Synthesis of Some New Functionalized Bis-thiazolidin-5-one and Bis-thiazolidin-4-one Derivatives

A series of bis-thiazolidin-5-one and bis-thiazolidin-4-one derivatives 3and5 was prepared by the treatment of highly functional thiocarbamoyl intermediates 2 and 4 with chloroacetyl chloride and chloroacetic acid, respectively. Treatment of the bis-thiocarbamoyl derivative 4a with diazotized sulphanilic acid affected acetyl cleavage to afford the corresponding arylhydrazono-thiocarbamoyl derivative 6.The title compounds bis-thiazolidin-5-one and bis-thiazolidin-4-one derivatives showed high reactivity towards azo coupling reaction with diazotized sulphanilic acid and Knoevenagel reaction with 4-isopropylbenzaldehyde.