Three 1,2,4-triazole derivatives containing subtituted benzyl and benzylamino groups

Abstract

The title compounds, 4-benzylamino-3-(4-methylbenzyl)-1-H1,2,4-triazol-5 (4M-one, C17H18N4O, (I), 3-(4-methylbenzyl)4- (4-methylbenzylamino) -1H-1,2,4-triazol-5 (4H) -one, C18H20N4O, (II), and 3-(4-chlorobenzyl)-4-(4-methylbenzylamino)-1H-1,2,4-triazol-5 (4H) -one, C17H17ClN4O, (III), were obtained from the corresponding Schiff base in the presence of diglyme and NaBH4. Each compound contains a 1,2,4-triazole ring and two benzene rings, which are essentially planar. The molecules are linked by a combination of intermolecular NH...O and N-H...N hydrogen bonds. Additionally, there is a weak pi-pi stacking interaction in (I), involving the benzene ring of the aminobenzyl group and the partially aromatic 1,2,4-triazole moiety, with a centroid-centroid distance of 3.7397 (10) Angstrom.