Aspects on the Mechanism of the 1-Phenyl-1H-pyrazolo[3,4-b]quinoxaline Formation

Mohamed A. Mostafa, Salah L. Aboulela, Mohammed A. E. Sallam, Farida F. Louis, Thorleif Anthonsen

Department of Chemistry, Faculty of Science, Alexandria University, Ibrahimia, Egypt.
Department of Chemistry, Norwegian University of Science and Technology, Trondheim, Norway.

DOI: 10.4236/gsc.2012.22012                

Abstract

Condensation of D-glucose, o-phenylenediamine and N,N-benzylphenylhydrazine hydrochloride (NNBPHH) in a one-pot reaction, or condensation of 2-(D-arabino-tetritol-1-yl) quinoxaline and NNBPHH, gave 3-(D-erythro-glycerol-1- yl)-1-phenyl-1H-pyrazolo[3,4-b]quinoxaline. The structure of the latter was determined by 1H NMR spectroscopy and by synthesis using phenylhydrazine hydrochloride instead of NNBPHH. Condensation of D-glucose and 4,5-dichloro-o-phenylenediamine gave 6,7-dichloro-2-(D-arabino-tetritol-1-yl)quinoxaline, which upon condensation with NNBPHH gave the corresponding 6,7-dichloro-3-(D-erythro-glycerol-1-yl)-1-phenyl-1H-pyrazolo[3,4-b]quinoxaline. The structure and mechanism of formation of these compounds are discussed.

Keywords

2-(D-arabino-tetritol-1-yl)quinoxaline; Pyrazolo[3, 4-b]quinoxalines; 3-(D-erythro-glycerol-1-yl)-1-phenyl-1H-pyrazolo-[3, 4-b]qunoxaline; 4, 5-Dichloro-o-phenylenediamine; 6, 7-Dichloro-2-(D-arabino-tetritol-1-yl)quinoxaline; 6, 7-Dichloro-3-(D-erythro-glycerol-1-yl)-1-phenyl-1H-pyrazolo-[3, 4-b]quinoxaline; N, N-Benzylphenylhydrazine hydrochloride

Conflicts of Interest

The authors declare no conflicts of interest.

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