SYNTHESIS AND REACTIONS OF SOME THIENO[2,3-d]PYRIMIDINE DERIVATIVES

Abstract

Abstract 5-Cyano-4-oxo-6-phenyl-2-thioxo-1,2,3,4-tetrahydropyrimidine (I) reacts with P2S5 in pyridine to give pyrimidine-2,4-dithione (II). Further reaction of II with ethyl chloroacetate, chloroacetanilide, phenacyl bromide, bromoacetone and chloroacetonitrile gave the corresponding thieno[2,3-d]pyrimidine derivatives (III-VI). Interaction of compound IVa with hydrazine hydrate in ethanol or diluted ethanol gave the hydrazide and hydrazino derivatives (VII, IX), which reacted with aromatic aldehydes to give the corresponding hydrazones (VIIIa-c, Xa-c ). Alkaline hydrolysis of IV, using KOH gave the acid XI with extrusion of thioglycolic acid. Key Words: PyrimidinedithioneThienopyrimidinebactericidal activity.