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


Uygun Y., BAYRAK H. , Ozkan H.

TURKISH JOURNAL OF CHEMISTRY, cilt.37, sa.5, ss.812-823, 2013 (SCI İndekslerine Giren Dergi) identifier identifier

  • Yayın Türü: Makale / Tam Makale
  • Cilt numarası: 37 Konu: 5
  • Basım Tarihi: 2013
  • Doi Numarası: 10.3906/kim-1212-66
  • Dergi Adı: TURKISH JOURNAL OF CHEMISTRY
  • Sayfa Sayıları: ss.812-823

Özet

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.