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.
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.
Hwang
Long-Chih
LC
Faculty of Medicinal and Applied Chemistry, Kaohsiung Medical University, Kaohsiung City 80708, Taiwan, ROC. lnchhw@kmu.edu.tw
Jane
Shin-Yi
SY
Lai
Hsing-Yi
HY
Tu
Chun-Hsien
CH
Lee
Gene-Hsiang
GH
D018360:Crystallography, X-Ray; D006841:Hydrocarbons, Aromatic / Q000737:chemistry; D006860:Hydrogen Bonding; D009682:Magnetic Resonance Spectroscopy; D008958:Models, Molecular; D017550:Spectroscopy, Fourier Transform Infrared; D014227:Triazines / Q000737:chemistry*; D014230:Triazoles / Q000138:chemical synthesis* / Q000737:chemistry*
D006841:Hydrocarbons, Aromatic; D014227:Triazines; D014230:Triazoles; C093444:1,2,4-triazine