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

Aspects on the Mechanism of the 1-Phenyl-1<i>H</i>-pyrazolo[3,4-<i>b</i>]quinoxaline Formation
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摘要 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. 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.
出处 《Green and Sustainable Chemistry》 2012年第2期71-75,共5页 绿色与可持续化学(英文)
关键词 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 7-Dichloro-3-(D-erythro-glycerol-1-yl)-1-phenyl-1H-pyrazolo-[3 4-b]quinoxaline N N-Benzylphenylhydrazine hydrochloride 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 7-Dichloro-3-(D-erythro-glycerol-1-yl)-1-phenyl-1H-pyrazolo-[3 4-b]quinoxaline N N-Benzylphenylhydrazine hydrochloride
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