Synthesis and antimicrobial studies of 4-oxo-thiazolidine derivatives

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.