TITLE:
Aspects on the Mechanism of the 1-Phenyl-1H-pyrazolo[3,4-b]quinoxaline Formation
AUTHORS:
Mohamed A. Mostafa, Salah L. Aboulela, Mohammed A. E. Sallam, Farida F. Louis, Thorleif Anthonsen
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
JOURNAL NAME:
Green and Sustainable Chemistry,
Vol.2 No.2,
May
11,
2012
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.