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

• Published in: Molecules (Basel, Switzerland) Vol. 11; no. 6; pp. 444 - 452
• Main Authors: Hwang, Long-Chih, Jane, Shin-Yi, Lai, Hsing-Yi, Tu, Chun-Hsien, Lee, Gene-Hsiang
• Format: Journal Article
• Language: English
• Published: Switzerland MDPI AG 22.06.2006; MDPI
• Subjects: 4-f; 4-Triazine; 4-triazolo; aromatic molecule; Carbon; Crystallography, X-Ray; Hydrocarbons, Aromatic - chemistry; Hydrogen; Hydrogen Bonding; hydrogen bonds; Magnetic Resonance Spectroscopy; Models, Molecular; Molecular structure; Potash; Potassium; Spectroscopy, Fourier Transform Infrared; Triazines - chemistry; Triazoles - chemical synthesis; Triazoles - chemistry; X-ray crystal structure; Taiwan
• ISSN: 1420-3049; 1420-3049
• DOI: 10.3390/11060444

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 P2(1)/n and its molecular structure includes an attached dimethylsulfoxide molecule, resulting in the molecular formula C(10)H(16)N(6)O(2)S. Molecular structures of 3 are linked by extensive intermolecular N-H...N hydrogen bonding [graph set C(1)(1)(7)]. 1 Each molecule is attached to the dimethyl sulfoxide oxygen via N-H...O intermolecular hydrogen bonding. The structure is further stabilized by pi-pi stacking interactions.