BIS-ISOTHIOCYANATES IN HETEROCYCLIC SYNTHESIS: SYNTHESIS OF BIS 4-THIAZOLIDINONES, BIS THIAZOLES, AND BIS 4-AMINO-THIAZOLE DERIVATIVES

Abstract

Bis 2-thioxo-4-thiazolidinones (5a,b) were achieved by cyclocondensation of bis-isothiocyanates (3a,b) with sulfanylacetic acid at reflux temperature. Compounds (5a-c) were exploited to synthesize the versatile hitherto unknown bis(2-thioxo-4-thiazolidinone) deriva-tives (8, 9, 11, 12 & 16) via its reaction with some electrophiles. Reaction of bis ammonium dithiocarbamate derivatives [2b, (2a,c)] with chloroacetone, 4-nitrophenacyl bromide and 3-(2-bromoacetyl)-2H-chromene-2-one gave the corresponding bis thiazoles [18, (23a,b), 24], respectively, whereas, reaction of 2a,b with chloroacetonitrile gives bis (4-aminothiazoles) 21a,b. The synthesized compounds were characterized by IR, 1HNMR and mass spectral studies.