Cyclization of some carbothioamide derivatives containing antipyrine and triazole moieties and investigation of their antimicrobial activities

Abstract

Acetohydrazide derivative containing both antipyrine and triazole nuclei ( 5) was obtained starting from ethyl hydrazinecarboxylate derivative ( 2) and 4-aminoantipyrine ( 1) by three steps. The treatment of compound 5 with CS 2 afforded the conversion of hydrazide function into 5-mercapto-1,3,4-oxadiazole ring leading to the formation of 7. Then, 7 gave the product containing triazolotriazine moiety ( 9) by the reaction with hydrazine hydrate. The synthesis of the compounds incorporating the 1,3,4-thiadiazole ( 10a– c), 1,2,4-triazole ( 11a– c) or 1,3-thiazole ( 12, 13) nucleus as third heterocycle was performed by the acidic or basic treatment of compounds 6a– c which were obtained from the reaction of 5 with several isothiocyanates, or by the condensation of 6a with two different phenacyl bromides, respectively. The antimicrobial activity study revealed that all the compounds showed good activities except 3– 5.