A simple and an efficient approach to the synthesis of a special tautomer of 1,3-thiazinones and 1,3-oxazinones

Sheibani, Hassan; Mosslemin, Mohammad Hossein; Behzadi, Soheila; Islami, Mohammad Reza; Foroughi, Habibollah; Saidi, Kazem

doi:10.3998/ark.5550190.0006.f13

Cited by 15 publications

(1 citation statement)

References 14 publications

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“…Melting 2-(1-Substituted ethylidene)hydrazinecarbothioamides 1a-h were prepared by condensation of 4-phenylthiosemicarbazide with the appropriate ketones according to the published procedures. 21,22 Dimethyl acetylenedicarboxylate (DMAD, 2) was bought from Fluka.…”

Section: Methodsmentioning

confidence: 99%

Synthesis and Antibacterial Activity of New Substituted Ethylidenehydrazinylidene-1,3-thiazol-4-ones

Hassan

Mohamed

et al. 2014

Journal of Chemical Research

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A series of substituted ethylidenehydrazinylidene-1,3-thiazol-4-ones and dimethyl 2-{[4-1(-[5-(2-methoxy-2-oxoethylidene)-4-oxo-3-phenyl-1,3-(thiazolidin-2-ylidene]hydrazonylidene}ethyl)phenyl]aminofumarate were synthesised by condensation of substituted ethylidene-N-phenylhydrazinecarbothioamides with dimethyl acetylenedicarboxylate. The synthesised compounds were characterised by spectroscopic methods and confirmed by single crystal X-ray crystallography. Some of the prepared compounds were screened for their in vitro antibacterial activity against different strains of microorganisms, compound 3b exhibited significant antibacterial activity against Pseudomonas aeruginosa compared to ciprofloxacin with MIC value of 1.12 µg mL -1 .

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Section: Methodsmentioning

confidence: 99%

Synthesis and Antibacterial Activity of New Substituted Ethylidenehydrazinylidene-1,3-thiazol-4-ones

Hassan

Mohamed

et al. 2014

Journal of Chemical Research

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Synthesis and Antibacterial Activity of 4‐Aryl‐2‐(1‐substituted ethylidene)thiazoles

Hassan

Ibrahim

El‐Sheref

et al. 2013

Archiv der Pharmazie

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(E)-4-Aryl-2-[2-(1-substituted ethylidene)hydrazinyl]thiazoles and (Z)-3-substituted-4-aryl-2-[(E)-(1-phenylethylidene)hydrazono]-2,3-dihydrothiazoles were synthesized by the reaction of (substituted ethylidene)hydrazinecarbothioamides with ω-bromoacetophenones. The characterization of this new class of compounds was performed using different spectroscopic tools. The structure of (Z)-3-benzyl-4-(4-bromophenyl)-2-[(E)-(1-phenylethylidene)hydrazono]-2,3-dihydrothiazole 6e was unambiguously confirmed by single-crystal X-ray crystallography. Compounds 5a-e, 5i, 6e, 6g, and 6i were screened for their in vitro antibacterial activity against different strains of microorganisms; most of the tested compounds exhibited promising antibacterial activity against some organisms compared to ciprofloxacin and sulbactam penicillin. Compounds 5e, 5i, 6e, 6g, and 6i exhibited several-fold significant antibacterial activity against the Gram-positive bacteria Staphylococcus aureus, better than ciprofloxacin, with minimum inhibitory concentration values ranging from 0.05 to 0.4 µg/mL. The rest of the tested compounds gave significant antibacterial activities against different Gram-negative bacterial strains.

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The reaction of (chlorocarbonyl)phenyl ketene with enaminones: A novel synthesis of some 5‐acyl‐4‐hydroxy‐2‐(1H)‐pyridinones and 7‐hydroxy‐5‐oxo‐1,4‐diazepin derivative

Abaszadeh

Sheibani

Saidi

2009

Journal of Heterocyclic Chem

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A series of substituted 5‐acyl‐4‐hydroxy‐2‐(1H)‐pyridinone derivatives has been prepared in a one‐step procedure from condensation of (chlorocarbonyl)phenyl ketene with some enaminones which were prepared from 1,3‐diketones, such as 2,4‐pentanedione, 1‐phenyl‐1,3‐butanedione, and ethyl acetoacetate in boiling toluene as a solvent. A mechanism is presented to account for the formation of the products. The overall sequence provides a simple and efficient route to prepare 3,4,5,6‐tetrasubstituted 2‐(1H)‐pyridinone in good to excellent yields and in a short experimental time. J. Heterocyclic Chem., (2009).

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A simple and an efficient approach to the synthesis of a special tautomer of 1,3-thiazinones and 1,3-oxazinones

Cited by 15 publications

References 14 publications

Synthesis and Antibacterial Activity of New Substituted Ethylidenehydrazinylidene-1,3-thiazol-4-ones

Synthesis and Antibacterial Activity of New Substituted Ethylidenehydrazinylidene-1,3-thiazol-4-ones

Synthesis and Antibacterial Activity of 4‐Aryl‐2‐(1‐substituted ethylidene)thiazoles

The reaction of (chlorocarbonyl)phenyl ketene with enaminones: A novel synthesis of some 5‐acyl‐4‐hydroxy‐2‐(1H)‐pyridinones and 7‐hydroxy‐5‐oxo‐1,4‐diazepin derivative

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