Synthesis and characterization of new trihetero cyclic compounds consisting of 1,2,4-triazol-3-one, 1,3,4-thiadiazole and 1,3,4-oxadiazole rings


Demirbas N.

TURKISH JOURNAL OF CHEMISTRY, vol.29, no.2, pp.125-133, 2005 (Journal Indexed in SCI) identifier

  • Publication Type: Article / Article
  • Volume: 29 Issue: 2
  • Publication Date: 2005
  • Title of Journal : TURKISH JOURNAL OF CHEMISTRY
  • Page Numbers: pp.125-133

Abstract

A series of acetic acid derivatives (2a-c) was synthesized by the condensation of compounds la-c with chloroacetic acid. The treatment of carboxylic acid derivatives with thiosemicarbazide in phosphorus oxychloride and subsequent diazotation of the products (3a-c) afforded 5-alkyl-2-[(5-chloro-1,3,4-thiadiazol-2-yl)methyl]-2,4-dihydro-3H-1,2,4-triazol-3-one derivatives (4a-c). The treatment of compounds 4a-c with thiourea produced 5-alkyl-2-[(5-mercapto-1,3,4-thiadiazol-2-yl)methyl]-2,4-dihydro-3H-1,2,4-triazol-3-one derivatives (5a-c). Subsequently, compounds 5a-c were converted to acid hydrazides by treatment with hydrazine hydrate after esterification (7a-e). Moreover, the reaction of compounds 7a-c with carbon disulfite in the presence of KOH afforded 5-alkyl-2-[(5-{[(5-mercapto-1,3,4-oxadiazol-2-yl)methyl]thio}-1,3,4-thiadiazol-2-yl)methyl]-2,4-dihydro-3H-1,2,4-triazol-3-ones (8a-c).