 2D (COSY, HSQC, and HMBC) NMR, FT-IR, and HRMS. Full article
Show Figures

Graphical abstract

7 pages, 912 KiB  
Communication
Synthesis, Characterization and Chlorination of 4-(Pentyloxy)-7-(prop-2-yn-1-yloxy)pteridin-2-amine
by Jevy V. Correia, Bruno Wilke and Carola Schulzke
Molbank 2023, 2023(3), M1692; https://doi.org/10.3390/M1692 - 8 Jul 2023
Viewed by 1161
Abstract
A new alkyne functionalized pterin derivative was synthesized through a reaction of 7-chloropterin with propargyl alcohol in the presence of sodium hydride. The purity and chemical structure of the compound was validated by NMR (1H, 13C) spectroscopy, Mass (APCI source) [...] Read more.
A new alkyne functionalized pterin derivative was synthesized through a reaction of 7-chloropterin with propargyl alcohol in the presence of sodium hydride. The purity and chemical structure of the compound was validated by NMR (1H, 13C) spectroscopy, Mass (APCI source) spectrometry, elemental analysis, and X-ray crystallography. The title compound may be further functionalized by exploiting the yne moiety, for instance, using click chemistry. The novel pterin derivative, most notably, in contrast to typical pterin behavior, is now soluble or even well soluble in almost any solvent except water. Full article
Show Figures

Figure 1

7 pages, 1985 KiB  
Communication
Synthesis, Spectroscopic, and Thermal Analyses of 2-Oxo-1,2-dihydroquinolin-8-yl 4-chlorobenzoate
by Diana Becerra, Hugo Rojas and Juan-Carlos Castillo
Molbank 2023, 2023(2), M1672; https://doi.org/10.3390/M1672 - 19 Jun 2023
Viewed by 889
Abstract
The 2-oxo-1,2-dihydroquinolin-8-yl 4-chlorobenzoate was synthesized in good yield using a triethylamine-mediated O-acylation reaction between 8-hydroxyquinolin-2(1H)-one and 4-chlorobenzoyl chloride in acetonitrile at room temperature. This methodology is notable for its clean reaction profile and straightforward procedure. The 2-oxoquinoline derivative was characterized [...] Read more.
The 2-oxo-1,2-dihydroquinolin-8-yl 4-chlorobenzoate was synthesized in good yield using a triethylamine-mediated O-acylation reaction between 8-hydroxyquinolin-2(1H)-one and 4-chlorobenzoyl chloride in acetonitrile at room temperature. This methodology is notable for its clean reaction profile and straightforward procedure. The 2-oxoquinoline derivative was characterized using spectroscopic, spectrometric, and thermal analyses, enabling a comprehensive understanding of its molecular structure and thermal properties. Full article
Show Figures

Figure 1

7 pages, 2204 KiB  
Communication
Photoinduced Ring Opening of Methyl 1-Aryl-5-oxo-6,7-dihydro-1H,5H-pyrazolo[1,2-a]pyrazole-2-carboxylates in the Presence of Diaryl Disulfides
by Nejc Petek and Uroš Grošelj
Molbank 2023, 2023(2), M1670; https://doi.org/10.3390/M1670 - 15 Jun 2023
Viewed by 862
Abstract
Among the methods used for the synthesis of functionalized heterocyclic compounds, photochemistry has gained immense popularity due to the reactivity of intermediates in photoinduced reactions. In this study, we report on the effect of diaryl disulfides as hydrogen atom transfer catalysts on the [...] Read more.
Among the methods used for the synthesis of functionalized heterocyclic compounds, photochemistry has gained immense popularity due to the reactivity of intermediates in photoinduced reactions. In this study, we report on the effect of diaryl disulfides as hydrogen atom transfer catalysts on the photoinduced transformations of pyrazolo[1,2-a]pyrazolones. After excitation with visible light, these compounds are susceptible to C–N bond cleavage, followed by intermolecular hydrogen atom abstraction. By modifying the reaction conditions, we have developed two novel methods for the synthesis of highly substituted pyrazoles. Full article
Show Figures

Scheme 1

5 pages, 600 KiB  
Communication
Synthesis of 5-Aroyl-2-aryl-3-hydroxypyridin-4(1H)-ones
by Elena V. Steparuk, Dmitrii L. Obydennov and Vyacheslav Y. Sosnovskikh
Molbank 2023, 2023(2), M1668; https://doi.org/10.3390/M1668 - 10 Jun 2023
Cited by 2 | Viewed by 1158
Abstract
A two-stage synthesis of 5-aroyl-2-aryl-3-hydroxypyridin-4(1H)-ones (56–66% overall yields) was carried out by refluxing 5-aroyl-3-(benzyloxy)-2-(het)aryl-4H-pyran-4-ones with ammonium acetate in AcOH and subsequent debenzylation. The prepared N-unsubstituted 4-pyridones exist in the pyridone tautomeric form. Full article
Show Figures

Graphical abstract

4 pages, 321 KiB  
Short Note
5,6-Dihydro-[1,2,5]oxadiazolo[3,4-d]pyridazine-4,7-dione
by Timofey N. Chmovzh, Karim S. Gaisin and Oleg A. Rakitin
Molbank 2023, 2023(2), M1649; https://doi.org/10.3390/M1649 - 18 May 2023
Viewed by 1160
Abstract
1,2,5-Chalcogenadiazoles fused with electron-withdrawing heterocycles have been actively investigated for the preparation of organic photovoltaic materials. [1,2,5]Oxadiazolo[3,4-d]pyridazines are much less studied than other chalcogenadiazolopyridazines due to their low availability. In this communication, we report our study showing that 5,6-dihydro-[1,2,5]oxadiazolo[3,4-d]pyridazine-4,7-dione, a key precursor for [...] Read more.
1,2,5-Chalcogenadiazoles fused with electron-withdrawing heterocycles have been actively investigated for the preparation of organic photovoltaic materials. [1,2,5]Oxadiazolo[3,4-d]pyridazines are much less studied than other chalcogenadiazolopyridazines due to their low availability. In this communication, we report our study showing that 5,6-dihydro-[1,2,5]oxadiazolo[3,4-d]pyridazine-4,7-dione, a key precursor for the synthesis of 4,7-dihalo-[1,2,5]oxadiazolo[3,4-d]pyridazines, is formed via the cyclization of 1,2,5-oxadiazole-3,4-dicarbohydrazide in hydrochloric acid. The structure of the newly synthesized compound was established by means of elemental analysis; high-resolution mass spectrometry; 1H and 13C NMR; IR spectroscopy, and mass spectrometry. Full article
Show Figures

Graphical abstract

6 pages, 1690 KiB  
Short Note
5-(4-Chlorophenyl)-N,1-di-o-tolyl-1H-imidazole-2-amine
by Francesco Messa, Paride Papadia, Serena Perrone and Antonio Salomone
Molbank 2023, 2023(2), M1648; https://doi.org/10.3390/M1648 - 17 May 2023
Viewed by 1162
Abstract
A new 2-amino imidazole derivative, 5-(4-chlorophenyl)-N,1-di-o-tolyl-1H-imidazole-2-amine (3), has been synthesized using a green approach. The reaction was conducted in a ChCl (cholinium chloride)/urea eutectic mixture, which is a nature-inspired and environmentally friendly reaction medium. The proposed reaction mechanism involves [...] Read more.
A new 2-amino imidazole derivative, 5-(4-chlorophenyl)-N,1-di-o-tolyl-1H-imidazole-2-amine (3), has been synthesized using a green approach. The reaction was conducted in a ChCl (cholinium chloride)/urea eutectic mixture, which is a nature-inspired and environmentally friendly reaction medium. The proposed reaction mechanism involves the preliminary regioselective alkylation of the Nsp2 of guanidine (2), followed by an intramolecular condensation between the carbonyl moiety and the secondary N′sp3. Finally, a tautomerization/aromatization step furnished the final product (3). Notably, 2-amino imidazole (3) could be isolated in high yield (91%), just by filtration from the DES/water mixture and subsequent crystallization; the remaining ChCl/urea could be recycled, after water removal, for four consecutive reactions without any significant drop in the (3) yield. The product has been fully characterized by 1H, 13C, 2D 1H-13C HSQC, and 2D 1H-13C HMBC NMR; FT-IR spectroscopy; and EI-MS spectrometry. Full article
Show Figures

Figure 1

5 pages, 517 KiB  
Short Note
5-(1-(4-Hydroxy-6-methyl-2-oxo-2H-pyran-3-yl)-2-oxo-2-phenylethyl)-1,3-dimethylpyrimidine-2,4,6(1H,3H,5H)-trione
by Yuliya E. Ryzhkova, Varvara M. Kalashnikova, Fedor V. Ryzhkov and Michail N. Elinson
Molbank 2023, 2023(2), M1640; https://doi.org/10.3390/M1640 - 8 May 2023
Viewed by 1356
Abstract
Multicomponent reactions have been demonstrated as a promising tool for the creation of diverse molecular structures with enhanced efficiency, reduced waste, and a high atom economy. Arylglyoxal monohydrates with two different carbonyl groups are well known as worthwhile synthons in organic synthesis. 2-Pyrone [...] Read more.
Multicomponent reactions have been demonstrated as a promising tool for the creation of diverse molecular structures with enhanced efficiency, reduced waste, and a high atom economy. Arylglyoxal monohydrates with two different carbonyl groups are well known as worthwhile synthons in organic synthesis. 2-Pyrone and pyrimidine-2,4,6-trione are versatile building blocks for the synthesis of key intermediates in synthetic organic chemistry as well as in medicinal chemistry. A simple and efficient tandem Knoevenagel–Michael protocol for the synthesis of the previously unknown 5-(1-(4-hydroxy-6-methyl-2-oxo-2H-pyran-3-yl)-2-oxo-2-phenylethyl)-1,3-dimet-hylpyrimidine-2,4,6(1H,3H,5H)-trione was elaborated. The suggested method is based on the multicomponent reaction of phenylglyoxal hydrate, 1,3-dimethylbarbituric acid, and 4-hydroxy-6-methyl-2H-pyran-2-one. The structure of the synthesized compound was proven by 1H, 13C-NMR, and IR spectroscopy, mass spectrometry, and elemental analysis. A procedure for predicting the possible types of its biological activity was carried out for the title compound. Full article
Show Figures

Scheme 1

5 pages, 1560 KiB  
Short Note
N-[1-(2-Chlorophenyl)-2-{1-methyl-5-nitro-4-[(phenylsulfonyl)methyl]-1H-imidazol-2-yl}ethyl]-4-methylbenzenesulfonamide
by Romain Paoli-Lombardo, Nicolas Primas, Caroline Castera-Ducros, Inès Jacquet, Pascal Rathelot and Patrice Vanelle
Molbank 2023, 2023(2), M1633; https://doi.org/10.3390/M1633 - 25 Apr 2023
Viewed by 1059
Abstract
In continuation of our research program to develop original synthetic methods using TDAE methodology on nitroheterocyclic substrates, we were able to generate for the first time a stable carbanion in position 2 of the 5-nitroimidazole scaffold. Starting from a 2-chloromethyl-4-phenylsulfonylmethyl-5-nitroimidazole intermediate, prepared by [...] Read more.
In continuation of our research program to develop original synthetic methods using TDAE methodology on nitroheterocyclic substrates, we were able to generate for the first time a stable carbanion in position 2 of the 5-nitroimidazole scaffold. Starting from a 2-chloromethyl-4-phenylsulfonylmethyl-5-nitroimidazole intermediate, prepared by the vicarious nucleophilic substitution of hydrogen (VNS) reaction, we selectively introduced a N-tosylbenzylimine moiety at position 2 without reducing the sulfone at position 4, leading to the formation of N-[1-(2-chlorophenyl)-2-{1-methyl-5-nitro-4-[(phenylsulfonyl)methyl]-1H-imidazol-2-yl}ethyl]-4-methylbenzenesulfonamide in 47% yield. This new synthetic method using TDAE should allow access to new 2-substituted 5-nitroimidazole derivatives with various electrophiles such as carbonyls and other N-tosylbenzylimines. Full article
Show Figures

Figure 1

4 pages, 783 KiB  
Short Note
9-Methoxynaphtho[1,2-b]benzofuran
by Roberto Miani, Jacopo Vigna and Ines Mancini
Molbank 2023, 2023(2), M1632; https://doi.org/10.3390/M1632 - 25 Apr 2023
Cited by 1 | Viewed by 1038
Abstract
A highly selective one-pot microwave-assisted synthesis of 9-methoxynaphtho[1,2-b]benzofuran was obtained by treating 1-naphthol with 1-bromo-4-methoxy-2-nitrobenzene and two molar equivalents of potassium tert-butoxide in dimethyl sulfoxide. The selectivity in the production of the title compound was addressed by the suitable position [...] Read more.
A highly selective one-pot microwave-assisted synthesis of 9-methoxynaphtho[1,2-b]benzofuran was obtained by treating 1-naphthol with 1-bromo-4-methoxy-2-nitrobenzene and two molar equivalents of potassium tert-butoxide in dimethyl sulfoxide. The selectivity in the production of the title compound was addressed by the suitable position of the bromine and nitro group on the aryl reagent. Moreover, we highlight how the nitro group plays a dual role, as activator in the first nucleophilic substitution with the release of bromide ion and then as the leaving group in the furan cyclization. Eventually, the product was structurally characterized by MS and extensive NMR analyses. Full article
Show Figures

Scheme 1

5 pages, 1135 KiB  
Short Note
2-(2,5-Dimethoxyphenyl)pyrrole-3-carbonitrile
by Yannic Grimm, Dieter Schollmeyer and Heiner Detert
Molbank 2023, 2023(2), M1627; https://doi.org/10.3390/M1627 - 20 Apr 2023
Viewed by 1247
Abstract
The Cadogan reaction of 2-aryl-3-nitropyridines leads to δ-carbolines. The title compound is a side product in this reaction, generated via a ring opening of a nitrene and cyclization. A crystal structure analysis gives an enormous unit cell. Full article
Show Figures

Figure 1

8 pages, 3193 KiB  
Communication
3a-(4-Chlorophenyl)-1-methyl-3a,4-dihydroimidazo[1,5-a]quinazolin-5(3H)-one: Synthesis and In Silico Evaluation as a Ligand in the µ-Opioid Receptor
by Andrea Defant, Nicole Innocenti and Ines Mancini
Molbank 2023, 2023(2), M1622; https://doi.org/10.3390/M1622 - 17 Apr 2023
Cited by 1 | Viewed by 1209
Abstract
In the search for fused heterocycle molecules with potential biological activities, the new title compound was produced in racemic form via a four step-synthetic sequence with an overall yield of 60%. It was structurally characterised via 1H-, 13C-NMR and IR analyses, [...] Read more.
In the search for fused heterocycle molecules with potential biological activities, the new title compound was produced in racemic form via a four step-synthetic sequence with an overall yield of 60%. It was structurally characterised via 1H-, 13C-NMR and IR analyses, and the molecular composition was confirmed through a high-resolution MS experiment. After predicting its analgesic activity using PASS online software, wherein a good overlap between its enantiomers and the structure of the natural opioid morphine was observed, the compound was evaluated through docking calculations as a ligand of the µ-opioid receptor. The resulting energy values and interactions were comparable to the data obtained for morphine and its synthetic derivative fentanyl, which is used in the therapeutic treatment of severe forms of pain. Moreover, the title compound displayed favourable predicted blood–brain barrier permeation and drug-likeness. Full article
Show Figures

Figure 1

4 pages, 796 KiB  
Short Note
2-(3-Bromophenyl)imidazo[2,1-b]oxazole
by Ángel Cores, Mercedes Villacampa and J. Carlos Menéndez
Molbank 2023, 2023(2), M1616; https://doi.org/10.3390/M1616 - 4 Apr 2023
Viewed by 1226
Abstract
The microwave-assisted reaction of 2-nitroimidazole with 3-bromophenacyl bromide in the presence of potassium carbonate as a base and dimethylformamide as a solvent afforded 2-(3-bromophenyl)imidazo[2,1-b]oxazole. The formation of this compound was explained via a domino mechanism comprising an initial N-alkylation reaction of [...] Read more.
The microwave-assisted reaction of 2-nitroimidazole with 3-bromophenacyl bromide in the presence of potassium carbonate as a base and dimethylformamide as a solvent afforded 2-(3-bromophenyl)imidazo[2,1-b]oxazole. The formation of this compound was explained via a domino mechanism comprising an initial N-alkylation reaction of the imidazole substrate, followed by the base-promoted deprotonation of the position adjacent to the carbonyl to give an enolate anion that finally cyclizes via an intramolecular SNAr reaction, with the loss of the nitro group as potassium nitrite. Then, the proposed 1-(3-bromophenacyl)-2-nitroimidazole intermediate could be isolated by reducing the reaction time and was shown to be a precursor of the imidazo[2,1-b]oxazole final product. Full article
Show Figures

Scheme 1

5 pages, 960 KiB  
Short Note
tert-Butyl (E)-3-oxo-2-(3-oxoisobenzofuran-1(3H)-ylidene)butanoate
by Alexandra S. Chechulina, Ekaterina A. Knyazeva, Bin Kan, Tainan Duan and Oleg A. Rakitin
Molbank 2023, 2023(2), M1614; https://doi.org/10.3390/M1614 - 30 Mar 2023
Viewed by 1311
Abstract
Non-fullerene acceptors have recently attracted much attention as components of organic solar cells. 1H-indene-1,3(2H)-dione is a key compound for the synthesis of the end-capping component of non-fullerene acceptors. In this communication, an intermediate for the synthesis of this compound, [...] Read more.
Non-fullerene acceptors have recently attracted much attention as components of organic solar cells. 1H-indene-1,3(2H)-dione is a key compound for the synthesis of the end-capping component of non-fullerene acceptors. In this communication, an intermediate for the synthesis of this compound, tert-butyl (E)-3-oxo-2-(3-oxoisobenzofuran-1(3H)-ylidene)butanoate, was prepared by the reaction between phthalic anhydride and tert-butyl acetoacetate. Further treatment with sodium methoxide in methanol led to the formation of 1H-indene-1,3(2H)-dione in a high yield. The structure of the newly synthesized compound was established by means of elemental analysis, high-resolution mass spectrometry, 1H, 13C NMR, IR spectroscopy, mass spectrometry and X-ray analysis. Full article
Show Figures

Graphical abstract

6 pages, 706 KiB  
Short Note
New 2-(2,4-Dihydroxyphenyl)benzimidazolines
by Yordan Stremski, Maria Bachvarova, Desislava Kirkova and Stela Statkova-Abeghe
Molbank 2023, 2023(1), M1602; https://doi.org/10.3390/M1602 - 10 Mar 2023
Viewed by 1165
Abstract
New 2-(2,4-dihydroxyphenyl)benzimidazolines are synthesized in an easily accessible approach. The method is based on the reaction of resorcinol with in situ-formed electrophilic N-ethoxycarbonylbenzimidazolium reagents. The structure of the two newly formed products was spectrally characterized by 1D and 2D NMR, IR, and [...] Read more.
New 2-(2,4-dihydroxyphenyl)benzimidazolines are synthesized in an easily accessible approach. The method is based on the reaction of resorcinol with in situ-formed electrophilic N-ethoxycarbonylbenzimidazolium reagents. The structure of the two newly formed products was spectrally characterized by 1D and 2D NMR, IR, and MS spectral analyses. Full article
Show Figures

Graphical abstract

3 pages, 321 KiB  
Short Note
4,4′-Difluoro-[3,3′-bi(1,2,5-oxadiazole)] 2,2′-Dioxide
by Natalia V. Obruchnikova and Oleg A. Rakitin
Molbank 2023, 2023(1), M1596; https://doi.org/10.3390/M1596 - 23 Feb 2023
Viewed by 1074
Abstract
1,2,5-Oxadiazole oxides (furoxans) are well known nitric oxide donors; among them, 4-fluorofuroxans have recently been found to be important photoinduced nitric oxide donors. In this research, it was shown that the reaction of 4,4′-dinitro-[3,3′-bi(1,2,5-oxadiazole)] 2,2′-dioxide with fluoro-containing reagents (tetrabutylammonium fluoride or cesium fluoride) [...] Read more.
1,2,5-Oxadiazole oxides (furoxans) are well known nitric oxide donors; among them, 4-fluorofuroxans have recently been found to be important photoinduced nitric oxide donors. In this research, it was shown that the reaction of 4,4′-dinitro-[3,3′-bi(1,2,5-oxadiazole)] 2,2′-dioxide with fluoro-containing reagents (tetrabutylammonium fluoride or cesium fluoride) selectively gave the bis-substitution product 4,4′-difluoro-[3,3′-bi(1,2,5-oxadiazole)] 2,2′-dioxide. The structure of the synthesized compound was established by elemental analysis, 13C, 19F-NMR and IR spectroscopy, and mass-spectrometry. Full article
Show Figures

Scheme 1

7 pages, 2512 KiB  
Short Note
(E)-1-(5-Methyl-1-(4-nitrophenyl)-1H-1,2,3-triazol-4-yl)ethan-1-one Oxime
by Bakr F. Abdel-Wahab, Abdelbasset A. Farahat, Benson M. Kariuki and Gamal A. El-Hiti
Molbank 2023, 2023(1), M1593; https://doi.org/10.3390/M1593 - 21 Feb 2023
Cited by 3 | Viewed by 1376
Abstract
The reaction of 1-(5-methyl-1-(4-nitrophenyl)-1H-1,2,3-triazol-4-yl)ethan-1-one (1) with excess hydroxylamine hydrochloride (2 mole equivalents) in dry ethanol afforded (E)-1-(5-methyl-1-(4-nitrophenyl)-1H-1,2,3-triazol-4-yl)ethan-1-one oxime (2) in 86% yield. The structure of the new heterocycle 2 was confirmed using nuclear magnetic resonance spectroscopy, single crystal X-ray and elemental analysis. Full article
Show Figures

Graphical abstract

7 pages, 1807 KiB  
Short Note
Triethylammonium 2-(3-Hydroxy-2-oxoindolin-3-yl)-5,5-dimethyl-3-oxocyclohex-1-en-1-olate
by Yuliya E. Ryzhkova, Fedor V. Ryzhkov and Michail N. Elinson
Molbank 2023, 2023(1), M1589; https://doi.org/10.3390/M1589 - 15 Feb 2023
Cited by 1 | Viewed by 1284
Abstract
In recent years, the application of privileged structures has become a powerful approach in the discovery of new biologically active molecules. Ion pairing is a strategy used to enhance the permeation of ionized topical drugs. A convenient and efficient method for the synthesis [...] Read more.
In recent years, the application of privileged structures has become a powerful approach in the discovery of new biologically active molecules. Ion pairing is a strategy used to enhance the permeation of ionized topical drugs. A convenient and efficient method for the synthesis of triethylammonium 2-(3-hydroxy-2-oxoindolin-3-yl)-5,5-dimethyl-3-oxocyclohex-1-en-1-olate has been developed. The presented protocol includes an aldol reaction and the formation of an ammonium salt. Triethylamine is both a reactant and a catalyst in the process. The structure of the synthesized title compound has been established by 1H, 13C-NMR and IR spectroscopy, mass spectrometry, and elemental analysis. Full article
Show Figures

Graphical abstract

4 pages, 1133 KiB  
Short Note
4-Benzoyl-2-(4-bromophenyl)-1-(4-methoxyphenyl)-1,2-dihydropyrimidino[4,3-c][1,4]benzoxazine-3,5-dione
by Ekaterina E. Khramtsova, Maksim V. Dmitriev and Andrey N. Maslivets
Molbank 2023, 2023(1), M1583; https://doi.org/10.3390/M1583 - 8 Feb 2023
Viewed by 1181
Abstract
The reaction of 3-benzoylpyrrolo[2,1-c][1,4]benzoxazin-1,2,4-trione with N-(4-bromophenyl)-1-(4-methoxyphenyl)methanimine under thermolytical conditions afforded 4-benzoyl-2-(4-bromophenyl)-1-(4-methoxyphenyl)-1,2-dihydropyrimidino[4,3-c][1,4]benzoxazine-3,5-dione in a good yield. The reaction proceeded via in situ generation of a reactive intermediate, acyl(imidoyl)ketene. The compound was fully characterized. Full article
Show Figures

Figure 1

10 pages, 2059 KiB  
Short Note
(Z)-3-(Dicyanomethylene)-4-((5-fluoro-3,3-dimethyl-1-(3-phenylpropyl)-3H-indol-1-ium-2-yl) methylene)-2-(((E)-5-fluoro-3,3-dimethyl-1-(3-phenylpropyl)indolin-2-ylidene)methyl) cyclobut-1-en-1-olate
by Stefanie Casa, Guliz Ersoy Ozmen and Maged Henary
Molbank 2023, 2023(1), M1576; https://doi.org/10.3390/M1576 - 3 Feb 2023
Cited by 1 | Viewed by 1398
Abstract
Recent literature on this topic highlights the significance of adding malononitrile moiety and halogen substituents to the squaraine scaffold to create redshifted fluorophores into the near-infrared optical region. Herein, a redshifted hydrophobic squaraine dye is synthesized via a three-step pathway. The reported dye [...] Read more.
Recent literature on this topic highlights the significance of adding malononitrile moiety and halogen substituents to the squaraine scaffold to create redshifted fluorophores into the near-infrared optical region. Herein, a redshifted hydrophobic squaraine dye is synthesized via a three-step pathway. The reported dye is characterized by spectroscopic techniques, such as 1H NMR, 19F NMR, 13C NMR, and high-resolution mass spectroscopy. Optical properties are also reported using absorbance and fluorescence studies. The hydrophobicity of the dye was studied with absorbance and fluorescence spectroscopy in water–methanol mixtures and showed J-aggregates as the water concentration increased. Density functional theory calculations were conducted to assess its electron delocalization as well as observe the three-dimensional geometry of the dye as a result of the dicyanomethylene modification and the two bulky phenyl groups. Full article
Show Figures

Graphical abstract

7 pages, 1071 KiB  
Short Note
6-Chloro-3-nitro-2-[(phenylsulfonyl)methyl]imidazo[1,2-b]pyridazine
by Romain Paoli-Lombardo, Nicolas Primas, Sébastien Hutter, Sandra Bourgeade-Delmas, Clotilde Boudot, Caroline Castera-Ducros, Inès Jacquet, Bertrand Courtioux, Nadine Azas, Pascal Rathelot and Patrice Vanelle
Molbank 2023, 2023(1), M1573; https://doi.org/10.3390/M1573 - 1 Feb 2023
Viewed by 1276
Abstract
As part of our ongoing scaffold-hopping work on an antikinetoplastid 3-nitroimidazo[1,2-a]pyridine scaffold, we explored 3-nitroimidazo[1,2-b]pyridazine as a potential new antikinetoplastid series. Using conditions previously described by our lab, we obtained 6-chloro-3-nitro-2-[(phenylsulfonyl)methyl]imidazo[1,2-b]pyridazine with 54% yield. In vitro activity [...] Read more.
As part of our ongoing scaffold-hopping work on an antikinetoplastid 3-nitroimidazo[1,2-a]pyridine scaffold, we explored 3-nitroimidazo[1,2-b]pyridazine as a potential new antikinetoplastid series. Using conditions previously described by our lab, we obtained 6-chloro-3-nitro-2-[(phenylsulfonyl)methyl]imidazo[1,2-b]pyridazine with 54% yield. In vitro activity of this compound was evaluated against both the promastigote form of Leishmania donovani, the axenic amastigote form of Leishmania infantum and the trypomastigote blood stream form of Trypanosomabrucei brucei, and its influence on cell viability was assessed on the HepG2 cell line. However, despite good activity against the trypomastigote blood stream form of T. b. brucei (EC50 = 0.38 µM), it showed poor solubility in both HepG2 (CC50 > 7.8 µM) and L. infantum axenic amastigotes (EC50 > 1.6 µM) culture media, associated with a loss of activity against the promastigote form of L. infantum (EC50 > 15.6 µM). Full article
Show Figures

Figure 1

6 pages, 1118 KiB  
Communication
(3-(1H-Indol-3-yl)-2-(7,8,12,13-tetraoxa-10-azaspiro[5.7]tridecan-10-yl)propanoic acid) with Cytotoxic Activity
by Nataliya N. Makhmudiyarova, Irina R. Ishmukhametova, Lilya U. Dzhemileva and Usein M. Dzhemilev
Molbank 2023, 2023(1), M1572; https://doi.org/10.3390/M1572 - 1 Feb 2023
Viewed by 1095
Abstract
An efficient method for the synthesis of 3-(1H-indol-3-yl)-2-(7,8,12,13-tetraoxa-10-azaspiro[5.7]tridecan-10-yl)propanoic acid) via condensation of 7,8,10,12,13-pentaoxaspiro[5.7]tridecane with tryptophan under the action of a catalyst based on Sm(NO3)3·6H2O has been developed. A high cytotoxic activity of eight-membered azadiperoxide against [...] Read more.
An efficient method for the synthesis of 3-(1H-indol-3-yl)-2-(7,8,12,13-tetraoxa-10-azaspiro[5.7]tridecan-10-yl)propanoic acid) via condensation of 7,8,10,12,13-pentaoxaspiro[5.7]tridecane with tryptophan under the action of a catalyst based on Sm(NO3)3·6H2O has been developed. A high cytotoxic activity of eight-membered azadiperoxide against tumor cells Jurkat, K562, U937, and HL60 was established. Additionally, this compound is an inducer of apoptosis and affects the cell cycle. Full article
Show Figures

Figure 1

4 pages, 523 KiB  
Short Note
2-{9-(10-Bromoanthracenyl)}-1,3-dihydro-1H-[d]-1,3,2-benzodiazaborole
by Siphamandla Sithebe
Molbank 2023, 2023(1), M1569; https://doi.org/10.3390/M1569 - 27 Jan 2023
Viewed by 1083
Abstract
In this paper, a synthesis and characterization of a novel three coordinate 2-{9-(10-Bromoanthracenyl)}-1,3-dihydro-1H-[d]-1,3,2-benzodiazaborole from a cyclo-condensation reaction of o-phenylenediamine and 10-bromoanthracene-9-boronic acid is described. The desired product was obtained in 0.343 g (92% yields) with its structure characterized [...] Read more.
In this paper, a synthesis and characterization of a novel three coordinate 2-{9-(10-Bromoanthracenyl)}-1,3-dihydro-1H-[d]-1,3,2-benzodiazaborole from a cyclo-condensation reaction of o-phenylenediamine and 10-bromoanthracene-9-boronic acid is described. The desired product was obtained in 0.343 g (92% yields) with its structure characterized by 1H, 11B, 13C NMR, HRMS and FT-IR. Full article
Show Figures

Scheme 1

7 pages, 762 KiB  
Communication
Synthesis of Pentacycloundecane (PCUD) Based Spiro-Pyrano-Cage Framework via Ring-Closing Metathesis
by Sambasivarao Kotha, Mohammad Salman and Subba Rao Cheekatla
Molbank 2023, 2023(1), M1567; https://doi.org/10.3390/M1567 - 23 Jan 2023
Cited by 1 | Viewed by 1506
Abstract
Here, we demonstrate a short synthetic route to pyrano cage systems containing pentacycloundecane units by employing ring-closing metathesis (RCM) as a key step. These cage systems were constructed starting with readily available starting materials by adopting atomic economic processes such as cycloadditions (Diels-Alder [...] Read more.
Here, we demonstrate a short synthetic route to pyrano cage systems containing pentacycloundecane units by employing ring-closing metathesis (RCM) as a key step. These cage systems were constructed starting with readily available starting materials by adopting atomic economic processes such as cycloadditions (Diels-Alder reaction and [2+2] cycloaddition), Grignard addition, and olefin metathesis. The key building block, such as hexacyclic cage dione, was prepared from 1,4-naphthoquinone derivative and freshly cracked 1,3-cyclopentadiene. Some of these heterocyclic motifs are useful in biological chemistry and valuable as key synthons for high-energy-density materials. Full article
Show Figures

Figure 1

7 pages, 720 KiB  
Communication
Synthesis of Bis(1,2,3-triazolyl)alkanes in Superbasic and Solvent-Free Conditions
by Roman D. Marchenko and Andrei S. Potapov
Molbank 2023, 2023(1), M1551; https://doi.org/10.3390/M1551 - 13 Jan 2023
Viewed by 1304
Abstract
Nucleophilic substitution reactions between 1,2,3-triazole and dibromomethane or 1,2-dirbomoethane in a superbasic medium potassium hydroxide–dimethyl sulfoxide gave mixtures of the isomeric bis(1,2,3-triazolyl)alkanes, in which (1,2,3-triazol-1-yl)(1,2,3-triazol-2-yl)alkanes and bis(1,2,3-triazol-2-yl)alkanes were the dominating products, while bis(triazol-1-yl)alkanes were detected only in trace amounts. The same products could [...] Read more.
Nucleophilic substitution reactions between 1,2,3-triazole and dibromomethane or 1,2-dirbomoethane in a superbasic medium potassium hydroxide–dimethyl sulfoxide gave mixtures of the isomeric bis(1,2,3-triazolyl)alkanes, in which (1,2,3-triazol-1-yl)(1,2,3-triazol-2-yl)alkanes and bis(1,2,3-triazol-2-yl)alkanes were the dominating products, while bis(triazol-1-yl)alkanes were detected only in trace amounts. The same products could also be obtained under solvent-free conditions in a neat reaction mixture. The proposed methods are economically feasible, do not require using toxic solvents or catalysts, and make the (1,2,3-triazol-2-yl)-derivatives, inaccessible by alkyne-azide cycloaddition (click) reactions, readily available. Full article
Show Figures

Graphical abstract

8 pages, 1542 KiB  
Short Note
2,4-Diamino-5-(5-hydroxy-1-phenyl-3-(trifluoromethyl)-1H-pyrazol-4-yl)-5H-chromeno[2,3-b]pyridine-3-carbonitrile
by Yuliya E. Ryzhkova, Fedor V. Ryzhkov, Oleg I. Maslov and Michail N. Elinson
Molbank 2023, 2023(1), M1541; https://doi.org/10.3390/M1541 - 9 Jan 2023
Viewed by 1263
Abstract
5H-Chromeno[2,3-b]pyridines are important compounds with industrial, biological, and medicinal properties. In this short note, the multicomponent reaction of salicylaldehyde, malononitrile dimer, and 2-phenyl-5-(trifluoromethyl)-2,4-dihydro-3H-pyrazol-3-one in dimethyl sulfoxide at ambient temperature was investigated to give 2,4-diamino-5-(5-hydroxy-1-phenyl-3-(trifluoromethyl)-1H-pyrazol-4-yl)-5H [...] Read more.
5H-Chromeno[2,3-b]pyridines are important compounds with industrial, biological, and medicinal properties. In this short note, the multicomponent reaction of salicylaldehyde, malononitrile dimer, and 2-phenyl-5-(trifluoromethyl)-2,4-dihydro-3H-pyrazol-3-one in dimethyl sulfoxide at ambient temperature was investigated to give 2,4-diamino-5-(5-hydroxy-1-phenyl-3-(trifluoromethyl)-1H-pyrazol-4-yl)-5H-chromeno[2,3-b]pyridine-3-carbonitrile with good yield. The structure of the previously unknown chromeno[2,3-b]pyridine derivative was confirmed by elemental analysis, mass, nuclear magnetic resonance, and infrared spectroscopy data. The ADME (absorption, distribution, metabolism, and excretion) properties were also assessed. Full article
Show Figures

Graphical abstract

2022

Jump to: 2024, 2023, 2021, 2020, 2019

6 pages, 1729 KiB  
Short Note
2-[2-(Diphenylphosphoryl)phenyl]-1H-perimidine
by Mangaliso N. Goge, Siphamandla Sithebe and Tshephiso R. Papo
Molbank 2023, 2023(1), M1537; https://doi.org/10.3390/M1537 - 29 Dec 2022
Cited by 1 | Viewed by 1364
Abstract
In this paper, we report the crystal structure of 2-[2-(diphenylphosphoryl)phenyl]-1H-perimidine (L1) obtained from the ring closure reaction of 1,8-diaminonaphthalene and 2-(diphenylphosphino)benzaldehyde, followed by the dehydrogenation reaction with sodium metabisulfite (Na2S2O5). L1 was characterised using 1H, 13 [...] Read more.
In this paper, we report the crystal structure of 2-[2-(diphenylphosphoryl)phenyl]-1H-perimidine (L1) obtained from the ring closure reaction of 1,8-diaminonaphthalene and 2-(diphenylphosphino)benzaldehyde, followed by the dehydrogenation reaction with sodium metabisulfite (Na2S2O5). L1 was characterised using 1H, 13C & 31P NMR, FT-IR and X-ray single structure analyses. Full article
Show Figures

Figure 1

5 pages, 1992 KiB  
Communication
1-(4-{[3,5-bis({[3,5-Dimethyl-4-(4-methyl-3,5-dioxo-1,2,4-triazolidin-1-yl)-phenoxy]methyl})phenyl]methoxy}-2,6-dimethyl-phenyl)-4-methyl-1,2,4-triazolidine-3,5-dione
by Gary W. Breton and James Alexander Bowron, Jr.
Molbank 2023, 2023(1), M1535; https://doi.org/10.3390/M1535 - 27 Dec 2022
Cited by 1 | Viewed by 1078
Abstract
Appropriately substituted N-centered urazolyl radicals are capable of generating interesting cage-like structures upon forming N-N bonds. The radicals are generated by the oxidation of the corresponding NH urazole precursors. We synthesized a triurazole precursor that we hoped would dimerize through the formation of [...] Read more.
Appropriately substituted N-centered urazolyl radicals are capable of generating interesting cage-like structures upon forming N-N bonds. The radicals are generated by the oxidation of the corresponding NH urazole precursors. We synthesized a triurazole precursor that we hoped would dimerize through the formation of three N-N bonds to afford a large molecular cage. Unfortunately, the attempts at the oxidation of the urazoles to form urazolyl radicals instead only lead to random oligomerization, forming plastic-like materials rather than the desired cages. Full article
Show Figures

Figure 1

9 pages, 838 KiB  
Short Note
1-[2-(1H-Pyrrole-2-carbonyl)phenyl]-3-(4-methoxyphenyl)urea
by Antonia G. Sarantou and George Varvounis
Molbank 2023, 2023(1), M1531; https://doi.org/10.3390/M1531 - 22 Dec 2022
Viewed by 1658
Abstract
For the synthesis of 1-(2-(1H-pyrrole-2-carbonyl)phenyl)-3-(4-methoxyphenyl)urea, the final product, two different methods were used, in one or two steps, from (2-aminophenyl)(1H-pyrrol-2-yl)methanone. The one-step synthesis entailed a carbonylation reaction with 1/3 equivalent of triphosgene in the presence of two equivalents of [...] Read more.
For the synthesis of 1-(2-(1H-pyrrole-2-carbonyl)phenyl)-3-(4-methoxyphenyl)urea, the final product, two different methods were used, in one or two steps, from (2-aminophenyl)(1H-pyrrol-2-yl)methanone. The one-step synthesis entailed a carbonylation reaction with 1/3 equivalent of triphosgene in the presence of two equivalents of trimethylamine, followed by the addition of 4-methoxyaniline to the in situ generated aryl isocyanate. The two-step synthesis required first the preparation of phenyl(2-(1H-pyrrole-2-carbonyl)phenyl)carbamate and then a substitution reaction by 4-methoxyaniline. The first method produced the final product in 72% yield, which was the best yield. The structure of the final product was confirmed by FTIR, UV-VIS, 1H and 13C NMR spectroscopy and high resolution mass spectrometry. Full article
Show Figures

Figure 1

7 pages, 729 KiB  
Short Note
2-Benzyl-3-morpholino-7-(thiophen-2-yl)-6-(thiophen-2-ylmethyl)-6,7-dihydro-5H-pyrrolo[3,4-b]pyridin-5-one
by Ivette Morales-Salazar, Mónica A. Rincón-Guevara, Eduardo González-Zamora and Alejandro Islas-Jácome
Molbank 2022, 2022(4), M1503; https://doi.org/10.3390/M1503 - 23 Nov 2022
Cited by 1 | Viewed by 1188
Abstract
The new polyheterocyclic compound 2-benzyl-3-morpholino-7-(thiophen-2-yl)-6-(thiophen-2-ylmethyl)-6,7-dihydro-5H-pyrrolo[3,4-b]pyridin-5-one (1) was synthesized via a one-pot process involving an Ugi-Zhu three-component reaction coupled to a cascade aza-Diels-Alder cycloaddition/N-acylation/decarboxylation/dehydration process, using toluene as the solvent, ytterbium (III) triflate as the [...] Read more.
The new polyheterocyclic compound 2-benzyl-3-morpholino-7-(thiophen-2-yl)-6-(thiophen-2-ylmethyl)-6,7-dihydro-5H-pyrrolo[3,4-b]pyridin-5-one (1) was synthesized via a one-pot process involving an Ugi-Zhu three-component reaction coupled to a cascade aza-Diels-Alder cycloaddition/N-acylation/decarboxylation/dehydration process, using toluene as the solvent, ytterbium (III) triflate as the Lewis acid catalyst, and microwave-dielectric heating to increase the overall yield by up to 73%, while decreasing the reaction time to less than one hour. Product 1 was fully characterized by its physicochemical properties and using spectroscopic techniques (IR, HRMS and NMR). Full article
Show Figures

Graphical abstract

7 pages, 1786 KiB  
Short Note
4-Methyl-7-((2-((5-methyl-1,3,4-thiadiazol-2-yl)thio)ethyl)thio)-coumarin
by Vanya Kurteva, Rusi Rusew and Boris Shivachev
Molbank 2022, 2022(4), M1491; https://doi.org/10.3390/M1491 - 12 Nov 2022
Cited by 1 | Viewed by 1463
Abstract
The novel compound 4-methyl-7-((2-((5-methyl-1,3,4-thiadiazol-2-yl)thio)ethyl)thio)-coumarin is obtained in good yield via a two-step protocol; that is, initial synthesis of the reagent 2-((2-chloroethyl)thio)-5-methyl-1,3,4-thiadiazole followed by alkylation of 7-mercapto-4-methylcoumarin. The product’s structure is assigned by 1D and 2D NMR experiments and is confirmed by single-crystal XRD. [...] Read more.
The novel compound 4-methyl-7-((2-((5-methyl-1,3,4-thiadiazol-2-yl)thio)ethyl)thio)-coumarin is obtained in good yield via a two-step protocol; that is, initial synthesis of the reagent 2-((2-chloroethyl)thio)-5-methyl-1,3,4-thiadiazole followed by alkylation of 7-mercapto-4-methylcoumarin. The product’s structure is assigned by 1D and 2D NMR experiments and is confirmed by single-crystal XRD. Full article
Show Figures

Figure 1

6 pages, 812 KiB  
Short Note
5-Chloro-6-oxo-6H-xantheno[4,3-d]thiazole-2-carbonitrile
by Konstantinos Paraskevas, Christos Iliopoulos-Tsoutsouvas, Eleftheria A. Georgiou and Ioannis K. Kostakis
Molbank 2022, 2022(4), M1489; https://doi.org/10.3390/M1489 - 10 Nov 2022
Viewed by 1496
Abstract
Xanthones and benzothiazoles are important classes of heterocyclic compounds with versatile biological activities. Herein, we describe a straightforward and scalable synthesis of 5-chloro-6-oxo-6H-xantheno[4,3-d]thiazole-2-carbonitrile, a thiazole-fused xanthone, via a six-step approach, using Appel’s salt for the synthesis of the thiazole [...] Read more.
Xanthones and benzothiazoles are important classes of heterocyclic compounds with versatile biological activities. Herein, we describe a straightforward and scalable synthesis of 5-chloro-6-oxo-6H-xantheno[4,3-d]thiazole-2-carbonitrile, a thiazole-fused xanthone, via a six-step approach, using Appel’s salt for the synthesis of the thiazole ring. The thiazole-fused xanthone was fully characterized employing 1H and 13C NMR spectra, using direct and long-range heteronuclear correlation experiments (HMBC and HMQC). Full article
Show Figures

Graphical abstract

8 pages, 2368 KiB  
Communication
Synthesis and Characterization of 3-Methyl-1-(4-(trifluoromethyl)phenyl)indeno [1,2-c]pyrazol-4(1H)-one
by Linh Lam, Sang H. Park and Joseph Sloop
Molbank 2022, 2022(4), M1483; https://doi.org/10.3390/M1483 - 7 Nov 2022
Viewed by 1793
Abstract
Pyrazoles have potential applications in the agrochemical and medicinal chemistry industries as pesticides, anti-inflammatory medications, and antitumor drugs. Fluorinated fused-ring pyrazoles may also possess medicinally useful properties. Herein, we report the acid-catalyzed synthesis of a new tricyclic, trifluoromethylated indenopyrazole, 3-methyl-1-(4-(trifluoromethyl)phenyl)indeno[1,2-c]pyrazol-4(1H)-one, from [...] Read more.
Pyrazoles have potential applications in the agrochemical and medicinal chemistry industries as pesticides, anti-inflammatory medications, and antitumor drugs. Fluorinated fused-ring pyrazoles may also possess medicinally useful properties. Herein, we report the acid-catalyzed synthesis of a new tricyclic, trifluoromethylated indenopyrazole, 3-methyl-1-(4-(trifluoromethyl)phenyl)indeno[1,2-c]pyrazol-4(1H)-one, from 2-acetyl-1,3-indanedione and 4-trifluoromethylphenylhydrazine. This isomeric pyrazole was obtained in yields ranging from 4–24%. NMR spectroscopic characterization and elemental analysis support the structural assignment, identity, and purity of the product. Full article
Show Figures

Figure 1

4 pages, 2070 KiB  
Short Note
Dimethyl 3,7-diamino-4,8-bis((2-methoxy-2-oxoethyl)thio)benzo[1,2-b:4,5-b’]dithiophene-2,6-dicarboxylate
by Branislav Pavilek, Daniel Végh, Dušan Bortňák, Veronika Šmejkalová, Jozef Kožíšek and Viktor Milata
Molbank 2022, 2022(4), M1474; https://doi.org/10.3390/M1474 - 27 Oct 2022
Viewed by 1234
Abstract
The convenient and multigram synthesis of a linear benzo[b]dithiophene (BDT) structure is proposed (dimethyl 3,7-diamino-4,8-bis((2-methoxy-2-oxoethyl)thio)benzo[1,2-b:4,5-b’]dithiophene-2,6-dicarboxylate). The starting materials are commercially available 2,3,5,6-tetrachloroterephthalonitrile and methyl 2-mercaptoacetate, which undergo aromatic substitution, followed by a cyclization reaction in basic conditions [...] Read more.
The convenient and multigram synthesis of a linear benzo[b]dithiophene (BDT) structure is proposed (dimethyl 3,7-diamino-4,8-bis((2-methoxy-2-oxoethyl)thio)benzo[1,2-b:4,5-b’]dithiophene-2,6-dicarboxylate). The starting materials are commercially available 2,3,5,6-tetrachloroterephthalonitrile and methyl 2-mercaptoacetate, which undergo aromatic substitution, followed by a cyclization reaction in basic conditions to form suitable BDT for potential optoelectronic applications. Full article
Show Figures

Figure 1

4 pages, 577 KiB  
Short Note
1-Phenyl-3-tosyl-1H-pyrrole
by Zoumpoulia Kechagioglou and Vassilis J. Demopoulos
Molbank 2022, 2022(4), M1471; https://doi.org/10.3390/M1471 - 26 Oct 2022
Viewed by 1182
Abstract
1-Phenyl-3-tosyl-1H-pyrrole was prepared, in moderate yield, by the electrophilic aromatic substitution of 1-phenyl-1H-pyrrole with tosyl chloride in the presence of excess zinc oxide under solvent-free conditions. A minor product was its isomer, 1-phenyl-2-tosyl-1H-pyrrole. Full article
Show Figures

Scheme 1

7 pages, 738 KiB  
Short Note
3-Methyl 5-{3-[(4-Methylbenzenesulfonyl)oxy]propyl} 4-(2,3-Dichlorophenyl)-2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate
by Carlotta Borgarelli, Stijn Lenaers, Wim M. De Borggraeve and Ermal Ismalaj
Molbank 2022, 2022(4), M1460; https://doi.org/10.3390/M1460 - 9 Oct 2022
Viewed by 1508
Abstract
The 1,4-dihydropyridine is a ubiquitous scaffold employed not only in medicinal chemistry but also in organic synthesis, given its ability to act as a hydrogen transfer reagent, thus emulating NAD(P)H reducing agents. In this work, we describe the synthesis of 3-methyl 5-{3-[(4-methylbenzenesulfonyl)oxy]propyl} 4-(2,3-dichlorophenyl)-2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate [...] Read more.
The 1,4-dihydropyridine is a ubiquitous scaffold employed not only in medicinal chemistry but also in organic synthesis, given its ability to act as a hydrogen transfer reagent, thus emulating NAD(P)H reducing agents. In this work, we describe the synthesis of 3-methyl 5-{3-[(4-methylbenzenesulfonyl)oxy]propyl} 4-(2,3-dichlorophenyl)-2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate as scaffold, which enables downstream derivatization towards new 1,4-dihydropyridine molecules. Inspired by the literature, a new two-step synthesis was planned that involved: (i) synthesis of a silylated 1,4-dihydropyridine derivative and (ii) deprotection and tosylation in one step using tosyl fluoride. Full article
Show Figures

Figure 1

6 pages, 661 KiB  
Short Note
Ferrocenyl-bis-(1-(4-benzyl-5-morpholinooxazol-2-yl)-N-(4-(trifluoromethyl)benzyl)methanamine)
by Roberto E. Blanco-Carapia, Enrique A. Aguilar-Rangel, Alejandro Islas-Jácome and Eduardo González-Zamora
Molbank 2022, 2022(3), M1444; https://doi.org/10.3390/M1444 - 13 Sep 2022
Cited by 1 | Viewed by 1373
Abstract
The new bis-heterocyclic compound ferrocenyl-bis-(1-(4-benzyl-5-morpholinooxazol-2-yl)-N-(4-(trifluoromethyl)benzyl)methanamine) (1) was synthesized in 73% overall yield in 1.5 hours via a pseudo-repetitive Ugi-Zhu five-component reaction, starting from 1,1′-ferrocenedicarboxaldehyde, 4-(trifluoromethyl)benzylamine, and 2-isocyano-1-morpholino-3-phenylpropan-1-one, in 1:2.1:2.2 proportions, respectively, using scandium(III) triflate as a [...] Read more.
The new bis-heterocyclic compound ferrocenyl-bis-(1-(4-benzyl-5-morpholinooxazol-2-yl)-N-(4-(trifluoromethyl)benzyl)methanamine) (1) was synthesized in 73% overall yield in 1.5 hours via a pseudo-repetitive Ugi-Zhu five-component reaction, starting from 1,1′-ferrocenedicarboxaldehyde, 4-(trifluoromethyl)benzylamine, and 2-isocyano-1-morpholino-3-phenylpropan-1-one, in 1:2.1:2.2 proportions, respectively, using scandium(III) triflate as a Lewis-acid catalyst, microwaves as a heat source, and toluene as a solvent. The synthesized compound was characterized by 1D (1H, 13C, and 19F) and 2D (COSY, HSQC, and HMBC) NMR, HRMS, and FT-IR. Full article
Show Figures

Figure 1

9 pages, 612 KiB  
Short Note
1,1′-{[3,5-Bis((dodecyloxycarbonyl)-4-phenyl-1,4-dihydropyridine-2,6-diyl]bis(methylene)}bis[4-(anthracen-9-yl)pyridin-1-ium] Dibromide
by Reinis Ozolins, Mara Plotniece, Karlis Pajuste, Reinis Putralis, Nadiia Pikun, Arkadij Sobolev, Aiva Plotniece and Martins Rucins
Molbank 2022, 2022(3), M1438; https://doi.org/10.3390/M1438 - 2 Sep 2022
Cited by 3 | Viewed by 1759
Abstract
A synthesis of a cationic moiety and fluorescent moieties containing amphiphilic 1,4-dihydropyridine (1,4-DHP) derivatives was performed starting with the Hantzsch-type cyclization of dodecyl acetoacetate, phenylaldehyde and ammonium acetate. Bromination of the 2,6-dimethyl groups of a parent 1,4-DHP compound, followed by nucleophilic substitution of [...] Read more.
A synthesis of a cationic moiety and fluorescent moieties containing amphiphilic 1,4-dihydropyridine (1,4-DHP) derivatives was performed starting with the Hantzsch-type cyclization of dodecyl acetoacetate, phenylaldehyde and ammonium acetate. Bromination of the 2,6-dimethyl groups of a parent 1,4-DHP compound, followed by nucleophilic substitution of bromine with 4-(anthracen-9-yl)pyridine, produced the desired 1,1′-{[3,5-bis((dodecyloxycarbonyl)-4-phenyl-1,4-dihydropyridine-2,6-diyl]bis(methylene)}bis[4-(anthracen-9-yl)pyridin-1-ium] dibromide. The obtained target compound was fully characterized by the IR, 1H NMR, 13C NMR and HRMS data. Studies of the self-assembling properties and characterization of the nanoparticles obtained by the ethanol injection method were performed using dynamic light scattering (DLS) measurements. DLS measurement data showed that 1,1′-{[3,5-bis((dodecyloxycarbonyl)-4-phenyl-1,4-dihydropyridine-2,6-diyl]bis(methylene)}bis[4-(anthracen-9-yl)pyridin-1-ium] dibromide produced liposomes that had average diameters of 200 nm when the samples were freshly prepared, and 140 nm after 7 days or 1 month storage. The PDI values of the samples were approximately 0.50 and their zeta-potential values were approximately 41 mV when the samples were freshly prepared, and 33 mV after storage. The obtained nanoparticles were stored at room temperature for one month and remained stable during that period. The mean molecular area of the cationic 1,4-DHP-anthracene hybrid 4 was 118 Å2, while the mean molecular area of the cationic 1,4-DHP 5 without anthracene substituents was only 83 Å2. The photoluminescence quantum yield (PLQY) value for the EtOH solution of the 1,4-DHP derivative 4 was 10.8%, but for the 1,4-DHP derivative 5 it was only 1.8%. These types of compounds could be used as synthetic lipids in the further development of prospective theranostic delivery systems. Full article
Show Figures

Figure 1

4 pages, 926 KiB  
Short Note
3-(1-Cyclohexyl-2-(cyclohexylamino)-4-(4-ethoxyphenyl)-6-oxo-1,6-dihydropyrimidin-5-yl)-1-methylquinoxalin-2(1H)-one
by Ekaterina E. Khramtsova, Svetlana O. Kasatkina, Maksim V. Dmitriev and Andrey N. Maslivets
Molbank 2022, 2022(3), M1421; https://doi.org/10.3390/M1421 - 5 Aug 2022
Viewed by 1671
Abstract
The reaction of 3-cyclohexyl-2-(cyclohexylimino)-6-(4-ethoxyphenyl)-5-(4-methyl-3-oxo-3,4-dihydroquinoxalin-2-yl)-2,3-dihydro-4H-1,3-oxazin-4-one with ammonium acetate afforded 3-(1-cyclohexyl-2-(cyclohexylamino)-4-(4-ethoxyphenyl)-6-oxo-1,6-dihydropyrimidin-5-yl)-1-methylquinoxalin-2(1H)-one in a good yield. The compound was fully characterized. Full article
Show Figures

Figure 1

4 pages, 1408 KiB  
Short Note
12H-Dibenzo[d,g][1,2,3]triselenocin-12-ol
by Marko Boskovic, Stanislav Andreev, Dieter Schollmeyer and Pierre Koch
Molbank 2022, 2022(3), M1418; https://doi.org/10.3390/M1418 - 1 Aug 2022
Viewed by 1366
Abstract
Reaction of diphenylmethanol (4) with n-butyllithium and subsequent treatment with selenium resulted in 12H-dibenzo[d,g][1,2,3]triselenocin-12-ol (5) comprising a novel heterocyclic ring system. The title compound 5 was analyzed by 1H-NMR, 13C-NMR [...] Read more.
Reaction of diphenylmethanol (4) with n-butyllithium and subsequent treatment with selenium resulted in 12H-dibenzo[d,g][1,2,3]triselenocin-12-ol (5) comprising a novel heterocyclic ring system. The title compound 5 was analyzed by 1H-NMR, 13C-NMR and HPLC. Additionally, the structure of 5 was confirmed by single crystal X-ray diffraction. Full article
Show Figures

Figure 1

9 pages, 2000 KiB  
Short Note
3-Amino-4-(diphenylamino)-1H-2-benzopyran-1-one
by Felipe Quiroga-Suavita, Ricaurte Rodríguez and Omar León
Molbank 2022, 2022(3), M1408; https://doi.org/10.3390/M1408 - 14 Jul 2022
Viewed by 1525
Abstract
Various synthetic methodologies to obtain 3,4-diaminoisocumarin nucleus have been reported and described. However, mechanistic analysis based on experimental evidence is lacking. Herein, we report the synthesis of the novel 3-amino-4-(diphenylamino)-1H-2-benzopyran-1-one using a two-step methodology with a new mechanistic proposal to explain [...] Read more.
Various synthetic methodologies to obtain 3,4-diaminoisocumarin nucleus have been reported and described. However, mechanistic analysis based on experimental evidence is lacking. Herein, we report the synthesis of the novel 3-amino-4-(diphenylamino)-1H-2-benzopyran-1-one using a two-step methodology with a new mechanistic proposal to explain the formation of the latter based on previously reported precursors and the established conditions. This compound was afforded in 80% yield. Full article
Show Figures

Graphical abstract

7 pages, 2059 KiB  
Communication
Unexpected Formation of 4-[(1-Carbamoyl-3-oxo-1,3-dihydro-2-benzofuran-1-yl)amino]benzoic Acid from 4-[(3-Amino-1-oxo-1H-2-benzopyran-4-yl)amino]benzoic Acid
by Ricaurte Rodríguez, Felipe Quiroga-Suavita and Mónica Yadira Dotor Robayo
Molbank 2022, 2022(3), M1407; https://doi.org/10.3390/M1407 - 12 Jul 2022
Viewed by 1530
Abstract
With the aim of obtaining derivatives belonging to 2′,3′-diphenyl-3H-spiro[[2]benzofuran-1,4′-imidazole]-3,5′(3′H)-dione nucleus, we synthesized 4-[(3-amino-1-oxo-1H-2-benzopyran-4-yl)amino]benzoic acid (a 3,4-diaminoisocoumarine derivative), a known precursor of 4-[(1-carbamoyl-3-oxo-1,3-dihydro-2-benzofuran-1-yl)amino]benzoic acid (a phthalide–carboxamide-bearing system) by a novel methodology that we report here. The reaction conditions [...] Read more.
With the aim of obtaining derivatives belonging to 2′,3′-diphenyl-3H-spiro[[2]benzofuran-1,4′-imidazole]-3,5′(3′H)-dione nucleus, we synthesized 4-[(3-amino-1-oxo-1H-2-benzopyran-4-yl)amino]benzoic acid (a 3,4-diaminoisocoumarine derivative), a known precursor of 4-[(1-carbamoyl-3-oxo-1,3-dihydro-2-benzofuran-1-yl)amino]benzoic acid (a phthalide–carboxamide-bearing system) by a novel methodology that we report here. The reaction conditions were optimized to afford the latter in 62% yield. Full article
Show Figures

Graphical abstract

8 pages, 553 KiB  
Communication
Synthesis and Evaluation of Self-Assembling Properties of 3-(3,5-Difluoro-3,5-bis((alkoxy)carbonyl)-2,6-dioxoheptan-4-yl)-1-methylpyridin-1-ium Iodides
by Nadiia Pikun, Davis Lacis, Arkadij Sobolev, Martins Rucins, Mara Plotniece, Karlis Pajuste and Aiva Plotniece
Molbank 2022, 2022(3), M1402; https://doi.org/10.3390/M1402 - 6 Jul 2022
Viewed by 1634
Abstract
A synthesis of 3-(3,5-difluoro-3,5-bis((alkoxy)carbonyl)-2,6-dioxoheptan-4-yl)-1-methylpyridin-1-ium iodides with ethyl or nonyl ester groups at positions 3 and 5 was performed. Treatment of the corresponding 2’,6’-dimethyl-1’,4’-dihydro-[3,4’-bipyridine]-3’,5’-dicarboxylates with Selectfluor® followed by quaternization of pyridine moiety in the obtained dialkyl 2,4-diacetyl-2,4-difluoro-3-(pyridin-3-yl)pentanedioates with methyl iodide gave the desired [...] Read more.
A synthesis of 3-(3,5-difluoro-3,5-bis((alkoxy)carbonyl)-2,6-dioxoheptan-4-yl)-1-methylpyridin-1-ium iodides with ethyl or nonyl ester groups at positions 3 and 5 was performed. Treatment of the corresponding 2’,6’-dimethyl-1’,4’-dihydro-[3,4’-bipyridine]-3’,5’-dicarboxylates with Selectfluor® followed by quaternization of pyridine moiety in the obtained dialkyl 2,4-diacetyl-2,4-difluoro-3-(pyridin-3-yl)pentanedioates with methyl iodide gave the desired 3-(3,5-difluoro-3,5-bis((alkoxy)carbonyl)-2,6-dioxoheptan-4-yl)-1-methylpyridin-1-ium iodides. This type of compound would be useful as synthetic lipids for further development of the delivery systems. The obtained target compounds were fully characterized by 1H NMR, 19F NMR, 13C NMR, HRMS, IR and UV data. The estimation of self-assembling properties and characterization of the nanoparticles obtained by ethanol solution injection in an aqueous media were performed by dynamic light scattering (DLS) measurements. DLS measurement data showed that 3-(3,5-difluoro-3,5-bis((nonyloxy)carbonyl)-2,6-dioxoheptan-4-yl)-1-methylpyridin-1-ium iodide created liposomes with the average diameter of 300–400 nm and polydispersity index (PDI) value around 0.30–0.40, while 3-(3,5-difluoro-3,5-bis((ethyloxy)carbonyl)-2,6-dioxoheptan-4-yl)-1-methylpyridin-1-ium iodide formed a heterogeneous sample with PDI value 1, which was not prospective for delivery system development. Full article
Show Figures

Scheme 1

5 pages, 2334 KiB  
Communication
Styryl Hemicyanine Dye (E)-3-Methyl-2-(4-thiomorpholinostyryl)benzo[d]thiazol-3-ium Iodide for Nucleic Acids and Cell Nucleoli Visualization
by Aleksey A. Vasilev, Marina Miteva, Nikolay Ishkitiev, Maria Dragneva, Lora Topalova and Meglena I. Kandinska
Molbank 2022, 2022(2), M1392; https://doi.org/10.3390/M1392 - 20 Jun 2022
Cited by 3 | Viewed by 2189
Abstract
(E)-3-Methyl-2-(4-thiomorpholinostyryl)benzo[d]thiazol-3-ium iodide 1 was prepared by a convenient and reliable reaction procedure. The slight molar excess of the starting benzaldehyde and the mixture of ethanol: ethyl acetate in the ratio 3:1 as a solvent afforded a pure reaction product. The photophysical [...] Read more.
(E)-3-Methyl-2-(4-thiomorpholinostyryl)benzo[d]thiazol-3-ium iodide 1 was prepared by a convenient and reliable reaction procedure. The slight molar excess of the starting benzaldehyde and the mixture of ethanol: ethyl acetate in the ratio 3:1 as a solvent afforded a pure reaction product. The photophysical properties of the dye in a TE buffer in the absence and presence of double-stranded DNA (dsDNA) were elucidated. The low intrinsic fluorescence of 1 in TE buffer is followed by an increase in the fluorescence after dsDNA binding. The dye is nontoxic for stem cells from apical papilla and the most concentrated fluorescence is detected in the cell nucleoli. Full article
Show Figures

Graphical abstract

7 pages, 859 KiB  
Communication
Synthesis, Crystal Structure and Anti-Leukemic Activity of 1,3-Dihydro-1-{1-[4-(4-phenylpyrrolo[1,2-a]quinoxalin-3-yl)benzyl]piperidin-4-yl}-2H-benzimidazol-2-one
by Jean Guillon, Solène Savrimoutou, Sandra Albenque-Rubio, Noël Pinaud, Stéphane Moreau and Vanessa Desplat
Molbank 2022, 2022(1), M1333; https://doi.org/10.3390/M1333 - 9 Feb 2022
Cited by 4 | Viewed by 1963
Abstract
1,3-Dihydro-1-{1-[4-(4-phenylpyrrolo[1,2-a]quinoxalin-3-yl)benzyl]piperidin-4-yl}-2H-benzimidazol-2-one has been synthesized through a multi-step pathway starting from commercially available 2-nitroaniline. A structure characterization of this new substituted pyrrolo[1,2-a]quinoxaline compound was achieved by using FT-IR, 1H-NMR, 13C-NMR, X-Ray and HRMS spectral analysis. This [...] Read more.
1,3-Dihydro-1-{1-[4-(4-phenylpyrrolo[1,2-a]quinoxalin-3-yl)benzyl]piperidin-4-yl}-2H-benzimidazol-2-one has been synthesized through a multi-step pathway starting from commercially available 2-nitroaniline. A structure characterization of this new substituted pyrrolo[1,2-a]quinoxaline compound was achieved by using FT-IR, 1H-NMR, 13C-NMR, X-Ray and HRMS spectral analysis. This new pyrroloquinoxaline derivative shows an interesting cytotoxic potential against several human leukemia cell lines (HL60, K562 and U937 cells). Full article
Show Figures

Graphical abstract

2021

Jump to: 2024, 2023, 2022, 2020, 2019

7 pages, 2131 KiB  
Communication
CF3-Bis-TEMPO-Vis: New Visible Light Active Bis-Benzimidazolequinone Alkoxyamine
by Patrick Kielty, Pau Farràs, Dennis A. Smith and Fawaz Aldabbagh
Molbank 2021, 2021(4), M1300; https://doi.org/10.3390/M1300 - 26 Nov 2021
Viewed by 2199
Abstract
Alkoxyamines of TEMPO usually dissociate thermally at >100 °C; however, room temperature homolysis, activated by visible light, occurs with benzimidazolequinone derivatives. 1,1’-Dimethyl-2,2’-bis{[(2,2,6,6-tetramethylpiperidin-1-yl)oxy]methyl}-6-(trifluoromethyl)-1H,1’H-[5,5’-bibenzimidazole]-4,4’,7,7’-tetrone (CF3-Bis-TEMPO-Vis) is prepared in a 59% yield through NBS/H2SO4 oxidative [...] Read more.
Alkoxyamines of TEMPO usually dissociate thermally at >100 °C; however, room temperature homolysis, activated by visible light, occurs with benzimidazolequinone derivatives. 1,1’-Dimethyl-2,2’-bis{[(2,2,6,6-tetramethylpiperidin-1-yl)oxy]methyl}-6-(trifluoromethyl)-1H,1’H-[5,5’-bibenzimidazole]-4,4’,7,7’-tetrone (CF3-Bis-TEMPO-Vis) is prepared in a 59% yield through NBS/H2SO4 oxidative demethylations of the dimethoxybenzimidazole-benzimidazolequinone precursor with aqueous work up. The alternative basic work up in air gave the epoxide derivative of CF3-Bis-TEMPO-Vis. Unlike the latter CF3-epoxide, both alkoxyamine residues are labile under green light (470–600 nm), and the rate of TEMPO release is three times slower than Bis-TEMPO-Vis. Full article
Show Figures

Graphical abstract

5 pages, 542 KiB  
Communication
Regioselective Synthesis of 4-Bromo-3-formyl-N-phenyl-5-propylthiophene-2-carboxamide
by Sukanta Bar and Maxwell Israel Martin
Molbank 2021, 2021(4), M1296; https://doi.org/10.3390/M1296 - 16 Nov 2021
Cited by 1 | Viewed by 2158
Abstract
We synthesized 4-bromo-3-formyl-N-phenyl-5-propylthiophene-2-carboxamide by using three successive direct lithiations and a bromination reaction starting from thiophene. All these lithiation reactions were carried out at −78 °C to RT over a period of 1 to 24 h based on the reactivity of [...] Read more.
We synthesized 4-bromo-3-formyl-N-phenyl-5-propylthiophene-2-carboxamide by using three successive direct lithiations and a bromination reaction starting from thiophene. All these lithiation reactions were carried out at −78 °C to RT over a period of 1 to 24 h based on the reactivity of electrophile. This is a four-step protocol starting from thiophene with an overall yield of 47%. Full article
Show Figures

Graphical abstract

4 pages, 369 KiB  
Short Note
4,7-Bis(1,2,3,4,4a,9a-Hexahydro-9H-carbazol-9-yl)-[1,2,5]oxadiazolo[3,4-d]pyridazine
by Timofey N. Chmovzh, Karim S. Gaisin and Oleg A. Rakitin
Molbank 2021, 2021(4), M1295; https://doi.org/10.3390/M1295 - 5 Nov 2021
Cited by 2 | Viewed by 1906
Abstract
New donor-acceptor-donor (D-A-D)-type structures are widely used to design effective organic light-emitting diodes (OLEDs). In this communication, 4,7-bis(1,2,3,4,4a,9a-hexahydro-9H-carbazol-9-yl)-[1,2,5]oxadiazolo[3,4-d]pyridazine was obtained in a 65% yield by the treatment of 4,7-dichloro[1,2,5]oxadiazolo[3,4-d]pyridazine 1-oxide with 2,3,4,4a,9,9a-hexahydro-1H-carbazole. The structure of [...] Read more.
New donor-acceptor-donor (D-A-D)-type structures are widely used to design effective organic light-emitting diodes (OLEDs). In this communication, 4,7-bis(1,2,3,4,4a,9a-hexahydro-9H-carbazol-9-yl)-[1,2,5]oxadiazolo[3,4-d]pyridazine was obtained in a 65% yield by the treatment of 4,7-dichloro[1,2,5]oxadiazolo[3,4-d]pyridazine 1-oxide with 2,3,4,4a,9,9a-hexahydro-1H-carbazole. The structure of the newly synthesized compounds was established by means of an elemental analysis, 1H, 13C NMR, IR and UV spectroscopy, and HRMS and LR mass-spectrometry. Full article
Show Figures

Graphical abstract

5 pages, 560 KiB  
Short Note
6-(Chloromethyl)-N,1-dimethyl-1H-pyrazolo[3,4-d]pyrimidin-4-amine
by Vladimir A. Ogurtsov and Oleg A. Rakitin
Molbank 2021, 2021(4), M1294; https://doi.org/10.3390/M1294 - 1 Nov 2021
Cited by 1 | Viewed by 2040
Abstract
Functionally 4,6-disubstituted 1H-pyrazolo[3,4-d]pyrimidines are important compounds with various pharmacological activities. 1-Substituted 4-chloro-6-(chloromethyl)-1H-pyrazolo[3,4-d]pyrimidines are practically unexplored derivatives in this series. In this paper, it was shown that the nucleophilic substitution of 4-Chloro-6-(chloromethyl)-1-methyl-1H-pyrazolo[3,4-d]pyrimidine [...] Read more.
Functionally 4,6-disubstituted 1H-pyrazolo[3,4-d]pyrimidines are important compounds with various pharmacological activities. 1-Substituted 4-chloro-6-(chloromethyl)-1H-pyrazolo[3,4-d]pyrimidines are practically unexplored derivatives in this series. In this paper, it was shown that the nucleophilic substitution of 4-Chloro-6-(chloromethyl)-1-methyl-1H-pyrazolo[3,4-d]pyrimidine with methylamine produced selectively 4-substituted product, 6-(chloromethyl)-N,1-dimethyl-1H-pyrazolo[3,4-d]pyrimidin-4-amine. The structure of the synthesized compound was established by elemental analysis, high resolution mass-spectrometry, 1H, 13C-NMR, and IR spectroscopy, mass-spectrometry, and X-ray analysis. Full article
Show Figures

Graphical abstract

5 pages, 1293 KiB  
Communication
Ambient-Temperature Synthesis of (E)-N-(3-(tert-Butyl)-1-methyl-1H-pyrazol-5-yl)-1-(pyridin-2-yl)methanimine
by Diana Becerra, Justo Cobo and Juan-Carlos Castillo
Molbank 2021, 2021(3), M1250; https://doi.org/10.3390/M1250 - 7 Jul 2021
Cited by 1 | Viewed by 2095
Abstract
We report the ambient-temperature synthesis of novel (E)-N-(3-(tert-butyl)-1-methyl-1H-pyrazol-5-yl)-1-(pyridin-2-yl)methanamine 3 in 81% yield by a condensation reaction between 3-(tert-butyl)-1-methyl-1H-pyrazol-5-amine 1 and 2-pyridinecarboxaldehyde 2 in methanol using magnesium sulfate as a drying agent. [...] Read more.
We report the ambient-temperature synthesis of novel (E)-N-(3-(tert-butyl)-1-methyl-1H-pyrazol-5-yl)-1-(pyridin-2-yl)methanamine 3 in 81% yield by a condensation reaction between 3-(tert-butyl)-1-methyl-1H-pyrazol-5-amine 1 and 2-pyridinecarboxaldehyde 2 in methanol using magnesium sulfate as a drying agent. The N-pyrazolyl imine 3 was full characterized by IR, 1D, and 2D NMR spectroscopy, mass spectrometry, and elemental analysis. Full article
Show Figures

Figure 1

3 pages, 314 KiB  
Short Note
(2,3-Dihydro-1H-indol-5-ylmethyl)amine
by Vladimir A. Ogurtsov and Oleg A. Rakitin
Molbank 2021, 2021(3), M1248; https://doi.org/10.3390/M1248 - 5 Jul 2021
Viewed by 1986
Abstract
New (2,3-dihydro-1H-indol-5-ylmethyl)amine was synthesized from 2-((1-acetylindolin-5-yl)methyl)isoindoline-1,3-dione by simultaneous deprotection of phthalimide and acetyl groups. The structure of the newly synthesized compounds was established by elemental analysis, high resolution mass-spectrometry, 1H, 13C NMR and IR spectroscopy and mass-spectrometry. The resulting [...] Read more.
New (2,3-dihydro-1H-indol-5-ylmethyl)amine was synthesized from 2-((1-acetylindolin-5-yl)methyl)isoindoline-1,3-dione by simultaneous deprotection of phthalimide and acetyl groups. The structure of the newly synthesized compounds was established by elemental analysis, high resolution mass-spectrometry, 1H, 13C NMR and IR spectroscopy and mass-spectrometry. The resulting compound is a convenient intermediate for various disubstituted 1-(indolin-5-yl)methanamines, which may be of interest as substances with useful pharmacological properties. Full article
Show Figures

Graphical abstract

6 pages, 1287 KiB  
Short Note
(E)-4-Oxo-3,4-dihydroquinazoline-2-carbaldehyde Oxime
by Andreas S. Kalogirou, Andreas Kourtellaris and Panayiotis A. Koutentis
Molbank 2021, 2021(2), M1233; https://doi.org/10.3390/M1233 - 11 Jun 2021
Viewed by 2015
Abstract
Reaction of 4-oxo-3,4-dihydroquinazoline-2-carbaldehyde with hydroxylamine hydrochloride (1.1 equiv) in the presence of K2CO3 (1 equiv) gave (E)-4-oxo-3,4-dihydroquinazoline-2-carbaldehyde oxime (8) in 58% yield. The compound was fully characterized and the conformation of the oxime was supported by single crystal x-ray diffractometry. Full article
Show Figures

Graphical abstract

6 pages, 665 KiB  
Short Note
3-(tert-Butyl)-N-(4-methoxybenzyl)-1-methyl-1H-pyrazol-5-amine
by Diana Becerra, Hugo Rojas and Juan-Carlos Castillo
Molbank 2021, 2021(1), M1196; https://doi.org/10.3390/M1196 - 10 Mar 2021
Cited by 2 | Viewed by 2487
Abstract
We reported an efficient one-pot two-step synthesis of 3-(tert-butyl)-N-(4-methoxybenzyl)-1-methyl-1H-pyrazol-5-amine 3 in good yield by a solvent-free condensation/reduction reaction sequence starting from 3-(tert-butyl)-1-methyl-1H-pyrazol-5-amine 1 and p-methoxybenzaldehyde 2. The one-pot reductive amination proceeded [...] Read more.
We reported an efficient one-pot two-step synthesis of 3-(tert-butyl)-N-(4-methoxybenzyl)-1-methyl-1H-pyrazol-5-amine 3 in good yield by a solvent-free condensation/reduction reaction sequence starting from 3-(tert-butyl)-1-methyl-1H-pyrazol-5-amine 1 and p-methoxybenzaldehyde 2. The one-pot reductive amination proceeded by the formation in situ of the N-(5-pyrazolyl)imine 4 as key synthetic intermediate of other valuable pyrazole derivatives. This methodology is distinguished by its operational easiness, short reaction time, isolation and purification of the aldimine intermediate is not required. The structure of the synthesized N-heterocyclic amine 3 was fully characterized by FTIR-ATR, 1D and 2D NMR experiments, EIMS, and elemental analysis. Full article
Show Figures

Graphical abstract

10 pages, 2085 KiB  
Communication
Synthesis of 1,5-Disubstituted Tetrazoles in Aqueous Micelles at Room Temperature
by Mohammed Abdessalam, Madjid Ait Sidhoum, Fatima-Zohra Zradni and Hocine Ilikti
Molbank 2021, 2021(1), M1194; https://doi.org/10.3390/M1194 - 9 Mar 2021
Cited by 4 | Viewed by 2326
Abstract
The ongoing study is a Ugi-azide four-component reaction for the synthesis of 1,5-disubstituted tetrazole(1,5-DST), which involves an aldehyde, different amines, isocyanides, and as azide’s source the Trimethylsilylazide (TMSN3), in water as solvent using as catalyst the tetradecyltrimethylammonium bromide (TTAB) with a [...] Read more.
The ongoing study is a Ugi-azide four-component reaction for the synthesis of 1,5-disubstituted tetrazole(1,5-DST), which involves an aldehyde, different amines, isocyanides, and as azide’s source the Trimethylsilylazide (TMSN3), in water as solvent using as catalyst the tetradecyltrimethylammonium bromide (TTAB) with a load of (10% mole), which provides a hydrophobic micellar reaction site. This approach is a step toward a green chemistry reaction of 1,5 disubstituted tetrazole. A serie of 1, 5- disubstituted tetrazole was synthesized by engaging a large substrate scope, leading to yields between 43% and 56%, which are compared afterwards with those obtained with methanol as solvent. The results were confirmed by HRMS, IR, and 1D NMR experiments. Full article
Show Figures

Figure 1

7 pages, 1459 KiB  
Short Note
Ethyl 1-Butyl-2-(2-hydroxy-4-methoxyphenyl)-1H-benzo[d]imidazole-5-carboxylate
by Reshma Sathyanarayana and Boja Poojary
Molbank 2021, 2021(1), M1192; https://doi.org/10.3390/M1192 - 24 Feb 2021
Viewed by 2320
Abstract
Ethyl 4-(butylamino)-3-nitrobenzoate upon “one-pot” nitro-reductive cyclization using sodium dithionite and substituted aldehyde in dimethyl sulphoxide affords ethyl 1-butyl-2-(2-hydroxy-4-methoxyphenyl)-1H-benzo[d]imidazole-5-carboxylate in an 87% yield. The structural characterization was determined by Fourier-transfer infrared spectroscopy (FT-IR), Proton nuclear magnetic resonance (1H-NMR), [...] Read more.
Ethyl 4-(butylamino)-3-nitrobenzoate upon “one-pot” nitro-reductive cyclization using sodium dithionite and substituted aldehyde in dimethyl sulphoxide affords ethyl 1-butyl-2-(2-hydroxy-4-methoxyphenyl)-1H-benzo[d]imidazole-5-carboxylate in an 87% yield. The structural characterization was determined by Fourier-transfer infrared spectroscopy (FT-IR), Proton nuclear magnetic resonance (1H-NMR), Carbon-13 nuclear magnetic resonance (13C-NMR), mass spectrometry, Ultraviolet-visible(UV-Vis), photoluminescence (PL), thin-film solid emission spectra, cyclic voltammetry (CV) and thermogravimetric (TGA) analysis. Molecular electrostatic potential (MEP) was studied to determine the reactive sites of the molecule. Full article
Show Figures

Figure 1

5 pages, 907 KiB  
Short Note
2-Amino-5-chloro-1H-pyrrole-3,4-dicarbonitrile
by Andreas S. Kalogirou and Panayiotis A. Koutentis
Molbank 2021, 2021(1), M1191; https://doi.org/10.3390/M1191 - 13 Feb 2021
Cited by 1 | Viewed by 2662
Abstract
The reaction of tetracyanoethylene (TCNE) with HCl (g) in the presence of Sn (1 equiv) and AcOH resulted in 2-amino-5-chloro-1H-pyrrole-3,4-dicarbonitrile in a 74% yield. The compound was fully characterized. Full article
Show Figures

Graphical abstract

7 pages, 1489 KiB  
Communication
Tetramethyl 1,1′-(2-[{4,5-bis(Methoxycarbonyl)-1H-1,2,3-triazol-1-yl}methyl]-2-[(4-methylphenyl)sulfonamido]propane-1,3-diyl)bis(1H-1,2,3-triazole-4,5-dicarboxylate)
by Serigne Abdou Khadir Fall, Sara Hajib, Oumaima Karai, Younas Aouine, Salaheddine Boukhssas, Hassane Faraj and Anouar Alami
Molbank 2021, 2021(1), M1186; https://doi.org/10.3390/M1186 - 31 Jan 2021
Cited by 1 | Viewed by 2216
Abstract
A new compound tetramethyl 1,1′-(2-[{4,5-bis(methoxycarbonyl)-1H-1,2,3-triazol-1-yl}methyl]-2-[(4-methylphenyl)sulfonamido]propane-1,3-diyl)bis(1H-1,2,3-triazole-4,5-dicarboxylate) (3) was prepared in two steps starting from 2-((4-methylphenyl)sulfonamido)-2-((tosyloxy)methyl)propane-1,3-diylbis(4-methylbenzenesulfonate) (1), with an overall yield of 74%. The key step being the copper-free Huisgen cycloaddition between N [...] Read more.
A new compound tetramethyl 1,1′-(2-[{4,5-bis(methoxycarbonyl)-1H-1,2,3-triazol-1-yl}methyl]-2-[(4-methylphenyl)sulfonamido]propane-1,3-diyl)bis(1H-1,2,3-triazole-4,5-dicarboxylate) (3) was prepared in two steps starting from 2-((4-methylphenyl)sulfonamido)-2-((tosyloxy)methyl)propane-1,3-diylbis(4-methylbenzenesulfonate) (1), with an overall yield of 74%. The key step being the copper-free Huisgen cycloaddition between N-(1,3-diazido-2-(azidomethyl)propan-2-yl)-4-methylbenzenesulfonamide (2) and commercially available dimethyl acetylenedicarboxylate. The chemical structure of compound 3 was determined by IR, 1D and 2D NMR experiments, and elemental analysis. Full article
Show Figures

Graphical abstract

6 pages, 714 KiB  
Short Note
N-(6-Chloro-3-nitropyridin-2-yl)-5-(1-methyl-1H-pyrazol-4-yl)isoquinolin-3-amine
by Valentin Wydra, Stefan Gerstenecker, Dieter Schollmeyer, Stanislav Andreev, Teodor Dimitrov, Ricardo Augusto Massarico Serafim, Stefan Laufer and Matthias Gehringer
Molbank 2021, 2021(1), M1181; https://doi.org/10.3390/M1181 - 18 Jan 2021
Cited by 2 | Viewed by 3244
Abstract
Here we describe the synthesis of N-(6-chloro-3-nitropyridin-2-yl)5-(1-methyl-1H-pyrazol-4-yl)isoquinolin-3-amine via a three-step procedure including a Buchwald–Hartwig arylamination with benzophenone imine and a highly regioselective nucleophilic aromatic substitution. The title compound was analyzed by nuclear magnetic resonance spectroscopy (1H, 13C, [...] Read more.
Here we describe the synthesis of N-(6-chloro-3-nitropyridin-2-yl)5-(1-methyl-1H-pyrazol-4-yl)isoquinolin-3-amine via a three-step procedure including a Buchwald–Hartwig arylamination with benzophenone imine and a highly regioselective nucleophilic aromatic substitution. The title compound was analyzed by nuclear magnetic resonance spectroscopy (1H, 13C, HSQC, HMBC, COSY, DEPT90 and NOESY), high resolution mass spectrometry (ESI-TOF-HRMS) and infrared spectroscopy (ATR-IR) and its structure was confirmed by single crystal X-ray diffraction. The inhibitory potency of the title compound was evaluated for selected kinases harboring a rare cysteine in the hinge region (MPS1, MAPKAPK2 and p70S6Kβ/S6K2). Full article
Show Figures

Figure 1

4 pages, 1891 KiB  
Short Note
(S)-1-(Ethoxycarbonyl)ethyl(2R,5S)-2,5-dimethyl-1,3-dioxolan-4-one-2-carboxylate
by R. Alan Aitken, Oliver E. Haslett and Alexandra M. Z. Slawin
Molbank 2021, 2021(1), M1178; https://doi.org/10.3390/M1178 - 2 Jan 2021
Cited by 1 | Viewed by 2076
Abstract
The title compound was obtained in low yield in the condensation of ethyl pyruvate and lactic acid. Its structure is determined by NMR methods and x-ray diffraction and the mechanism for formation of this 1:2 adduct from the initial 1:1 adduct is considered. [...] Read more.
The title compound was obtained in low yield in the condensation of ethyl pyruvate and lactic acid. Its structure is determined by NMR methods and x-ray diffraction and the mechanism for formation of this 1:2 adduct from the initial 1:1 adduct is considered. Full article
Show Figures

Figure 1

2020

Jump to: 2024, 2023, 2022, 2021, 2019

4 pages, 370 KiB  
Short Note
Methyl (2E)-3-[3-Benzyl-2-(3-methoxy-3-oxoprop-1-yn-1-yl)-2-(1-naphthyl)imidazolidin-1-yl]acrylate
by Alexandra S. Golubenkova, Nikita E. Golantsov and Leonid G. Voskressensky
Molbank 2021, 2021(1), M1176; https://doi.org/10.3390/M1176 - 30 Dec 2020
Viewed by 2118
Abstract
Compounds with propargylamine moiety are useful synthetic precursors of several important classes of nitrogen-containing heterocycles. The title compound, methyl (2E)-3-[3-benzyl-2-(3-methoxy-3-oxoprop-1-yn-1-yl)-2-(1-naphthyl)imidazolidine-1-yl]acrylate, has been prepared by domino-reaction, employing easily available 1-benzyl-2-(1-naphthyl)-4,5-dihydro-1H-imidazole and methyl propiolate in a high 92% yield. The structure [...] Read more.
Compounds with propargylamine moiety are useful synthetic precursors of several important classes of nitrogen-containing heterocycles. The title compound, methyl (2E)-3-[3-benzyl-2-(3-methoxy-3-oxoprop-1-yn-1-yl)-2-(1-naphthyl)imidazolidine-1-yl]acrylate, has been prepared by domino-reaction, employing easily available 1-benzyl-2-(1-naphthyl)-4,5-dihydro-1H-imidazole and methyl propiolate in a high 92% yield. The structure of title compound was determined using 1H-NMR, 13C-NMR, UV, FT-IR and HRMS (High-Resolution Mass Spectrometry). Full article
Show Figures

Scheme 1

4 pages, 1659 KiB  
Short Note
4,4′-(Pyrrolo[3,2-b]pyrrole-1,4-diyl)dianiline
by Lorenza Giordano, Rafael Ballesteros and Rafael Ballesteros-Garrido
Molbank 2020, 2020(4), M1169; https://doi.org/10.3390/M1169 - 23 Nov 2020
Cited by 2 | Viewed by 2194
Abstract
4,4′-(Pyrrolo[3,2-b]pyrrole-1,4-diyl)dianiline was synthesized in one step from benzene-1,4-diamine and ethylene glycol with Pd/Al2O3 and ZnO. The title compound was characterized by means of NMR techniques and HRMS mass spectrometry. Full article
Show Figures

Scheme 1

7 pages, 484 KiB  
Short Note
6-Nitro-7-tosylquinazolin-4(3H)-one
by Thi Ngoc Nguyen, Thi Phuong Thuy Tran, Thi Hoang Mai Vu, Hoa Binh Nguyen, Nguyet Suong Huyen Dao, Van Giang Nguyen, Dinh Luyen Nguyen, Nguyen Trieu Trinh and Van Hai Nguyen
Molbank 2020, 2020(4), M1168; https://doi.org/10.3390/M1168 - 21 Nov 2020
Viewed by 2764
Abstract
Sulfones are important building blocks in the construction of biologically active molecules or functional materials. The sulfonyl functional group in sulfones is so versatile that it can act as either a nucleophile, an electrophile, or a radical in different organic reactions. Recently, quinazoline [...] Read more.
Sulfones are important building blocks in the construction of biologically active molecules or functional materials. The sulfonyl functional group in sulfones is so versatile that it can act as either a nucleophile, an electrophile, or a radical in different organic reactions. Recently, quinazoline sulfones have been used to build asymmetrical ether derivatives as inhibitors of signaling pathways governed by tyrosine kinases and the epidermal growth factor-receptor. In this paper, we report a facile synthesis of a novel quinazoline sulfone, 6-nitro-7-tosylquinazolin-4(3H)-one (III), using the modified protocol from 7-chloro-6-nitroquinazolin-4(3H)-one (I) and sodium p-toluenesulfinate (II). The structure of the title compound III was determined using mass-spectrometry, FT-IR, 1H-NMR, 13C-NMR, DEPT, HSQC (Heteronuclear single quantum coherence), HMBC (Heteronuclear Multiple Bond Correlation Spectroscopy) spectroscopies, and PXRD analysis. Full article
Show Figures

Graphical abstract

5 pages, 745 KiB  
Short Note
Ethyl (S)-2-Benzamido-5-[(4,6-dimethylpyrimidin-2-yl)amino]pentanoate
by Mario A. Leyva-Acuña, Francisco Delgado-Vargas, Gabriela López-Angulo and Julio Montes-Avila
Molbank 2020, 2020(4), M1166; https://doi.org/10.3390/M1166 - 13 Nov 2020
Viewed by 2327
Abstract
Pyrimidines are compounds with a wide range of biological activities, and the synthesis of pyrimidine derivatives—useful in chemical and medicinal applications—is important in medicinal chemistry. This work shows the synthesis under microwave irradiation of the novel compound ethyl (S)-2-benzamido-5-[(4,6-dimethylpyrimidin-2-yl)amino]pentanoate (3 [...] Read more.
Pyrimidines are compounds with a wide range of biological activities, and the synthesis of pyrimidine derivatives—useful in chemical and medicinal applications—is important in medicinal chemistry. This work shows the synthesis under microwave irradiation of the novel compound ethyl (S)-2-benzamido-5-[(4,6-dimethylpyrimidin-2-yl)amino]pentanoate (3) from (S)-N-α-benzoyl-l-arginine ethyl ester hydrochloride (1) and acetylacetone (2). Compound 3 was easily purified, obtained in moderate yield (70%), and fully characterized by UV-Vis, FTIR-ATR spectroscopy, 1H-NMR, 13C-NMR, HRMS, and EI-MS. Full article
Show Figures

Scheme 1

5 pages, 334 KiB  
Short Note
Sodium N-(3,5-Bis(ethoxycarbonyl)-2,6-dimethyl-1,4-dihydropyridine-4-carbonyl)-l-methioninate
by Egils Bisenieks, Janis Poikans, Aiva Plotniece, Eiva Bernotiene, Wei-Bor Tsai and Arkadij Sobolev
Molbank 2020, 2020(3), M1148; https://doi.org/10.3390/M1148 - 14 Jul 2020
Viewed by 2817
Abstract
The development of the methods for amide bond formation is important for various uses in the laboratory and industrial applications. The compounds combined in their structures 1,4-dihydroisonicotinic acids and amino acids linked with an amide bond can be considered as “privileged structures” due [...] Read more.
The development of the methods for amide bond formation is important for various uses in the laboratory and industrial applications. The compounds combined in their structures 1,4-dihydroisonicotinic acids and amino acids linked with an amide bond can be considered as “privileged structures” due to their broad range of biological activities. Herein, the formation of amide bond between 1,4-dihydroisonicotinic acid and l-methionine is reported. The coupling of l-methionine with pentafluorophenyl active ester of 1,4-dihydroisonicotinic acid appears to be a convenient and effective method for amide bond formation. Sodium N-(3,5-bis(ethoxycarbonyl)-2,6-dimethyl-1,4-dihydropyridine-4-carbonyl)-l-methioninate has been successfully synthesized via a procedure where the key step is amide formation from 5-diethyl 4-(perfluorophenyl) 2,6-dimethyl-1,4-dihydropyridine-3,4,5-tricarboxylate and l-methionine. Sodium salt formation was performed to improve physicochemical properties, such as solubility of the l-methionine-derived 1,4-dihydroisonicotinamide. The obtained target compound was fully characterized by UV, IR, 1H NMR, 13C NMR, MS, and microanalysis. Full article
Show Figures

Graphical abstract

5 pages, 586 KiB  
Short Note
(2S,3R,6R)-2-[(R)-1-Hydroxyallyl]-4,4-dimethoxy-6-methyltetrahydro-2H-pyran-3-ol
by Jack Bennett and Paul V. Murphy
Molbank 2020, 2020(2), M1140; https://doi.org/10.3390/M1140 - 3 Jun 2020
Viewed by 2406
Abstract
(2S,3R,6R)-2-[(R)-1-Hydroxyallyl]-4,4-dimethoxy-6-methyltetrahydro-2H-pyran-3-ol was isolated in 18% after treating the glucose derived (5R,6S,7R)-5,6,7-tris[(triethylsilyl)oxy]nona-1,8-dien-4-one with (1S)-(+)-10-camphorsulfonic acid (CSA). The one-pot formation of the title compound involved triethylsilyl (TES) [...] Read more.
(2S,3R,6R)-2-[(R)-1-Hydroxyallyl]-4,4-dimethoxy-6-methyltetrahydro-2H-pyran-3-ol was isolated in 18% after treating the glucose derived (5R,6S,7R)-5,6,7-tris[(triethylsilyl)oxy]nona-1,8-dien-4-one with (1S)-(+)-10-camphorsulfonic acid (CSA). The one-pot formation of the title compound involved triethylsilyl (TES) removal, alkene isomerization, intramolecular conjugate addition and ketal formation. The compound was characterized by 1H and 13C NMR spectroscopy, ESI mass spectrometry and IR spectroscopy. NMR spectroscopy was used to establish the product structure, including the conformation of its tetrahydropyran ring. Full article
Show Figures

Scheme 1

6 pages, 887 KiB  
Communication
Synthesis of (R) and (S)-3-Chloro-5-(2,4-dimethylpiperazin-1-yl)-4H-1,2,6-thiadiazin-4-ones
by Andreas S. Kalogirou, Christopher R. M. Asquith and Panayiotis A. Koutentis
Molbank 2020, 2020(2), M1139; https://doi.org/10.3390/M1139 - 1 Jun 2020
Cited by 2 | Viewed by 2484
Abstract
The reaction of 3,5-dichloro-4H-1,2,6-thiadiazin-4-one with (R) and (S)-1,3-dimethylpiperazines (1 equiv), in THF, at ca. 20 °C gives (R) and (S)-3-chloro-5-(2,4-dimethylpiperazin-1-yl)-4H-1,2,6-thiadiazin-4-ones in 70% and 68% yields, respectively. The new compounds were fully characterized. Full article
Show Figures

Figure 1

4 pages, 518 KiB  
Short Note
Methyl 2-(1-methyl-3-oxoisoindolin-1-yl)acetate
by Antonia Di Mola, Antonio Macchia, Laura Palombi and Antonio Massa
Molbank 2020, 2020(2), M1131; https://doi.org/10.3390/M1131 - 8 May 2020
Cited by 1 | Viewed by 2369
Abstract
In this work, we report a facile access to a 3,3-disubstituted isoindolinone by means of Krapcho decarboxylation reaction of the respective substituted dimethyl malonate derivative. Good isolated yields were obtained under mild reaction conditions. Full article
Show Figures

Graphical abstract

5 pages, 1270 KiB  
Short Note
2-(Fluoromethyl)-4,7-dimethoxy-1-methyl-1H-benzimidazole
by Patrick Kielty, Pau Farràs, Dennis A. Smith and Fawaz Aldabbagh
Molbank 2020, 2020(2), M1129; https://doi.org/10.3390/M1129 - 1 May 2020
Cited by 2 | Viewed by 3119
Abstract
Selectfluor (1-chloromethyl-4-fluoro-1,4-diazoniabicyclo[2.2.2]octane bis(tetrafluoroborate)) substitutes the TEMPO free radical with fluorine on 4,7-dimethoxy-1-methyl-2-{[(2,2,6,6-tetramethylpiperidin-1-yl)oxy]methyl}-1H-benzimidazole to give the title compound in a 77% yield. A mechanism is proposed for the formation of this novel methylene fluoride. Full article
Show Figures

Graphical abstract

6 pages, 841 KiB  
Communication
Synthesis of (R) and (S)-3-Chloro-5-(3-methylmorpholino)-4H-1,2,6-thiadiazin-4-ones
by Andreas S. Kalogirou, Christopher R. M. Asquith and Panayiotis A. Koutentis
Molbank 2020, 2020(2), M1128; https://doi.org/10.3390/M1128 - 27 Apr 2020
Cited by 1 | Viewed by 2341
Abstract
Reaction of 3,5-dichloro-4H-1,2,6-thiadiazin-4-one with (R) and (S)-3-methylmorpholines (2 equiv), in THF, at ca. 20 °C gave (R) and (S)-3-chloro-5-(3-methylmorpholino)-4H-1,2,6-thiadiazin-4-ones in 95 and 97% yields, respectively. The new compounds were fully characterized. Full article
Show Figures

Graphical abstract

7 pages, 2065 KiB  
Short Note
2,6-exo-8,12-exo-10-Butyl-13-oxa-3,5-dithia-10-azatetracyclo[5.5.1.02,6.08,12]tridecane-9,11-dione
by R. Alan Aitken, Fiona M. Fotherby and Alexandra M. Z. Slawin
Molbank 2020, 2020(2), M1123; https://doi.org/10.3390/M1123 - 2 Apr 2020
Cited by 2 | Viewed by 2682
Abstract
The title compound was obtained in low yield and spectroscopically characterised. Its X-ray structure was compared with the X-ray structures of other crystallographically-characterised 2-unsubstituted 1,3-dithiolanes. Full article
Show Figures

Graphical abstract

5 pages, 727 KiB  
Communication
6-Imino-1,2,3,4,8,9,10,11-octahydropyrido[1,2-a]pyrido[1′,2′:1,2]imidazo[4,5-f]benzimidazole-13-one: Synthesis and Cytotoxicity Evaluation
by Darren Conboy and Fawaz Aldabbagh
Molbank 2020, 2020(1), M1118; https://doi.org/10.3390/M1118 - 5 Mar 2020
Cited by 4 | Viewed by 2521
Abstract
The first report of an iminoquinone of imidazo[4,5-f]benzimidazole is described. The 2D-NOESY spectrum of 1,2,3,4,8,9,10,11-octahydropyrido[1,2-a]pyrido[1’,2’:1,2]imidazo[4,5-f]benzimidazol-6-amine was used to confirm the location of the imine moiety at the C-6 position of the title compound. Cytotoxicity data from the National Cancer Institute are included. Full article
Show Figures

Figure 1

6 pages, 1515 KiB  
Short Note
Diethyl pyrrole-2,5-dicarboxylate
by R. Alan Aitken, Charles Bloomfield, Liam J. R. McGeachie and Alexandra M. Z. Slawin
Molbank 2020, 2020(1), M1117; https://doi.org/10.3390/M1117 - 17 Feb 2020
Cited by 1 | Viewed by 2391
Abstract
The title compound was obtained in moderate yield by a new and unexpected base-induced ring contraction from a 1,4-thiazine precursor. Its X-ray structure showing hydrogen bonded dimers was compared with those of other crystallographically characterised 2-acylpyrroles. Full article
Show Figures

Figure 1

7 pages, 1201 KiB  
Communication
1-Phenyl-8-[[4-(pyrrolo[1,2-a]quinoxalin-4-yl)phenyl]methyl]-1,3,8-triazaspiro[4.5]decan-4-one: Synthesis, Crystal Structure and Anti-Leukemic Activity
by Jean Guillon, Solène Savrimoutou, Sandra Rubio, Stéphane Moreau, Noël Pinaud, Mathieu Marchivie and Vanessa Desplat
Molbank 2020, 2020(1), M1113; https://doi.org/10.3390/M1113 - 29 Jan 2020
Cited by 7 | Viewed by 2544
Abstract
1-Phenyl-8-[[4-(pyrrolo[1,2-a]quinoxalin-4-yl)phenyl]methyl]-1,3,8-triazaspiro[4.5]decan-4-one has been successfully synthesized via a multi-step pathway starting from 2-nitroaniline. Structure characterization of this original pyrrolo[1,2-a]quinoxaline derivative was achieved by FT-IR, 1H-NMR, 13C-NMR, X-Ray and HRMS spectral analysis. This title compound shows interesting cytotoxic potential [...] Read more.
1-Phenyl-8-[[4-(pyrrolo[1,2-a]quinoxalin-4-yl)phenyl]methyl]-1,3,8-triazaspiro[4.5]decan-4-one has been successfully synthesized via a multi-step pathway starting from 2-nitroaniline. Structure characterization of this original pyrrolo[1,2-a]quinoxaline derivative was achieved by FT-IR, 1H-NMR, 13C-NMR, X-Ray and HRMS spectral analysis. This title compound shows interesting cytotoxic potential against several human leukemia cell lines (K562, HL60, and U937 cells). Full article
Show Figures

Graphical abstract

2019

Jump to: 2024, 2023, 2022, 2021, 2020

9 pages, 2505 KiB  
Communication
Novel One-Pot Synthesis of Methyl 4-Hydroxy-2-thioxo-1,2-dihydroquinoline-3-carboxylate: Synthetic and Crystallographic Studies
by Sergiy M. Kovalenko, Oleksandr G. Drushlyak, Irina S. Konovalova, Illia O. Mariutsa, Dmitry V. Kravchenko, Alexandre V. Ivachtchenko and Oleg D. Mitkin
Molbank 2019, 2019(4), M1085; https://doi.org/10.3390/M1085 - 14 Oct 2019
Cited by 2 | Viewed by 2589
Abstract
A new suitable method of synthesis of methyl 4-hydroxy-2-thioxo-1,2-dihydroquinoline-3-carboxylate by condensation of methyl 2-isothiocyanatobenzoate and methyl malonate is described. The structure of the compound both and by-product methyl 2-(methoxycarbonothioylamino)benzoate was confirmed by means of elemental analysis, 1H NMR, 13C NMR, LC/MS [...] Read more.
A new suitable method of synthesis of methyl 4-hydroxy-2-thioxo-1,2-dihydroquinoline-3-carboxylate by condensation of methyl 2-isothiocyanatobenzoate and methyl malonate is described. The structure of the compound both and by-product methyl 2-(methoxycarbonothioylamino)benzoate was confirmed by means of elemental analysis, 1H NMR, 13C NMR, LC/MS and single crystal X-ray diffraction. UV/Vis and IR spectra of compounds are described. The presence of a strong intramolecular hydrogen bond between the hydroxy group and the carbonyl oxygen atom of the ester group in methyl 4-hydroxy-2-thioxo-1,2-dihydroquinoline-3-carboxylate is shown. The crystal structure of product was stabilized through intermolecular hydrogen bonds. Full article
Show Figures

Graphical abstract

8 pages, 1490 KiB  
Short Note
3-{[(2,3-Dichlorophenyl)amino]methyl}-5-(furan-2-ylmethylidene)-1,3-thiazolidine-2,4-dione
by Nadine Uwabagira and Balladka Kunhana Sarojini
Molbank 2019, 2019(4), M1083; https://doi.org/10.3390/M1083 - 3 Oct 2019
Cited by 1 | Viewed by 2219
Abstract
The compound 3-{[(2,3-Dichlorophenyl)amino]methyl}-5-(furan-2-ylmethylidene)-1,3-thiazolidine-2,4-dione has been designed, synthesized, and screened for its in vitro antibreast cancer activity, using human breast adenocarcinoma cell lines (MCF-7) and in vitro anti-inflammatory activity. By hemolysis assay, it showed that it has a nonhemolytic and nontoxic effect on human [...] Read more.
The compound 3-{[(2,3-Dichlorophenyl)amino]methyl}-5-(furan-2-ylmethylidene)-1,3-thiazolidine-2,4-dione has been designed, synthesized, and screened for its in vitro antibreast cancer activity, using human breast adenocarcinoma cell lines (MCF-7) and in vitro anti-inflammatory activity. By hemolysis assay, it showed that it has a nonhemolytic and nontoxic effect on human blood cell. The title compound 5, subjected to in vitro activities, showed that it is cytotoxic with an IC50 of 42.30 µM and a good anti-inflammatory agent. The docking results against cyclin dependent kinase 2 (CDK2) (PDB ID: 3QQK) gave insights on its inhibitory activity. Full article
Show Figures

Figure 1

5 pages, 1523 KiB  
Short Note
4-[(3,5-Dimethyl-1H-pyrazol-1-yl)methyl]-4-methyl-2-phenyl-4,5-dihydrooxazole
by Sara Hajib, Anouar Alami, Hassane Faraj and Younas Aouine
Molbank 2019, 2019(3), M1074; https://doi.org/10.3390/M1074 - 19 Jul 2019
Cited by 2 | Viewed by 2715
Abstract
The compound, 4-[(3,5-dimethyl-1H-pyrazol-1-yl)methyl]-4-methyl-2-phenyl-4,5-dihydrooxazole 2 was prepared in high yield, through nucleophilic substitution reaction of the O-tosyl oxazoline derivative 1, by heating in dimethyl sulfoxide (DMSO) and in presence of KOH as base. The structure of the synthesized compound was [...] Read more.
The compound, 4-[(3,5-dimethyl-1H-pyrazol-1-yl)methyl]-4-methyl-2-phenyl-4,5-dihydrooxazole 2 was prepared in high yield, through nucleophilic substitution reaction of the O-tosyl oxazoline derivative 1, by heating in dimethyl sulfoxide (DMSO) and in presence of KOH as base. The structure of the synthesized compound was established on the basis of NMR spectroscopy (1H, 13C), MS data and elemental analysis. Full article
Show Figures

Figure 1

Back to TopTop