Condensation of 2-acetyl-5-bromobenzofuran with hydrazine derivatives 2a,b afforded hydrazone derivatives 3a,b, which reacted with alkyl halides4a,b to yield ethylidene derivatives 5a,b. Also, 3a reacted with hydrazonyl halides6a,b to give 1,3,4-thiadiazole derivatives 9a,b. Thiosemicarbazone3b was reacted with acetic anhydride and halogenated compounds to afford the corresponding heterocyclic derivatives 10, 11a,b, 12-17 and 18a,b.Moreover, interaction of 16 with tetracyanoethylene and salicyldehyde derivatives furnished 24 and 26a,b, respectively. Finally, reaction of 16 with DMF-DMA afforded enaminone29, which on treatment with different heterocyclic amines yielded 31 and 33 respectively. Some of the newly synthesized compounds showed promising antimicrobial activity.

benzofuran, 1, 3, 4-thiadiazole, thiazolidinone, thiazole, antimicrobial