ChemInform Abstract: Synthesis and Antimycobacterial Activity of Some New 3‐Heterocyclic Substituted Chromones.

Gašparová, Renata; Lácová, Margita; El‐Shaaer, Hafez M.; Odlerova, Z.

doi:10.1002/chin.199744154

Cited by 6 publications

(10 citation statements)

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“…1b,c reacted with 2-methylbenzimidazole 29a and 2-methylbenzothiazole 29b in dry DMSO and boric acid to give the addition products 30a,b when the reactiontook place at 60 °C, but when the reaction took place at 120 °C afforded the condensation products 31a,b (Scheme 13) [32].…”

Section: -Formylchromonesmentioning

confidence: 99%

3-Formylchromones as diverse building blocks in heterocycles synthesis

et al. 2013

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Section: -Formylchromonesmentioning

confidence: 99%

3-Formylchromones as diverse building blocks in heterocycles synthesis

et al. 2013

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“…The experimental IR frequencies of C=O groups of coumarin derivatives were compared with theoretical bond lengths of C=O groups which were obtained from molecular mechanical calculations on the basis of the semi-empirical AM1 and Ab Initio (STO-3G) methods of HyperChem 8.03 computer program after geometrical optimization of the structures for compounds (2)(3)(4)(5)(6)(7)(8)(9)(10)(11)(12) (Table 1). Table 1.…”

Section: Molecular Orbital Calculationsmentioning

confidence: 99%

“…-Benzopyrone derivatives constitute an important class of oxygenated heterocycles [1]. Many compounds containing the benzopyrone nucleus, both naturally occurring and synthetic, are known to exhibit pharmacological activity such as antifungal [2][3][4], antibacterial [5], anti-mycobacterial [6,7], anticoagulants [8,9], inhibitors of some enzymes [10,11], and antitumor [12][13][14]. With the expectations to find biological activity, we decided to investigate the synthesis of some novel systems of -benzopyrone derivatives bearing fused and isolated moiety.…”

Section: Introductionmentioning

confidence: 99%

An efficient cyclocondensation reactions, antimicrobial activity and molecular orbital calculations of α-benzopyrone derivatives

et al. 2012

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An efficient synthesis of 4,6,8-trimethyl-2-oxo-2H-chromene-3-carbonitrile (2) via Claisen condensation of 3,5-dimethyl-2-hydroxyacetophenone with ethyl cyanoacetate in the presence of sodium metal is reported. Cyclocondensation reactions of compound (2) with ethyl acetate or with ethyl cyanoacetate in the presence of ethoxide gave sodium salt of 7-amino-9-hydroxy-2,4-dimethyl-6H-benzo[c]chromen-6-one derivatives (3) and (4) respectively, which upon neutralization with 10 % hydrochloric acid gave 7-amino-9hydroxy-2,4-dimethyl-6H-benzo[c]chromen-6-one (5). Hydrolysis of compound (2) with ethanolic sodium hydroxide solution gave 4,6,8-trimethyl-2-oxo-2H-chromene-3-carboxylic acid (6). Treatment of compound (2) with Vilsmier reagent using excess POCl3 gave 4-(chloro(formyl)methyl-6,8-dimethyl-2-oxo-2H-chromene-3-carbonitrile (7). Also, condensation of compound (2) with DMF-DMA in xylene or with POCl3/DMF in pyridine gave the same product 4-((E)-2-(dimethylamino)vinyl)-6,8-dimethyl-2-oxo-2H-chromene-3-carbonitrile (8). The cyclocondensation reactions of compound (8) with hydroxylamine hydrochloride, urea, and with hydrazinecarbodithioic acid gave 3,4-dihydro-3-hydroxy-4imino-7,9-dimethylchromeno[3,4-c]pyridin-5-one (9), 4-imino-7,9-dimethyl-5-oxo-4H-chromeno[3,4-c]pyridine-3(5H)-carboxamide (10) and 3-amino-3,4-dihydro-4-imino-7,9-dimethyl chromeno[3,4-c]pyridin-5-one (11), respectively. Also, acid hydrolysis of compound (8) gave 7,9-dimethyl-3H-chromeno[3,4-c]pyridine-4,5-dione (12). Structures of the products were established on the basis of elemental analysis, IR, 1 H and 13 C NMR, mass spectra and semiempirical AM1-MO calculations. The antimicrobial activities of the synthesized products were also studied. Synthesis α-Benzopyrone Cyclocondensation Antimicrobial Activity Chromeno[3,4-c]pyridinones Molecular orbital calculations

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“…3‐Substituted 4‐oxo‐4 H ‐1‐benzopyrane derivatives are known as useful building blocks for various heterocycles due to their reactivity towards nucleophiles or ability to rearrange under mild conditions . A large number of 4‐oxo‐4 H ‐1‐benzopyrane derivatives occur widely in nature and exhibit variety of biological activities, for example, antialgal , antifungal, antiparasitic , or antimycobacterial .…”

Section: Introductionmentioning

confidence: 99%

Study of the Reactivity of 6,8‐Dimethyl‐4‐oxo‐4H‐1‐benzopyran‐3‐carboxaldehyde Towards Amino‐6‐oxopyridine‐3‐carboxylate Derivatives

El‐Shaaer

Abdel-Monem

Ibrahim

et al. 2014

Journal of Heterocyclic Chem

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The condensation reactions of 6,8‐dimethyl‐4‐oxo‐4H‐1‐benzopyran‐3‐carboxaldehyde (1) with equimolar amounts of ethyl 2‐amino‐4‐(4‐chlorophenyl)‐5‐cyano‐1‐[(5,6‐diphenyl‐1,2,4‐triazin‐3‐yl)amino]‐6‐oxo‐1,6‐dihydropyridine‐3‐carboxylate (2) at different reaction conditions gave different chromanone and chromenone products 3, 4, 5. Also, the condensation reactions of compound 1 with ethyl 5‐cyano‐1,2‐diamino‐4‐(3‐nitrophenyl)‐6‐oxo‐1,6‐dihydropyridine‐3‐carboxylate (6) in absolute ethanol, dry benzene, acetic acid, and/or dry xylene gave a variety of products 7, 8, 9, 10 depending on the solvent used.

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ChemInform Abstract: Synthesis and Antimycobacterial Activity of Some New 3‐Heterocyclic Substituted Chromones.

Cited by 6 publications

References 0 publications

3-Formylchromones as diverse building blocks in heterocycles synthesis

3-Formylchromones as diverse building blocks in heterocycles synthesis

An efficient cyclocondensation reactions, antimicrobial activity and molecular orbital calculations of α-benzopyrone derivatives

Study of the Reactivity of 6,8‐Dimethyl‐4‐oxo‐4H‐1‐benzopyran‐3‐carboxaldehyde Towards Amino‐6‐oxopyridine‐3‐carboxylate Derivatives

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