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


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.

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M. A. Mostafa, S. L. Aboulela, M. A. E. Sallam, F. F. Louis and T. Anthonsen, "Aspects on the Mechanism of the 1-Phenyl-1H-pyrazolo[3,4-b]quinoxaline Formation," Green and Sustainable Chemistry, Vol. 2 No. 2, 2012, pp. 71-75. doi: 10.4236/gsc.2012.22012.

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The authors declare no conflicts of interest.


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