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Molecules 2006, 11(2), 169-176; doi:10.3390/11020169

Synthesis and Molecular Structure of 6-Amino-3-benzylmercapto-1,2,4-triazolo[3,4-f][1,2,4]triazin-8(7H)-one

1,* , 2, 3 and 4
1 Faculty of Medicinal and Applied Chemistry, Kaohsiung Medical University, Kaohsiung City 80708, Taiwan 2 Department of Psychiatry, Longcyuan Veterans Hospital, Pingtung 912, Taiwan 3 Department of Pharmacy, Kaohsiung Veterans General Hospital, Kaohsiung City 807, Taiwan 4 nstrumentation Center, College of Science, National Taiwan University, Taipei City 106, Taiwan
* Author to whom correspondence should be addressed.
Received: 5 November 2005 / Revised: 10 March 2006 / Accepted: 10 March 2006 / Published: 17 March 2006
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The title compound 6-amino-3-benzylmercapto-1,2,4-triazolo[3,4-f][1,2,4]-triazin-8(7H)-one (4), molecular formula C11H10N6OS, was obtained by the reaction of3-amino-2-benzyl-6-hydrazino-1,2,4-triazin-5(2H)-one (3) with carbon disulfide in awater/pyridine mixture. Compound 4 can also be synthesized by reacting6-amino-3(2H)mercapto-1,2,4-triazolo[3,4-f][1,2,4]triazin-8(7H)-one (7) with benzylbromide in methanolic ammonia water. The compound crystallizes in the monoclinicspace group P21/c with a = 7.2926(15), b = 14.456(2), c = 11.436(2) å, β = 105.30(2)°, V= 1162.9(4) å3 and Z = 4, resulting in a density Dcalc of 1.567 g/cm3. Molecules of 4 arelinked by extensive intermolecular N-H···N and N-H···O hydrogen bonding [graph set R22 (9)]. The structure is further stabilized by π-π stacking interactions. 2
Keywords: 1; 2; 4-Triazine; 1; 2; 4-triazolo[3; 4-f][1; 2; 4]triazine; X-ray crystal structure; hydrogen bonds. 1; 2; 4-Triazine; 1; 2; 4-triazolo[3; 4-f][1; 2; 4]triazine; X-ray crystal structure; hydrogen bonds.
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Hwang, L.-C.; Tu, C.-H.; Wang, J.-H.; Lee, G.-H. Synthesis and Molecular Structure of 6-Amino-3-benzylmercapto-1,2,4-triazolo[3,4-f][1,2,4]triazin-8(7H)-one. Molecules 2006, 11, 169-176.

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