Synthesis of some new thiazolidin-5-one derivatives of pharmaceutical interest

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.