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

Abstract

This paper presents new heterocyclic compounds from the class of 1,2,4-triazole-3(4H)-thione which were obtained by intramolecular cyclization, in basic media of the some acylthiosemicarbazides containing diphenylsulfone moieties. The new 1-(4-(4-X-phenylsulfonyl)benzoyl)-4- (4-iodophenyl)-thiosemicarbazides (7a-c) were obtained by the reaction of 4-(4-X-phenylsulfonyl)-benzoic acid hydrazides (6a-c) (X=H, Cl or Br) with 4-iodophenylisothiocyanate. 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-phenylsulfonyl)phenyl)-4-(4-iodophenyl)-2H-1,2,4-triazole-3(4H)-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.

Keywords

• 1-acylthiosemicarbazide
• intramolecular cyclization
• 1,2,4-triazole-3(4H)-thione