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, cilt.29, sa.2, ss.125-133, 2005 (SCI-Expanded) identifier

  • Yayın Türü: Makale / Tam Makale
  • Cilt numarası: 29 Sayı: 2
  • Basım Tarihi: 2005
  • Dergi Adı: TURKISH JOURNAL OF CHEMISTRY
  • Derginin Tarandığı İndeksler: Science Citation Index Expanded (SCI-EXPANDED), Scopus, TR DİZİN (ULAKBİM)
  • Sayfa Sayıları: ss.125-133
  • Karadeniz Teknik Üniversitesi Adresli: Evet

Özet

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).