Synthesis and characterization of selected fused isoxazole and pyrazole derivatives and their antimicrobial activity

Synthesis and characterization of selected fused isoxazole and pyrazole derivatives and their antimicrobial activity

New potent antibacterials, fused isoxazole and pyrazole derivatives, were synthesized using 5,5-dimethylcyclohexane-1,3-dione (1) and 3-[(4-chlorobenzylidene)amino]-2-thioxoimidazolidin-4-one (2) as synthons. Aromatic aldehydes on condensation with 1 and 2 gave 2-arylidene-5,5-dimethylcyclohexane-1,...

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Bibliographic Details
Published in:Journal of the Serbian Chemical Society Vol. 74; no. 11; pp. 1219 - 1228
Main Authors: VIJAY V. DABHOLKAR, FAISAL Y. ANSARI
Format: Journal Article
Language:English
Published: Serbian Chemical Society 01-01-2009
Subjects:
antibacterial activity
dimedone
isoxazole
pyrazole
thiohydantoin
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Summary:New potent antibacterials, fused isoxazole and pyrazole derivatives, were synthesized using 5,5-dimethylcyclohexane-1,3-dione (1) and 3-[(4-chlorobenzylidene)amino]-2-thioxoimidazolidin-4-one (2) as synthons. Aromatic aldehydes on condensation with 1 and 2 gave 2-arylidene-5,5-dimethylcyclohexane-1,3-dione (3) and 5-arylidene-3-[(4-chlorobenzylidene)amino]-2-thioxoimidazolidin-4-one (4), respectively. Compounds 3 and 4 were forced to undergo heterocyclization reaction with nucleophilic reagents to give the title compounds. The newly synthesized heterocyles (5–8) were characterized based on their chemical properties and spectroscopic data, and were found to inhibit Staphylococcus aureus and Corynebacterium diphtheriae.
ISSN:0352-5139
DOI:10.2298/JSC0911219D