α-CYANOTHIOACETAMIDE IN HETEROCYCLIC SYNTHESIS: A NEW APPROACH FOR THE SYNTHESIS OF 4-OXO-4,5-DIHYDRO-1,3- THIAZOLE-2-THIOACETAMIDE DERIVATIVES

Abstract Treatment of α-cyanothioacetamide (1) with thioglycolic acid in pyridine led to the formation of 4-oxo-4,5-dihydro-l,3-thiazole-2-thioacetamide (2).(2) reacted with two equivalents of aryldiazoniurn chloride to afford the diarylazo derivatives (3a-c). However when (2) was reacted with an equivalent amount of aryldiazonium chloride the monoarylazo derivatives (4a-c) were obtained and not (5a-c), which can be prepared via the reaction of thioglycolic acid with α-arylazo-α-cyano-thioacetamide (6a-c). With aromatic aldehydes (2) reacted to give the diyildene derivatives (7a-d). The structures of the isolated products were established by elemental analyses, and spectral data studies.