Synthesis and reactions of 2-cyano-2-(5-oxo-3-phenyl-thiazolidin-2-ylidene) -acetamides

Abstract

The base promoted nucleophilic addition of cyanoacetamide derivatives 2a,b to equimolar amount of phenyl isothiocyanate in DMF containing potassium hydroxide afforded the corresponding potassium sulfide salts 3a,b which were not isolated but which underwent heterocyclisation upon treatment with chloroacetyl chloride to give the corresponding 2-cyano-2-(5-oxo-3-phenylthiazolidin-2- ylidene)-acetamide derivatives 4a,b. The reactions of 4a,b with aryl diazonium salts, bromine and aromatic aldehydes were studied in order to obtain compounds 5-11.