Synthesis, molecular structure and characterization of allylic derivatives of 6-amino-3-methyl-1,2,4-triazolo[3,4-f][1,2,4]-triazin-8(7H)-one

Abstract

1-Allyl- (2) and 7-allyl-6-amino-3-methyl-1,2,4-triazolo[3,4-f][1,2,4] triazin-8(7H)-one (3) were obtained via the 18-crown-6-ether catalyzed room temperature reaction of 6-amino-3-methyl-1,2,4-triazolo[3,4-f][1,2,4]triazin- 8(7H)-one (1) with potassium carbonate and allyl bromide in dry acetone. The structures of these two derivatives were verified by 2D-NMR measurements, including gHSQC and gHMBC measurements. The minor compound 2 may possess aromatic character. A single crystal X-ray diffraction experiment indicated that the major compound 3 crystallizes from dimethyl sulfoxide in the monoclinic space group P21/n and its molecular structure includes an attached dimethyl sulfoxide molecule, resulting in the molecular formula C 10H16N6O2S. Molecular structures of 3 are linked by extensive intermolecular N-H⋯N hydrogen bonding [graph set C11(7)]. Each molecule is attached to the dimethyl sulfoxide oxygen via N-H⋯O intermolecular hydrogen bonding. The structure is further stabilized by π-π stacking interactions. © 2006 by MDPI.