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


BAYRAK H. , DEMİRBAŞ A. , DEMİRBAŞ N. , Karaoglu S. A.

EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, vol.45, no.11, pp.4726-4732, 2010 (Journal Indexed in SCI) identifier identifier identifier

  • Publication Type: Article / Article
  • Volume: 45 Issue: 11
  • Publication Date: 2010
  • Doi Number: 10.1016/j.ejmech.2010.07.018
  • Title of Journal : EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY
  • Page Numbers: pp.4726-4732

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 CS2 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.