Three 1,2,4-Triazole Derivatives Containing Substituted Benzyl and Benzylamino Groups

Abstract

The title compounds, 4-benzylamino-3-(4-methylbenzyl)-1H-1,2,4-triazol- 5(4H)-one, C<inf>17</inf>H<inf>18</inf>N<inf>4</inf>O, (I), 3-(4-methylbenzyl)- 4-(4-methylbenzylamino)-1H-1,2,4-triazol-5(4H)-one, C<inf>18</inf>H <inf>20</inf>-N<inf>4</inf>O, (II), and 3-(4-chlorobenzyl)-4-(4- methylbenzylamino)-1H/-l,2,4-triazol-5(4H)-one, C<inf>17</inf>H <inf>17</inf>ClN<inf>4</inf>O, (III), were obtained from the corresponding Schiff base in the presence of diglyme and NaBH<inf>4</inf>. 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 N-H⋯O and N-H⋯N hydrogen bonds. Additionally, there is a weak π-πn 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) Å. © 2005 International Union of Crystallography.