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Synthesis and antimicrobial studies of 4-oxo-thiazolidine derivatives

Authors: Hitesh D. Patel; B. D. Mistry; K. R. Desai;

Synthesis and antimicrobial studies of 4-oxo-thiazolidine derivatives

Abstract

Chemistry Department, Gujarat University, Ahmedabad-380 009, Gujarat, India Chemistry Department, B. K. M. Science College, Valsad-396 001, Gujarat, India Chemistry Department, South Gujarat University, Surat-395 007, Gujarat, India E-mail : hiteshl3chem@rediffmail.com Manuscript received 12 March 2008, revised 20 October 2008, accepted 12 November 2008 Ethyl (4-chlorophenoxy)acetate (1) upon condensation with hydrazine hydrate gave 2-(4-chlorophenoxy)- acetohydrazide (2) which by condensation with aromatic aldehydes gave 2-(4-chlorophenoxy)-N-(substitutedbenzylidene) acetohydrazide (3a-k). Derivatives (3a-k) fused with thioglycolic acid and thiolactic acid gave 4-thiazolidinone derivatives (4a-k) and 5-methyl-4-thiazolidinone derivatives (5a-k) respectively. 4-Thiazolidinone derivatives (4a-k) treated with formaldehyde and p-nuoroaniline gave 2-( 4-chlorophenoxy)-N-{2-(substitutedphenyl)-5-[(4-nuoropheny l)aminomethyl]-4-oxo-1,3- thiazolidine-3-yl}acetamide (6a-k). The structures of the synthesized compounds were assigned on the basis of IR, 1H NMR, LC-MS and elemental analysis data.

Keywords

thiazolodinones, antimicrobial activity, Mannich reaction, Schiff base's derivatives, microwave method, Cycloaddition

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