Synthesis of quinoxaline 1,4-di-N-oxide analogues and crystal structure of 2-carbomethoxy-3-hydroxyquinoxaline-di-N-oxide

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) ?, b = 10.7514 (9) ?, c = 13.2728 (11) ?, V = 1958.5 (3) ? 3, Z = 8. The X-ray crystallographic analysis reveals that quinoxaline 1,4-di-N-oxide displays acyloin-endiol tautomerism.