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.

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Condensation of thiazolidin-5-one derivative 1 with different aromatic aldehydes gave the corresponding arylidenes 2a-e. Compound 2e was reacted with urea and thiourea to give the corresponding thiazolo [5,4-d]pyrimidine derivatives 3a,b, respectively. Treatment of compound 1 with phenyl isothiocyanate in basic DMF gave the nonisolable potassium salt of the adduct 4, which underwent heterocyclization upon treatment with chloroacetyl chloride and phenacyl bromide to give the corresponding [2,4 ] bisthiazolidinylidenes 5 and 8. Moreover, the reactions of compound 1 with a variety of reagents, e.g., ninhydrin and isatin, were investigated. The structures of these compounds were established by analytical and spectral data.

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