Synthesis of thiazole, benzothiazole, oxadiazole, thiadiazole, triazole and thiazolidinone incorporated coumarins

Abstract

3-Bromoacetylcoumarin-(2)obtained by brominationof 3-acetylcoumarin (1)was condensed with2-amin0-4-phenylthiazole,2-aminothiazole,2-aminobenzothiazole, 2- amino-4-phenyloxadiazole, 2-aminothiadiazole, 3-aminotriazole to form the corresponding heteroaryl aminoacetylcoumarins (3a-f).The reaction of 2 withthiourea furnished 2-amino-4-(coumarinyl-3) thiazole (4) which further reacted with phenyli$othiocyanate forming the unsymmetrical thiourea (5). The thiourea on cyclocondensation withchloroacetic acid gave the thiazolidinone (6)which on further reaction with differen~aromaUcaldehydes resulted inthe formationofthe corresponding arylidene compounds (7). The structures of the products were confirmed from their analytical and spectraldata.