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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 (CC BY 3.0).
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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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