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Molbank
Volume 2023
Issue 4
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Molbank, Volume 2023, Issue 4 (December 2023) – 20 articles

Cover Story (view full-size image): Although the triethylammonium betaine of squaric acid was first reported almost 30 years ago, its structure has remained unpublished until now. The crystal structure determination via the use of Hirshfeld atom refinement reveals that the compound is best described as a resonance hybrid structure with a partial enolate character of the two lateral squaric acid C=O groups. The solid-state supramolecular structure features weak intermolecular C–H···O hydrogen bonds. The present study provides the first structural characterization of a betaine of squaric acid containing a four-coordinate nitrogen atom directly attached to the four-membered ring. View this paper
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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 1284
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
(This article belongs to the Collection Heterocycle Reactions)
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9 pages, 1120 KiB  
Short Note
4-(5-Benzyl-3-((4-fluorophenyl)sulfonyl)-5-methyl-4,5-dihydrofuran-2-yl)-2-nitrobenzamide
by Oscar Leonardo Avendaño Leon, Christophe Curti, Hussein El-Kashef, Youssef Kabri, Sébastien Redon and Patrice Vanelle
Molbank 2023, 2023(4), M1750; https://doi.org/10.3390/M1750 - 15 Dec 2023
Viewed by 1168
Abstract
As part of our ongoing attempt to broaden the applications of the amidoxime moiety as a potential source of new antileishmanial agents, this study focuses on the product 4-(5-Benzyl-3-((4-fluorophenyl)sulfonyl)-5-methyl-4,5-dihydrofuran-2-yl)-2-nitrobenzamide. This unexpected amide was obtained in an 85% yield as the major product with [...] Read more.
As part of our ongoing attempt to broaden the applications of the amidoxime moiety as a potential source of new antileishmanial agents, this study focuses on the product 4-(5-Benzyl-3-((4-fluorophenyl)sulfonyl)-5-methyl-4,5-dihydrofuran-2-yl)-2-nitrobenzamide. This unexpected amide was obtained in an 85% yield as the major product with a conventional amidoxime synthesis protocol (Ethanol/Na2CO3) involving the reaction of hydroxylamine and a nitrile group. The formation of this amide derivative instead of the expected amidoxime can be attributed to two complementary effects: the strong electron effect of the nitro group and the influence of ethanol, a polar protic solvent. Alternatively, the desired amidoxime derivative, 4-(5-benzyl-3-((4-fluorophenyl)sulfonyl)-5-methyl-4,5-dihydrofuran-2-yl)-N′-hydroxy-2-nitrobenzimidamide, was obtained in an 80% yield by an alternative protocol (DMSO/KOtBu). This original compound, featuring a nitro group in the ortho position to the amidoxime, will be further evaluated, both in the field of medicinal chemistry and in other relevant areas, highlighting an unusual method to access amidoximes from hindered substrates. Full article
(This article belongs to the Collection Molecules from Side Reactions)
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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 1179
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
(This article belongs to the Collection Heterocycle Reactions)
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11 pages, 3280 KiB  
Communication
Building Triazolated Macrocycles from Bis-Propargylated Calix[4]arenes and Bis-Azidomethylated Azobenzene or Stilbene
by Ivan Lentin, Ilia Korniltsev, Alexander Gorbunov, Dmitry Cheshkov, Stanislav Bezzubov, Vladimir Kovalev and Ivan Vatsouro
Molbank 2023, 2023(4), M1748; https://doi.org/10.3390/M1748 - 07 Dec 2023
Viewed by 1371
Abstract
Copper(I)-catalyzed azide-alkyne cycloaddition was employed to construct biscalixarene assemblies from the calix[4]arene dipropargyl ethers and 4,4′-bis-azidomethylated azobenzene or stilbene. Three bis(calixarenes) having the calix[4]arene cores linked to each other by pairs of (E)-azobenzene/stilbene units through four triazole groups were obtained as [...] Read more.
Copper(I)-catalyzed azide-alkyne cycloaddition was employed to construct biscalixarene assemblies from the calix[4]arene dipropargyl ethers and 4,4′-bis-azidomethylated azobenzene or stilbene. Three bis(calixarenes) having the calix[4]arene cores linked to each other by pairs of (E)-azobenzene/stilbene units through four triazole groups were obtained as confirmed by NMR, HRMS and X-ray diffraction data. Nevertheless, the formation of larger macrocycles and polymeric/oligomeric products was found to be the major competing process that seriously limited the applicability of the one-step macrocyclization approach for the construction of photoresponsive biscalixarene assemblies linked by pairs of azobenzene/stilbene units. Full article
(This article belongs to the Section Organic Synthesis)
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12 pages, 1961 KiB  
Communication
5,8-Quinolinedione Attached to Quinone Derivatives: XRD Diffraction, Fourier Transform Infrared Spectra and Computational Analysis
by Arkadiusz Sokal, Roman Wrzalik, Joanna Klimontko, Elwira Chrobak, Ewa Bębenek and Monika Kadela-Tomanek
Molbank 2023, 2023(4), M1747; https://doi.org/10.3390/M1747 - 28 Nov 2023
Viewed by 1117
Abstract
Quinoline and isoquinoline moieties occur in many natural and synthetic compounds exhibiting high biological activity. The purpose of this study was to analyze the chemical structures of 5,8-quinolinedione and 5,8-isoquinoline derivatives using FT-IR spectroscopy supplemented with theoretical DFT calculations. Spectroscopic measurements were conducted [...] Read more.
Quinoline and isoquinoline moieties occur in many natural and synthetic compounds exhibiting high biological activity. The purpose of this study was to analyze the chemical structures of 5,8-quinolinedione and 5,8-isoquinoline derivatives using FT-IR spectroscopy supplemented with theoretical DFT calculations. Spectroscopic measurements were conducted using the attenuated total reflection (ATR) mode in the frequency range of 4000–400 cm−1. An analysis of FT-IR spectra was carried out, assigning the characteristic vibration frequencies of various functional groups to individual peaks. It was found that the experimental and calculated FT-IR spectra showed a good correlation for all the compounds under study. The most significant difference in the spectra occurred in the region of carbonyl bands. For compounds with the 5,8-quinolinedione moiety, two separated C=O vibration peaks were observed, while for compounds with the 5,8-isoquinolinedione moiety, the carbonyl vibrations created only one peak. This difference makes it possible to distinguish between the 5,8-quinolinedione and 5,8-isoquinolinedione derivatives. Full article
(This article belongs to the Section Structure Determination)
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6 pages, 1559 KiB  
Short Note
2-(4-(Fluorosulfonyloxy)phenyl)benzoxazole
by Nadezhda V. Danilenko, Mariia O. Lutsuk, Svetlana E. Patlasova, Elena I. Korotkova and Andrei I. Khlebnikov
Molbank 2023, 2023(4), M1746; https://doi.org/10.3390/M1746 - 27 Nov 2023
Viewed by 1135
Abstract
New 2-(4-(fluorosulfonyloxy)phenyl)benzoxazole (2) was synthesized through the SuFEx click reaction in a two-chamber reactor. The effect of silylation on the yield of the target compound was investigated. The fluorescent properties of compound 2 were determined using experimental and computational methods. Full article
(This article belongs to the Section Organic Synthesis)
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7 pages, 627 KiB  
Communication
Synthesis and In Silico Drug-Likeness Modeling of 5-FU/ASA Hybrids
by Wilson Castrillón-López, Andrés F. Yepes and Wilson Cardona-Galeano
Molbank 2023, 2023(4), M1745; https://doi.org/10.3390/M1745 - 27 Nov 2023
Cited by 1 | Viewed by 1186
Abstract
A series of 5-FU-ASA hybrids were synthesized with good yields using click chemistry as the key step. The structures of these compounds were elucidated by spectroscopic analysis. Finally, an optimal pharmacokinetic profile was also estimated for each synthetized hybrid. Taken together, hybrids 4a [...] Read more.
A series of 5-FU-ASA hybrids were synthesized with good yields using click chemistry as the key step. The structures of these compounds were elucidated by spectroscopic analysis. Finally, an optimal pharmacokinetic profile was also estimated for each synthetized hybrid. Taken together, hybrids 4a–h could be used as starting points for further pharmacological studies concerning therapeutic cancer intervention. Full article
(This article belongs to the Section Organic Synthesis)
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5 pages, 1246 KiB  
Short Note
1-(2,5-Dimethoxy-4-nitrophenyl)piperidine
by Tanjia M. Syeda, Muadh R. Al-Shaidi, Ibtihal Basri, Mahboub Merzouk and Fawaz Aldabbagh
Molbank 2023, 2023(4), M1744; https://doi.org/10.3390/M1744 - 27 Nov 2023
Viewed by 1308
Abstract
Treatment of the non-purified mixture of dinitro isomers obtained from the nitration of 1,4-dimethoxybenzene with piperidine led to the isolation of novel but minor adduct, 1-(2,5-dimethoxy-4-nitrophenyl)piperidine (2b) in 15% yield. Yields of nucleophilic aromatic substitution adducts are high when using purified [...] Read more.
Treatment of the non-purified mixture of dinitro isomers obtained from the nitration of 1,4-dimethoxybenzene with piperidine led to the isolation of novel but minor adduct, 1-(2,5-dimethoxy-4-nitrophenyl)piperidine (2b) in 15% yield. Yields of nucleophilic aromatic substitution adducts are high when using purified 1,4-dimethoxy-2,5-dinitrobenzene (1b) with piperidine and pyrrolidine to give (2b) and 1-(2,5-dimethoxy-4-nitrophenyl)pyrrolidine (3b) in 76% and 82% yield, respectively. Full article
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8 pages, 693 KiB  
Communication
Synthesis of Norabietyl and Nordehydroabietyl Imidazolidine-2,4,5-Triones and Their Activity against Tyrosyl-DNA Phosphodiesterase 1
by Kseniya S. Kovaleva, Olga I. Yarovaya, Irina A. Chernyshova, Alexandra L. Zakharenko, Sergey V. Cheresiz, Amirhossein Azimirad, Andrey G. Pokrovsky, Olga I. Lavrik and Nariman F. Salakhutdinov
Molbank 2023, 2023(4), M1743; https://doi.org/10.3390/M1743 - 09 Nov 2023
Viewed by 1254
Abstract
New imidazolidine-2,4,5-triones with norabietic, nordehydroabietic, and adamantane substituents were synthesized by reacting oxalyl chloride and the corresponding ureas, providing good yields. Bioisosteric replacement of the ureide group with a parabanic acid fragment made it possible to increase the solubility of compounds and conduct [...] Read more.
New imidazolidine-2,4,5-triones with norabietic, nordehydroabietic, and adamantane substituents were synthesized by reacting oxalyl chloride and the corresponding ureas, providing good yields. Bioisosteric replacement of the ureide group with a parabanic acid fragment made it possible to increase the solubility of compounds and conduct biological studies. The compounds inhibit the DNA repair enzyme tyrosyl-DNA phosphodiesterase 1 in submicromolar concentrations. Cytotoxic concentrations were also studied on the glioblastoma cell line SNB19. Full article
(This article belongs to the Section Natural Products)
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7 pages, 893 KiB  
Short Note
4,4′,4″-(Benzene-1,3,5-triyltris(ethyne-2,1-diyl))tris(1-methylpyridin-1-ium) Iodide
by Lorenza Romagnoli, Andrea D’Annibale and Alessandro Latini
Molbank 2023, 2023(4), M1742; https://doi.org/10.3390/M1742 - 08 Nov 2023
Viewed by 1219
Abstract
Despite having been known for a long time, quaternary 4,4′-bipyridinium salts, or viologens, are still a highly inspiring class of compounds, thanks to their peculiar redox and charge transfer properties. However, more complex structures containing multiple pyridinium rings, also interspaced by conjugated moieties, [...] Read more.
Despite having been known for a long time, quaternary 4,4′-bipyridinium salts, or viologens, are still a highly inspiring class of compounds, thanks to their peculiar redox and charge transfer properties. However, more complex structures containing multiple pyridinium rings, also interspaced by conjugated moieties, allow an even wider synthetic variability and tunability of their characteristics. The compound described herein is a star-shaped, fully conjugated molecule with three methylated pyridinium rings connected by a triple bond spacer to a central benzene core, which was synthesized from readily available building blocks, representing a quite simple model of multi-pyridyl extended viologen; its UV–visible absorption and fluorescence spectra have also been investigated. Full article
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6 pages, 549 KiB  
Short Note
28-O-Acetyl-3-O’-(Phenylpropynoyl)Betulin
by Ewa Bębenek, Monika Kadela-Tomanek, Beata Filip-Psurska and Elwira Chrobak
Molbank 2023, 2023(4), M1741; https://doi.org/10.3390/M1741 - 24 Oct 2023
Viewed by 1170
Abstract
New derivative of 28-acetylbetulin containing a phenylpropynoyl moiety at the C-3 position was obtained by Steglich method. The chemical structure of this compound has been determined through 1H NMR, 13C NMR, IR, EI MS and HRMS. The antiproliferative effects of 28- [...] Read more.
New derivative of 28-acetylbetulin containing a phenylpropynoyl moiety at the C-3 position was obtained by Steglich method. The chemical structure of this compound has been determined through 1H NMR, 13C NMR, IR, EI MS and HRMS. The antiproliferative effects of 28-O-acetyl-3-O’-(phenylpropynoyl)betulin were evaluated against three human cancer cell lines: T47D (breast cancer), CCRF/CEM (leukemia), SW707 (colorectal adenocarcinoma) and murine cell line P388 (leukemia). The synthesized compound exhibited moderate antiproliferative activity against P388 cells (IC50 = 35.51 µM). The in silico analysis showed that the title compound meets the criteria of Veber’s rule. Full article
(This article belongs to the Section Natural Products)
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5 pages, 513 KiB  
Editorial
Editorial: Special Issue “Molecules from Side Reactions II”
by Stefano D’Errico and Annalisa Guaragna
Molbank 2023, 2023(4), M1740; https://doi.org/10.3390/M1740 - 20 Oct 2023
Viewed by 921
Abstract
This Special Issue, “Molecules from Side Reactions II”, belongs to the section Organic Synthesis of the journal Molbank and was launched in 2021, after the first edition, “Molecules from Side Reactions” [...] Full article
(This article belongs to the Collection Molecules from Side Reactions)
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7 pages, 764 KiB  
Communication
Synthesis and Cholinesterase Inhibitory Potency of 2,3-Indolo-oleanolic Acid and Some Related Derivatives
by Anastasiya V. Petrova, Irina V. Zueva and Konstantin A. Petrov
Molbank 2023, 2023(4), M1739; https://doi.org/10.3390/M1739 - 18 Oct 2023
Viewed by 1110
Abstract
In this study, the synthesis and biological activities of previously and newly synthesized oleanolic acid derivatives containing seven-membered cyclic amines at the C28 position were described. The obtained compounds were fully characterized via 1H and 13C NMR spectroscopy, and the bioactivity [...] Read more.
In this study, the synthesis and biological activities of previously and newly synthesized oleanolic acid derivatives containing seven-membered cyclic amines at the C28 position were described. The obtained compounds were fully characterized via 1H and 13C NMR spectroscopy, and the bioactivity was evaluated by Ellman’s method. Among the tested compounds, 2,3-indolo-oleanolic acid was found to be the most active compound with an IC50 value of 0.78 µM against acetylcholinesterase. These results are significant due to the fact that research on the inhibition of acetylcholinesterase and butyrylcholinesterase enzymes by oleanolic acid, in particular indoloderivatives, is limited. Full article
(This article belongs to the Section Natural Products)
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5 pages, 1260 KiB  
Short Note
2-(1-Methoxycarbonyl-2-phenyleth-1-yl)-1-benzylpyridin-1-ium Bromide
by Lorenzo Suigo, Valentina Straniero and Ermanno Valoti
Molbank 2023, 2023(4), M1738; https://doi.org/10.3390/M1738 - 16 Oct 2023
Viewed by 907
Abstract
In this work, we report the unexpected conversion of a pyridine derivative into the corresponding N-benzylated pyridinium salt due to the presence of unreacted benzyl bromide in the crude product. This transformation was observed at room temperature in a solvent-free environment and [...] Read more.
In this work, we report the unexpected conversion of a pyridine derivative into the corresponding N-benzylated pyridinium salt due to the presence of unreacted benzyl bromide in the crude product. This transformation was observed at room temperature in a solvent-free environment and without any stirring. These interesting data show how pyridinium salts can be formed in mild conditions, avoiding high temperatures that could promote the degradation of the desired product. Full article
(This article belongs to the Collection Molecules from Side Reactions)
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10 pages, 2296 KiB  
Communication
Structural Elucidation of the Triethylammonium Betaine of Squaric Acid
by Paul R. Palme, Richard Goddard, Markus Leutzsch, Adrian Richter, Peter Imming and Rüdiger W. Seidel
Molbank 2023, 2023(4), M1737; https://doi.org/10.3390/M1737 - 16 Oct 2023
Viewed by 1341
Abstract
Betaines of squaric acid have gained research interest because of their structural and spectral properties. We elucidated the crystal and molecular structure of the triethylammonium betaine of squaric acid (1) by X-ray crystallography, IR, and NMR spectroscopy augmented by Hirshfeld surface [...] Read more.
Betaines of squaric acid have gained research interest because of their structural and spectral properties. We elucidated the crystal and molecular structure of the triethylammonium betaine of squaric acid (1) by X-ray crystallography, IR, and NMR spectroscopy augmented by Hirshfeld surface analysis and DFT calculations. The crystal structure determination using Hirshfeld atom refinement reveals that the resonance hybrid structure with partial enolate character of the two lateral squaric acid C=O groups describes 1 best. The solid-state supramolecular structure features weak intermolecular C−H···O hydrogen bonds. The number of C=O bands in the IR spectrum in the solid-state is consistent with local C2v symmetry of the squaric acid residue in 1. The 13C NMR signals of this group in solution were assigned based on 2D NMR experiments and computational prediction using the Gauge-Independent Atom Orbital (GIAO) method. The present study provides the first structural characterization of a betaine of squaric acid containing a four-coordinate nitrogen atom directly attached to the four-membered ring. Full article
(This article belongs to the Section Structure Determination)
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6 pages, 1100 KiB  
Short Note
Diethyl (5-Benzyl-2-(4-(N′-hydroxycarbamimidoyl)phenyl)-5-methyl-4,5-dihydrofuran-3-yl)phosphonate
by Oscar Leonardo Avendaño Leon, Christophe Curti, Fabiana Maia Santos Urbancg Moncorvo, Youssef Kabri, Sébastien Redon, Eduardo Caio Torres-Santos, Romain Paoli-Lombardo and Patrice Vanelle
Molbank 2023, 2023(4), M1736; https://doi.org/10.3390/M1736 - 13 Oct 2023
Cited by 1 | Viewed by 1182
Abstract
As part of our ongoing research into the antileishmanial properties of amidoxime derivatives, we report a preliminary assessment of the antiparasitic properties of a novel compound, diethyl (5-benzyl-2-(4-(N′-hydroxycarbamimidoyl)phenyl)-5-methyl-4,5-dihydrofuran-3-yl)phosphonate. This compound was evaluated in vitro for the first time against the promastigote [...] Read more.
As part of our ongoing research into the antileishmanial properties of amidoxime derivatives, we report a preliminary assessment of the antiparasitic properties of a novel compound, diethyl (5-benzyl-2-(4-(N′-hydroxycarbamimidoyl)phenyl)-5-methyl-4,5-dihydrofuran-3-yl)phosphonate. This compound was evaluated in vitro for the first time against the promastigote form of Leishmania amazonensis. Compounds containing both amidoxime and phosphonyl functional groups in dihydrofuran scaffolds are relatively rare, despite the extensive study of this heterocycle in various biological applications. Therefore, this work makes a valuable contribution to the fight against Leishmania spp. as a neglected disease. The cyclized 4,5-dihydrofuran intermediate scaffold was obtained via a three-step synthetic route that had previously been developed for accessing other derivatives, including the sulfone moiety. This synthesis was performed using a manganese-based free radical oxidative method under microwave irradiation. The intermediary 4,5-dihydrofuran, which included a nitrile group, tolerated the subsequent reaction with hydroxylamine hydrochloride, resulting in the formation of the target product. The target compound showed moderate activity in vitro against the promastigote form of L. amazonensis (IC50 = 91.1 µM). Full article
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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 - 09 Oct 2023
Viewed by 1151
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
(This article belongs to the Collection Heterocycle Reactions)
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6 pages, 961 KiB  
Short Note
(2aR,2a1S,5aR,9bR)-4-Isopropyl-7,8-dimethoxy-2a1-methyl-2,2a,2a1,3,5a,9b-hexahydrofluoreno[9,1-bc]furan
by Irina V. Ilyina, Nikolai S. Li-Zhulanov, Yuri V. Gatilov, Konstantin P. Volcho, Alexander Yu. Sidorenko, Vladimir E. Agabekov and Nariman F. Salakhutdinov
Molbank 2023, 2023(4), M1734; https://doi.org/10.3390/M1734 - 09 Oct 2023
Cited by 1 | Viewed by 912
Abstract
The development of highly efficient methods for the synthesis of chemical products by using renewable raw materials is one of the topical areas of medicinal chemistry. The paper presents the synthesis of (2aR,2a1S,5aR,9bR)-4-isopropyl-7,8-dimethoxy-2a1 [...] Read more.
The development of highly efficient methods for the synthesis of chemical products by using renewable raw materials is one of the topical areas of medicinal chemistry. The paper presents the synthesis of (2aR,2a1S,5aR,9bR)-4-isopropyl-7,8-dimethoxy-2a1-methyl-2,2a,2a1,3,5a,9b-hexahydrofluoreno[9,1-bc]furan. The title compound was obtained through Prins–Friedel–Crafts cascade reactions of trans-4-hydroxymethyl-2-carene, which was synthesized from 3-carene, one of the main components of gum turpentine. The product yield after purification was 48%. The compound’s structure was confirmed by X-ray diffraction analysis. Full article
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6 pages, 1118 KiB  
Short Note
4,4′-([2,2′-Bithiophene]-5,5′-diylbis(ethyne-2,1-diyl))bis(1-methylpyridin-1-ium) Iodide
by Lorenza Romagnoli, Andrea D’Annibale and Alessandro Latini
Molbank 2023, 2023(4), M1733; https://doi.org/10.3390/M1733 - 03 Oct 2023
Viewed by 1134
Abstract
Viologens are a highly advantageous class of compounds for the synthesis of functional materials. Owing to their versatile structure, they can embed additional conjugated moieties, thus representing a convenient platform, for example for organic semiconductors and other energy-related uses. A straightforward synthesis of [...] Read more.
Viologens are a highly advantageous class of compounds for the synthesis of functional materials. Owing to their versatile structure, they can embed additional conjugated moieties, thus representing a convenient platform, for example for organic semiconductors and other energy-related uses. A straightforward synthesis of an extended viologen containing a bithiophene is described here, together with its UV-visible absorption and fluorescence spectroscopy, showing multiple absorption and emission bands. Thanks to its ease of synthesis and optical properties, this organic salt appears to be of potential interest for various optoelectronic applications. Full article
(This article belongs to the Section Organic Synthesis)
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7 pages, 1222 KiB  
Short Note
(3-(4-Chlorophenyl)-4,5-dihydroisoxazol-5-yl)methyl Benzenesulfonate
by Loubna Mokhi, Karim Chkirate, Xiaodong Zhang, Mohsine Driowya and Khalid Bougrin
Molbank 2023, 2023(4), M1732; https://doi.org/10.3390/M1732 - 22 Sep 2023
Viewed by 979
Abstract
A novel single crystal of (3-(4-chlorophenyl)-4,5-dihydroisoxazol-5-yl)methyl benzenesulfonate has been synthetized via a one-pot sequential strategy under sonication. The single crystal has been investigated using X-ray diffraction analysis. Hydrogen bonding between C–H···O and C–H···N produces a layer structure in the crystal. According to a [...] Read more.
A novel single crystal of (3-(4-chlorophenyl)-4,5-dihydroisoxazol-5-yl)methyl benzenesulfonate has been synthetized via a one-pot sequential strategy under sonication. The single crystal has been investigated using X-ray diffraction analysis. Hydrogen bonding between C–H···O and C–H···N produces a layer structure in the crystal. According to a Hirshfeld surface analysis, interactions H···H (28.9%), H···O/O···H (26.7%) and H···C/C···H (15.8%) make the largest contributions to crystal packing. The optimized structure and the solid-state structure that was obtained through experiments are compared using density functional theory at the B3LYP/6-311 G + (d,p) level. The computed energy difference between the lowest unoccupied molecular orbital (LUMO) and highest occupied molecular orbital (HOMO) is 4.6548 eV. Full article
(This article belongs to the Topic Towards the Sustainable Synthesis of Biologically Active Molecules in Green Solvents)
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