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

Abstract

The title compounds, 4-benzylamino-3-(4-methylbenzyl)-1H-1,2,4-triazol-5(4H)-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 NaBH(4). 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 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) A.

4-Ethyl-3-(2-thienylmethyl)-Δ2-1,2,4-triazoline-5-thione

“…This distance is also comparable to literature data (Yilmaz et al, 2005). The thiophene ring is disordered over two orientatians with respect to the C6-C7 bond; the dihedral angles between the triazole and the thiophene rings for the two orientations of the second one are 88.5 (7) and 85.7 (8)°.…”

“…For details of the synthesis, see: Wujec et al (2004Wujec et al ( , 2007. For related structures, see: Yilmaz et al (2005).…”

4-(2-Pyridylmethyleneamino)-3-(2-thienylmethyl)-1H-1,2,4-triazol-5(4H)-one

“…The C6 N1 bond is clearly a double bond, being much shorter than the other C-N bonds in the triazole ring. This distance is also comparable to literature data (Ç oruh et al, 2003;Yilmaz et al, 2005). The crystal structure features centrosymmetric dimers, formed by classical intermolecular N-HÁ Á ÁO hydrogen bonds, involving the amine functionality and the carbonyl of the triazole ring (Table 2).…”

1-(Benzoylmethyl)-4-(3,5-dimethyl-4H-1,2,4-triazol-4-yl)-3-(2-thienylmethyl)-1H-1,2,4-triazol-5(4H)-one

“…Bond distances, angles and torsion angle data for (I) ( Table 1) show good agreement with those reported previously (Allen, 2002;Yılmaz et al, 2005;Ocak et al, 2003;Wen et al, 2005;Ç oruh, Kahveci, Ş aşmaz, Ag ar, Kim & Erdö nmez, 2003). The shorter C1-N1, N5-C23 and N6-C22 bonds confirm their expected double-bond character.…”

“…The dihedral angles between rings A/B, A/C, A/D, B/C, B/D and C/D are 85,45(16), 78.81 (18), 77.90 (17), 34.2 (2), 28.8 (2) and 23.4 (2) Å , respectively. A non-planar orientation of two substituted triazole rings has been observed previously (Ocak et al, 2003;Zhu et al, 2000;Bruno et al, 2003;Yılmaz et al, 2004Yılmaz et al, , 2005). However, 1,2,4-triazole derivatives with two Nlinked triazole rings have been observed to be planar (Ç oruh, Ç oruh, Kahveci, Ş aşmaz, Ag ar, Kim & Erdö nmez, 2003).…”