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Aspects on the Mechanism of the 1-Phenyl-1<i>H</i>-pyrazolo[3,4-<i>b</i>]quinoxaline Formation
Department of Chemistry, Faculty of Science, Alexandria University, Ibrahimia, Egypt
Department of Chemistry, Faculty of Science, Alexandria University, Ibrahimia, Egypt
Department of Chemistry, Faculty of Science, Alexandria University, Ibrahimia, Egypt
Department of Chemistry, Faculty of Science, Alexandria University, Ibrahimia, Egypt
Department of Chemistry, Norwegian University of Science and Technology, Trondheim, Norway
- 1 Department of Chemistry, Faculty of Science, Alexandria University, Ibrahimia, Egypt
- 2 Department of Chemistry, Faculty of Science, Alexandria University, Ibrahimia, Egypt
- 3 Department of Chemistry, Faculty of Science, Alexandria University, Ibrahimia, Egypt
- 4 Department of Chemistry, Faculty of Science, Alexandria University, Ibrahimia, Egypt
- 5 Department of Chemistry, Norwegian University of Science and Technology, Trondheim, Norway
Green and Sustainable Chemistry·Volume 02 (2012)·Pages 71–75·Published 11 May 2012·DOI10.4236/gsc.2012.22012
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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.
Keywords2-(D-<i>arabino</i>-tetritol-1-yl)quinoxalinePyrazolo[34-b]quinoxalines3-(D-<i>erythro</i>-glycerol-1-yl)-1-phenyl-1H-pyrazolo-[34-b]qunoxaline45-Dichloro-o-phenylenediamine67-Dichloro-2-(D-<i>
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