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Molecules 2011, 16(8), 6894-6901; doi:10.3390/molecules16086894

Synthesis of Quinoxaline 1,4-di-N-Oxide Analogues and Crystal Structure of 2-Carbomethoxy-3-hydroxyquinoxaline-di-N-oxide

College of Chemical and Environmental Engineering, Shanghai Institute of Technology, Shanghai 200235, China
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Received: 28 June 2011 / Revised: 3 August 2011 / Accepted: 8 August 2011 / Published: 12 August 2011
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Abstract

A series of quinoxaline 1,4-di-N-oxide analogues were prepared from benzofurazan N-oxide derivatives and β-diketone ester compounds by the improved Beirut reaction. The structures of the target products were characterized by NMR, MS, IR and elemental analysis measurements, and that of 2-carbomethoxy-3-hydroxyquinoxaline- di-N-oxide was further confirmed by single-crystal X-ray diffraction. Its crystal structure belongs to the monoclinic system, space group C2/c with a = 14.4320 (12) Å, b = 10.7514 (9) Å, c = 13.2728 (11) Å, V = 1958.5 (3) Å 3, Z = 8. The X-ray crystallographic analysis reveals that quinoxaline 1,4-di-N-oxide displays acyloin-endiol tautomerism.
Keywords: quinoxaline 1,4-di-N-oxide; Beirut reaction; acyloin-endiol tautomerism quinoxaline 1,4-di-N-oxide; Beirut reaction; acyloin-endiol tautomerism
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Xu, Y.; Wu, F.; Yao, Z.; Zhang, M.; Jiang, S. Synthesis of Quinoxaline 1,4-di-N-Oxide Analogues and Crystal Structure of 2-Carbomethoxy-3-hydroxyquinoxaline-di-N-oxide. Molecules 2011, 16, 6894-6901.

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