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Molecules 2006, 11(6), 444-452; doi:10.3390/11060444
Article

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
,
1, 1, 2
 and
3
1 Faculty of Medicinal and Applied Chemistry, Kaohsiung Medical University, Kaohsiung City 80708, Taiwan, ROC 2 Department of Psychiatry, Longcyuan Veterans Hospital, Pingtung 912, Taiwan 3 Instrumentation Center, College of Science, National Taiwan University, Taipei City 106, Taiwan
* Author to whom correspondence should be addressed.
Received: 31 May 2006 / Revised: 17 June 2006 / Accepted: 19 June 2006 / Published: 22 June 2006
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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 reactionof 6-amino-3-methyl-1,2,4-triazolo[3,4-f][1,2,4]triazin-8(7H)-one (1) with potassiumcarbonate and allyl bromide in dry acetone. The structures of these two derivatives wereverified by 2D-NMR measurements, including gHSQC and gHMBC measurements. Theminor compound 2 may possess aromatic character. A single crystal X-ray diffractionexperiment indicated that the major compound 3 crystallizes from dimethyl sulfoxide in themonoclinic space group P21/n and its molecular structure includes an attached dimethylsulfoxide molecule, resulting in the molecular formula C10H16N6O2S. Molecular structuresof 3 are linked by extensive intermolecular N-H···N hydrogen bonding [graph set C 1 (7)]. 1Each molecule is attached to the dimethyl sulfoxide oxygen via N-H···O intermolecularhydrogen bonding. The structure is further stabilized by π-π stacking interactions.
Keywords: 1; 2; 4-Triazine; 1; 2; 4-triazolo[3; 4-f][1; 2; 4]triazine; aromatic molecule; X-ray crystal structure; hydrogen bonds. 1; 2; 4-Triazine; 1; 2; 4-triazolo[3; 4-f][1; 2; 4]triazine; aromatic molecule; X-ray crystal structure; hydrogen bonds.
This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

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Hwang, L.-C.; Jane, S.-Y.; Lai, H.-Y.; Tu, C.-H.; Lee, G.-H. 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 2006, 11, 444-452.

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