Synthesis and characterization of some 1,2,4-triazole-3-thiones obtained from intramolecular cyclization of new 1-(4-(4-X-phenylsulfonyl)benzoyl)-4-(4- iodophenyl)-3-thiosemicarbazides

Abstract

This paper presents new heterocyclic compounds from the class of 1,2,4-triazole-3-thione which were obtained by intramolecular cyclization, in basic media of some acylthiosemicarbazides containing diphenyl sulfone moieties. The new 1-(4-(4-X-phenylsulfonyl)benzoyl)-4-(4-iodophenyl)-3-thiose- micarbazides (7a-c) were obtained by the reaction of 4-(4-X-phenylsulfonyl)- benzoic acid hydrazides (6a-c) (X = H, Cl or Br) with 4-iodophenylisothio- cyanate. The cyclization of the acylthiosemicarbazides 7a-c in the presence of an 8 % NaOH solution resulted in the formation of the new 5-(4-(4-X-phenyl- sulfonyl)phenyl)-4-(4-iodophenyl)-2,4-dihydro-3i/-1,2,4-triazole-3-thiones (8a- -c). The structures of the newly synthesized compounds were elucidated by spectral methods (IR, UV-Vis,1H-NMR, 13C-NMR and MS spectroscopy) and elemental analysis. 2010 Copyright (CC) SCS.