Molbank

Open AccessShort Note

4-Amino-3-(1-{[amino(3-methyl-2-oxido-1,2,5-oxadiazol-4-yl)methylene]hydrazinylidene}ethyl)-1,2,5-oxadiazole 2-Oxide

by

Margarita A. Epishina

,

Alexander S. Kulikov

and

Leonid L. Fershtat

Molbank 2022, 2022(3), M1425; https://doi.org/10.3390/M1425 - 12 Aug 2022

Abstract

Functionally substituted 1,2,5-oxadiazole 2-oxides (furoxans) are important pharmaceutical scaffolds used for the preparation of various pharmacologically active substances. Furoxans bearing hydrazone functionality are considered as promising drug candidates for the treatment of neglected diseases. However, pharmacologically oriented hydrazones derived from (furoxanyl)amidrazones and acetylfuroxans [...] Read more.

Functionally substituted 1,2,5-oxadiazole 2-oxides (furoxans) are important pharmaceutical scaffolds used for the preparation of various pharmacologically active substances. Furoxans bearing hydrazone functionality are considered as promising drug candidates for the treatment of neglected diseases. However, pharmacologically oriented hydrazones derived from (furoxanyl)amidrazones and acetylfuroxans have remained unknown so far. In this communication, a simple method for the synthesis of 4-amino-3-(1-{[amino(3-methyl-2-oxido-1,2,5-oxadiazol-4-yl)methylene]hydrazinylidene}ethyl)-1,2,5-oxadiazole 2-oxide is described. The structure of the synthesized compound was established by elemental analysis, high-resolution mass spectrometry, ¹H, ¹³C NMR and IR spectroscopy. Full article

(This article belongs to the Special Issue Heteroatom Rich Organic Heterocycles)

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Scheme 1

Open AccessShort Note

Diethyl(benzamido(diisopropoxyphosphoryl)methyl) phosphonate

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Molbank 2022, 2022(3), M1424; https://doi.org/10.3390/M1424 (registering DOI) - 11 Aug 2022

Abstract

Bisphosphonates are widely used in medicine and related areas, mainly for the treatment of bone diseases, such as osteoporosis. However, their synthesis is usually performed under harsh reaction conditions. In order to overcome this limitation, the present work illustrates a new synthetic route [...] Read more.

Bisphosphonates are widely used in medicine and related areas, mainly for the treatment of bone diseases, such as osteoporosis. However, their synthesis is usually performed under harsh reaction conditions. In order to overcome this limitation, the present work illustrates a new synthetic route to access the title α-aminobisphosphonate in milder reaction conditions using α-phosphorylated imines as key intermediates. Full article

(This article belongs to the Topic Organocatalysis and Transition-Metal Catalysis: Key Trends in Synthetic Chemistry and Challenges)

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Figure 1

Open AccessShort Note

N,N-Bis(7-nitrobenz[c][1,2,5]oxadiazol-4-yl)cystamine

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Molbank 2022, 2022(3), M1423; https://doi.org/10.3390/M1423 - 08 Aug 2022

Abstract

Background: New amino derivatives of NBD type are of high interest due to their strong fluorescence, while compounds containing a disulphide moiety are of high interest in nano-chemistry due to their easiness of attaching to noble nanoparticles. Therefore, in this work a new [...] Read more.

Background: New amino derivatives of NBD type are of high interest due to their strong fluorescence, while compounds containing a disulphide moiety are of high interest in nano-chemistry due to their easiness of attaching to noble nanoparticles. Therefore, in this work a new fluorescent derivative of NBD and cystamine was obtained. Methods: The reaction between cystamine and NBD-chloride occurs straightforwardly, and the isolated new compound was characterized by IR, UV-Vis, fluorescence, ¹H- and ¹³C-NMR, MS, etc. Results: Structural analysis confirmed the proposed structure and highlighted the fluorescence behavior. Conclusions: A new fluorescent derivative of cystamine was obtained and characterized by different means. Full article

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Open AccessCommunication

Placovinane: 1″β-Ethoxy-6,4′-dimethoxy-3″,3″-dimethyl-1″,2″-dihydropyranoisoflavone, a New Isoflavone Derivative

by

Tuyet T. N. Huynh

,

Lien T. M. Do

and

Jirapast Sichaem

Molbank 2022, 2022(3), M1422; https://doi.org/10.3390/M1422 - 05 Aug 2022

Abstract

Isoflavonoids possess a 3-phenylchroman skeleton and are the biologically active secondary metabolites of various plants that are used for different health promoting and restoring effects through a variety of mechanisms. Chromatographic separation of the n-hexane extract from the stems of Placolobium vietnamense [...] Read more.

Isoflavonoids possess a 3-phenylchroman skeleton and are the biologically active secondary metabolites of various plants that are used for different health promoting and restoring effects through a variety of mechanisms. Chromatographic separation of the n-hexane extract from the stems of Placolobium vietnamense led to the isolation of a new isoflavone derivative, placovinane (1), together with four known compounds (2–5). The structures of isolated compounds were identified from their spectroscopic data and by comparison with the literature. All isolated compounds were evaluated for their α-glucosidase inhibition. They all exhibited potent α-glucosidase inhibition with IC₅₀ values ranging from 11.0 to 87.3 µM, which was significantly less than the positive control acarbose (IC₅₀ 179 µM). The cytotoxicity of 1 was evaluated against KB, Hep G2, and MCF7 cell lines, and displayed weak cytotoxicity toward KB and Hep G2 cell lines, with the IC₅₀ values of 89.6 and 93.8 μM, respectively. Full article

(This article belongs to the Section Natural Products)

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Figure 1

Open AccessShort 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 - 05 Aug 2022

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

(This article belongs to the Collection Heterocycle Reactions)

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Open AccessShort Note

2,5-Bis((E)-2-ferrocenylvinyl)-N,N,N′,N′-tetrapropylbenzene-1,4-diamine

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Molbank 2022, 2022(3), M1420; https://doi.org/10.3390/M1420 - 04 Aug 2022

Abstract

The synthesis and spectroscopic investigation of an acidochromic phenylenevinylene dye with two ferrocene groups is presented. Full article

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Graphical abstract

Open AccessShort Note

3-[(1H-Benzo[d][1,2,3]triazol-1-yl)oxy]propyl 9-hydroxy-5a,5b,8,8,11a-pentamethyl-1-(prop-1-en-2-yl)icosahydro-3aH-cyclopenta[a]chrysene-3a-carboxylate

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Alessandra Gianoncelli

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Paolo Coghi

and

Giovanni Ribaudo

Molbank 2022, 2022(3), M1419; https://doi.org/10.3390/M1419 - 04 Aug 2022

Abstract

We herein report on the synthesis of a pentacyclic triterpene functionalized through derivation of betulinic acid with hydroxybenzotriazole. The compound was fully characterized by proton (¹H-NMR), carbon-13 (¹³C-NMR), heteronuclear single quantum coherence (HSQC) and distortionless enhancement by polarization transfer [...] Read more.

We herein report on the synthesis of a pentacyclic triterpene functionalized through derivation of betulinic acid with hydroxybenzotriazole. The compound was fully characterized by proton (¹H-NMR), carbon-13 (¹³C-NMR), heteronuclear single quantum coherence (HSQC) and distortionless enhancement by polarization transfer (DEPT-135 and DEPT-90) nuclear magnetic resonance. Ultraviolet (UV), and Fourier-transform infrared (FTIR) spectroscopies as well as and high-resolution mass spectrometry (HRMS) were also adopted. Computational studies were conducted to foresee the interactions between compound 3 and phosphodiesterase 9, a relevant target in the field of neurodegenerative diseases. Additionally, preliminary calculation of physico-chemical descriptors was performed to evaluate the drug-likeness of compound 3. Full article

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Open AccessShort Note

12H-Dibenzo[d,g][1,2,3]triselenocin-12-ol

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Molbank 2022, 2022(3), M1418; https://doi.org/10.3390/M1418 - 01 Aug 2022

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

(This article belongs to the Collection Heterocycle Reactions)

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Open AccessCommunication

An Efficient Synthesis of Novel 4-Aryl-2-thioxo-3,4-dihydro-1H-pyrimido[1,2-a][1,3,5]triazin-6(2H)-ones and Their Antibacterial Activity

by

Do Van Quy

,

Nguyen Van Hung

,

Nadezhda Stolpovskaya

,

Aleksey Kruzhilin

,

Svetlana S. Olshannikova

,

Marina Holyavka

,

Vladimir Sulimov

and

Khidmet Shikhaliev

Molbank 2022, 2022(3), M1417; https://doi.org/10.3390/M1417 - 30 Jul 2022

Abstract

New substituted 4-aryl-8-methyl-2-thioxo-1,2,3,4-tetrahydro-6H-pyrimido[1,2-a][1,3,5]triazin-6-one 8a–b and ethyl 4-aryl-6-oxo-2-thioxo-1,3,4,6-tetrahydro-2H-pyrimido[1,2-a][1,3,5]triazine-7-carboxylate 8c–e were synthesized by the reaction of the corresponding 4-oxopyrimidin-2-ylthioureas with arylaldehydes. The formation of only one regioisomer was proven using complex spectral data and its structure was [...] Read more.

New substituted 4-aryl-8-methyl-2-thioxo-1,2,3,4-tetrahydro-6H-pyrimido[1,2-a][1,3,5]triazin-6-one 8a–b and ethyl 4-aryl-6-oxo-2-thioxo-1,3,4,6-tetrahydro-2H-pyrimido[1,2-a][1,3,5]triazine-7-carboxylate 8c–e were synthesized by the reaction of the corresponding 4-oxopyrimidin-2-ylthioureas with arylaldehydes. The formation of only one regioisomer was proven using complex spectral data and its structure was characterized. It was found that the interaction of 6-amino-4-phenyl-3,4-dihydro-1,3,5-triazine-2(1H)-thione with ethyl acetoacetate and diethyl ethoxymethylenemalonate leads to the formation of the same regioisomer. That is, changing the sequence of stages in this cascade process does not affect the structure of the final reaction product. All synthesized compounds exhibit antibacterial activity against E. coli and S. aureus cultures at a concentration (MIC) of 256 µg/mL. Full article

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Open AccessCommunication

Activation–Deactivation of Inter-Peptide Bond in Fluoro-N-(2-hydroxy-5-methyl phenyl)benzamide Isomers, Induced by the Position of the Halogen Atom in the Benzene Ring

by

Rodolfo Moreno-Fuquen

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Molbank 2022, 2022(3), M1416; https://doi.org/10.3390/M1416 - 29 Jul 2022

Abstract

The synthesis and XRD characterization at 295 K of three isomers, X-fluoro-N-(2-hydroxy-5-methyl phenyl) benzamide: (o-FPhB), (m-FPhB), and (p-FPhB), are presented. o-FPhB and m-FPhB show high structural affinity concerning molecular and packing structures. [...] Read more.

The synthesis and XRD characterization at 295 K of three isomers, X-fluoro-N-(2-hydroxy-5-methyl phenyl) benzamide: (o-FPhB), (m-FPhB), and (p-FPhB), are presented. o-FPhB and m-FPhB show high structural affinity concerning molecular and packing structures. The planarity of the C1-C7(O1)-N1-C8 peptide bond in o-FPhB, and m-FPhB confers high stability, favoring its tendency to acquire a resonant structure in the peptide segment and in the molecule. For p-FPhB, a stereochemical gate opens, leading to the activation of N-H∙∙∙∙O interpeptide bonds, defining its supramolecular properties. Active participation of the halogen in the assembly of the structures is observed, forming intramolecular rings and molecule chains during crystal growth. The o-FPhB and m-FPhB form parallel sheets that develop hydrogen C-H···Cg, halogen C-F···Cg, or C=O···Cg interactions. Theoretical evaluations of the properties performed by the DFT/B3LYP/(6-311G(d,p) showed good agreement with the experimental values. The IR analysis reaffirms the presence of N-H, C=O, O-H, C-F, and C-H. In the UV-Vis, an increase in the energetic stability, O···H interactions, and electrostatic potential in the NH region reaffirm the disposition of p-FPhB for the formation of the N-H···O interpeptide bond. A molecular docking on the benzamides involving protein receptors showed similar behavior for all three isomers. Full article

(This article belongs to the Section Structure Determination)

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Graphical abstract

Open AccessShort Note

3,6-Dichlorobenzene-1,2,4,5-tetraol

by

R. Alan Aitken

,

Niti Schindler

and

Alexandra M. Z. Slawin

Molbank 2022, 2022(3), M1415; https://doi.org/10.3390/M1415 - 29 Jul 2022

Abstract

The X-ray structure of the title compound as the monohydrate has been determined and shows a complex structure with two independent molecules each of the compound and water and eleven distinct hydrogen bonding interactions. Its melting point has also been recorded for the [...] Read more.

The X-ray structure of the title compound as the monohydrate has been determined and shows a complex structure with two independent molecules each of the compound and water and eleven distinct hydrogen bonding interactions. Its melting point has also been recorded for the first time. Full article

(This article belongs to the Section Structure Determination)

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Graphical abstract

Open AccessCommunication

2-Hydroxy-3-(1-(4-vinylbenzyl)imidazol-3-ium-3-yl)propane-1-sulfonate and 3-(4-Vinylbenzyl)dimethylammonio)-2-hydroxypropane-1-sulfonate as New Zwitterionic Monomers

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Bénédicte Lepoittevin

Molbank 2022, 2022(3), M1414; https://doi.org/10.3390/M1414 - 26 Jul 2022

Abstract

Zwitterionic polymers emerge as very useful materials for applications in antifouling surfaces. The properties of these polymers can be tuned by variations of the chemical structure of the corresponding monomer. In this study, two zwitterionic ammonium sulfonate monomers, bearing hydroxyl function and styrenic [...] Read more.

Zwitterionic polymers emerge as very useful materials for applications in antifouling surfaces. The properties of these polymers can be tuned by variations of the chemical structure of the corresponding monomer. In this study, two zwitterionic ammonium sulfonate monomers, bearing hydroxyl function and styrenic polymerizable groups, were prepared in two steps. The two monomers were obtained using 4-vinylbenzyl chloride as the key precursor. The zwitterionic monomers were characterized by ¹H NMR, ¹³C NMR, IR spectroscopy, and high-resolution mass spectrometry (HRMS). These two monomers enable the preparation of novel zwitterionic polymers with enhanced hydrophilicity, due to the presence of a hydroxyl group. Full article

(This article belongs to the Section Organic Synthesis)

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Graphical abstract

Open AccessShort Note

[4-(3,4-Dimethoxyphenyl)-3,6-dimethyl-2-phenyl-3,4-dihydroquinolin-1(2H)-yl)](furan-2-yl)methanone

by

Sandra M. Bonilla-Castañeda

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Andrés F. Villamizar-Mogotocoro

and

Vladimir V. Kouznetsov

Molbank 2022, 2022(3), M1413; https://doi.org/10.3390/M1413 - 25 Jul 2022

Abstract

A N-(2,4-diaryltetrahydroquinolin-1-yl) furan-2-carboxamide derivative, [4-(3,4-dimethoxyphenyl)-3,6-dimethyl-2-phenyl-3,4-dihydroquinolin-1(2H)-yl)](furan-2-yl)methanone, was synthesized in a two-step procedure from p-toluidine, benzaldehyde, and trans-methyl-isoeugenol as commercial starting reagents through a sequence of Povarov cycloaddition reaction/N-furoylation processes. The structure of the compound was fully characterized [...] Read more.

A N-(2,4-diaryltetrahydroquinolin-1-yl) furan-2-carboxamide derivative, [4-(3,4-dimethoxyphenyl)-3,6-dimethyl-2-phenyl-3,4-dihydroquinolin-1(2H)-yl)](furan-2-yl)methanone, was synthesized in a two-step procedure from p-toluidine, benzaldehyde, and trans-methyl-isoeugenol as commercial starting reagents through a sequence of Povarov cycloaddition reaction/N-furoylation processes. The structure of the compound was fully characterized by IR, ¹H, ¹³C-NMR, and X-ray diffraction data. Such types of derivatives are known as relevant therapeutic agents exhibiting potent anticancer, antibacterial, antifungal, anti-inflammatory, and immunological modulator properties. Full article

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Graphical abstract

Open AccessShort Note

5,5′-(Piperazine-1,4-diyl)bis(4-chloro-3H-1,2-dithiol-3-one)

by

Vladimir A. Ogurtsov

and

Oleg A. Rakitin

Molbank 2022, 2022(3), M1411; https://doi.org/10.3390/M1411 - 20 Jul 2022

Abstract

Conjugates of 3H-1,2-dithiol-3-ones with various biologically active compounds are intensively investigated. Although many derivatives of this class have been described in the literature, the compounds containing two dithiole cycles have been explored much less. In this communication, it was shown that [...] Read more.

Conjugates of 3H-1,2-dithiol-3-ones with various biologically active compounds are intensively investigated. Although many derivatives of this class have been described in the literature, the compounds containing two dithiole cycles have been explored much less. In this communication, it was shown that the reaction of 4,5-dichloro-3H-1,2-dithiol-3-one with piperazine can selectively lead to the mono-product, 4-chloro-5-piperazin-1-yl-3H-1,2-dithiol-3-one and bis-product, 5,5′-(piperazine-1,4-diyl)bis(4-chloro-3H-1,2-dithiol-3-one). The structure of the synthesized compounds was established by elemental analysis, high resolution mass-spectrometry, ¹H, ¹³C NMR and IR spectroscopy, and mass-spectrometry. Full article

(This article belongs to the Section Organic Synthesis)

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Open AccessShort Note

3,6-Dihydro-5H-pyrazolo [4′,3′:5,6]pyrano[3,4-b]indol-5-one

by

Amalia D. Kalampaliki

,

Sofia Kanellopoulou

and

Ioannis K. Kostakis

Molbank 2022, 2022(3), M1412; https://doi.org/10.3390/M1412 - 20 Jul 2022

Abstract

Pyrano [3,4-b]indol-1(9H)-ones and indolo [2,3-c]coumarins are important classes of heterocyclic compounds with versatile biological activities. Herein, we describe a straightforward and scalable synthesis of 3,6-dihydro-5H-pyrazolo [4′,3′:5,6]pyrano [3,4-b]indol-5-one, a pyrazolo-fused pyrano [3,4-b]indolone, [...] Read more.

Pyrano [3,4-b]indol-1(9H)-ones and indolo [2,3-c]coumarins are important classes of heterocyclic compounds with versatile biological activities. Herein, we describe a straightforward and scalable synthesis of 3,6-dihydro-5H-pyrazolo [4′,3′:5,6]pyrano [3,4-b]indol-5-one, a pyrazolo-fused pyrano [3,4-b]indolone, via a three step approach including Fischer-indole synthesis and intramolecular esterification. The compound is fully characterized by means of ¹H and ¹³C NMR spectra, using direct and long-range heteronuclear correlation experiments (HMBC and HMQC). Full article

(This article belongs to the Section Organic Synthesis)

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Graphical abstract

Open AccessShort Note

rel-2-[4-Chloro-2-[(5R,6R,7S)-6-[5-(4-methoxyphenyl)-3-(2-naphthyl)-3,4-dihydropyrazole-2-carbonyl]-5-methyl-2-oxo-3,5,6,7-tetrahydrothiopyrano[2,3-d]thiazol-7-yl]phenoxy]acetic Acid

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Molbank 2022, 2022(3), M1410; https://doi.org/10.3390/M1410 - 19 Jul 2022

Abstract

The hetero-Diels–Alder reaction is the main synthetic tool for obtaining pharmacological agents with a thiopyrano[2,3-d]thiazole motif. In the present work, an efficient method for the synthesis of pyrazoline-containing thiopyrano[2,3-d]thiazole is described. The pyrazoline-bearing dienophile was proposed and used as [...] Read more.

The hetero-Diels–Alder reaction is the main synthetic tool for obtaining pharmacological agents with a thiopyrano[2,3-d]thiazole motif. In the present work, an efficient method for the synthesis of pyrazoline-containing thiopyrano[2,3-d]thiazole is described. The pyrazoline-bearing dienophile was proposed and used as effective building block for the synthesis of the title compound. The structure of the synthesized rel-2-[4-chloro-2-[(5R,6R,7S)-6-[5-(4-methoxyphenyl)-3-(2-naphthyl)-3,4-dihydropyrazole-2-carbonyl]-5-methyl-2-oxo-3,5,6,7-tetrahydrothiopyrano[2,3-d]thiazol-7-yl]phenoxy]acetic acid (3) was confirmed by ¹H, ¹³C, 2D NMR, and LC-MS spectra. Anticancer activity in “60 lines screening” (NCI DTP protocol) was studied in vitro for the title compound. Full article

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Graphical abstract

Open AccessCommunication

Synthesis of 1-[1H,1H,2H,2H-perfluooctyl]-3-[2-(oxiran-2-yl)ethyl]imidazolium 4-[(2-oxiran-2-yl)ethoxy]benzenesulfonate as a New Perfluorinated Ionic Monomer

by

Tony Kui

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Sébastien Livi

and

Jérôme Baudoux

Molbank 2022, 2022(3), M1409; https://doi.org/10.3390/M1409 - 15 Jul 2022

Abstract

Access to perfluorinated compounds represents a growing challenge in the academic and industrial fields to achieve target compounds with specific physico-chemical properties. Especially, the insertion of a perfluorinated chain within an ionic liquid can provide improvements not just in terms of hydrophobicity and [...] Read more.

Access to perfluorinated compounds represents a growing challenge in the academic and industrial fields to achieve target compounds with specific physico-chemical properties. Especially, the insertion of a perfluorinated chain within an ionic liquid can provide improvements not just in terms of hydrophobicity and lipophobicity, but also viscosity, density as well as thermal stability. In this research area, we have recently developed new access points to several epoxy imidazolium salts combined with fluorinated anions such as bistriflimide (NTf₂⁻), hexafluorophosphate (PF₆⁻) or tetrafluoroborate (BF₄⁻). Here, we reported the synthesis of a perfluorinated imidazolium cation associated with a sulfonate anion as a new functionalized partner. This sequence required four steps from imidazole (cationic part) and three steps from sodium 4-hydroxybenzenesulfonate (anionic part), respectively. This perfluorinated ionic liquid was fully characterized by nuclear magnetic resonance with ¹H-NMR, ¹⁹F-NMR, ¹³C-NMR, DEPT, COSY, HSQC, HMBC and IR spectroscopy. The two parts of the salt were confirmed by high-resolution mass spectrometry (HRMS), and we combined thermogravimetric analysis (TGA) and differential scanning calorimetry (DSC) to determine the thermal properties of this new compound. Full article

(This article belongs to the Section Organic Synthesis)

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Open AccessShort 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

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

(This article belongs to the Collection Heterocycle Reactions)

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Open AccessCommunication

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

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

(This article belongs to the Collection Heterocycle Reactions)

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