Synthetic studies toward aryl-(4-aryl-4H-[1,2,4]triazole-3-yl)-amine from 1,3-Diarylthiourea as urea mimetics

A thiophile-promoted synthesis of disubstituted 4H-[1,2,4]triazole-3-yl-amines as urea mimetics from the corresponding 1,3-disubstituted thioureas is studied, and the scope and limitations of this reaction are presented. The electronic and steric effects of the substitution on the phenyl rings of the 1,3-diarylthioureas play an important role in the formation of the intermediary carbodimide the direction of the subsequent ring closure of the N-acyl hydrazide adduct.