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Molecules 2017, 22(11), 1924; doi:10.3390/molecules22111924

An Optimized Synthesis, Molecular Structure and Characterization of Benzylic Derivatives of 1,2,4-Triazin-3,5(2H,4H)-dione

1
Department of Medicinal and Applied Chemistry, College of Life Sciences, Kaohsiung Medical University, Kaohsiung 807, Taiwan
2
Department of Medical Research, Kaohsiung Medical University Hospital, Kaohsiung 807, Taiwan
3
Instrumentation Center, College of Science, National Taiwan University, Taipei 106, Taiwan
*
Author to whom correspondence should be addressed.
Received: 21 September 2017 / Accepted: 3 November 2017 / Published: 8 November 2017
(This article belongs to the Section Organic Synthesis)
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Abstract

4-Benzyl-1,2,4-triazin-3,5(2H,4H)-dione (3-benzyl-6-azauracil, 2), and 2,4-dibenzyl-1,2,4-triazin-3,5(2H,4H)-dione (1,3-dibenzyl-6-azauracil, 3) were synthesized by the reaction of 1,2,4-triazin-3,5(2H,4H)-dione (6-azauracil, 1) with benzyl bromide and potassium carbonate in dry acetone via the 18-crown-6-ether catalysis. In these reaction methods, we developed more convenient and efficient methodologies to afford compounds 2 and 3 in good yields. These compounds were characterized by 1H- and 13C-NMR, MS spectrum, IR spectroscopy and elemental analysis. The structure of 2 was verified by 2D-NMR measurements, including gHSQC and gHMBC measurements. A single-crystal X-ray diffraction experiment indicated that compound 3, with the molecular formula C17H15N3O2, crystallized from a CH3OH/CH2Cl2 diffusion solvent system in a monoclinic space group P21/c with a = 13.7844(13), b = 8.5691(8), c = 13.0527(12) Å, β = 105.961(2)°, V = 1482.3(2) Å3, Z = 4, resulting in a density Dcalc of 1.314 g/cm3. The crystal structure of compound 3 is tightly stabilized by contact with five other molecules from the six short contacts formed by intermolecular C−O···H−Car, C−H···Car, and weakly π···π stacking interactions. The dihedral angle 31.90° is formed by the mean planes of the benzene rings of the N-2 and N-4 benzyl groups. View Full-Text
Keywords: 1,2,4-triazine; 1,2,4-triazin-3,5(2H,4H)-dione; 6-azauracil; X-ray crystal structure; short contacts; synthesis 1,2,4-triazine; 1,2,4-triazin-3,5(2H,4H)-dione; 6-azauracil; X-ray crystal structure; short contacts; synthesis
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MDPI and ACS Style

Hwang, L.-C.; Yang, S.-Y.; Chuang, C.-L.; Lee, G.-H. An Optimized Synthesis, Molecular Structure and Characterization of Benzylic Derivatives of 1,2,4-Triazin-3,5(2H,4H)-dione. Molecules 2017, 22, 1924.

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