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

Molecules

Long-Chih Hwang¹  Shin-Yi Jane¹  Hsing-Yi Lai¹  Chun-Hsien Tu² 

[1] Faculty of Medicinal and Applied Chemistry, Kaohsiung Medical University, Kaohsiung City 80708, Taiwan, ROC;Department of Psychiatry, Longcyuan Veterans Hospital, Pingtung 912, Taiwan, ROC

关键词: 1;    2;    4-Triazine;    1;    2;    4-triazolo[3;    4-f][1;    2;    4]triazine;    aromatic molecule;    X-ray crystal structure;    hydrogen bonds;   

DOI  :  10.3390/11060444

来源: mdpi

【 摘 要 】

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 C₁₀H₁₆N₆O₂S. Molecular structures of 3 are linked by extensive intermolecular N-H···N hydrogen bonding [graph set (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.

【 授权许可】

Unknown   
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