Synthesis and biological activities of methylenebis-4H-1,2,4-triazole derivatives

Uygun Y., BAYRAK H., Ozkan H.

TURKISH JOURNAL OF CHEMISTRY, vol.37, no.5, pp.812-823, 2013 (SCI-Expanded) identifier identifier

  • Publication Type: Article / Article
  • Volume: 37 Issue: 5
  • Publication Date: 2013
  • Doi Number: 10.3906/kim-1212-66
  • Journal Indexes: Science Citation Index Expanded (SCI-EXPANDED), Scopus, TR DİZİN (ULAKBİM)
  • Page Numbers: pp.812-823
  • Keywords: 1,2,4-Triazole, morpholine, furan, Schi ff base, Mannich base, antimicrobial activity, ANTIMICROBIAL ACTIVITIES, ANTIBACTERIAL, AGENTS, ACID
  • Karadeniz Technical University Affiliated: Yes


5,5'-Methylenebis(4-phenyl-4 H -1,2,4-triazole-3-thiol) (2) was synthesized starting from hydrazinecarbothioamide compound (1). Treatment of compound 2 with ethyl bromoacetate produced diethyl 5,5'-{methylenebis[(4-phenyl-4H-1,2,4-triazole-5,3-diyl)thio]}diacetate (3), which was converted to the corresponding diacetohydrazide derivative (4) by treatment with hydrazine hydrate. The reaction of compound 4 with several aldehydes produced the corresponding arylidene hydrazides, 5a-d. Syntheses of Mannich bases 6a-c were carried out by the treatment of compound 2 with several amines in the presence of formaldehyde. (4{[5-({5-[(4-Amino-2-chlorophenyl)thio]-4-phenyl-4H -1,2,4-triazol- 3-yl}methyl)-4-phenyl-4H-1,2,4-triazol-3-yl]thio}-3-chlorophenyl)amine (8) was prepared by reduction of 2 nitro groups of 3,3 ' -methylenebis {5-[(2-chloro-4-nitrophenyl)thio]-4-phenyl-4H-1,2,4-triazole} (7) that were obtained from the condensation of 2 with 3,4-dichloronitrobenzene.