Oxidative cyclization of N-alkyl-o-methyl-arenesulfonamides to biologically important saccharin derivatives |
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Authors: | Liang Xu |
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Affiliation: | Department of Chemistry, University of New Orleans, New Orleans, LA 70148, USA |
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Abstract: | Various biologically important saccharin skeletons and their N-alkyl derivatives have been efficiently prepared by chromium(VI) oxide catalyzed H5IO6 oxidation of N-alkyl-o-methyl-arenesulfonamides in acetonitrile. N-tert-Butyl saccharin skeletons were easily prepared by H5IO6-CrO3 oxidation of N-tert-butyl-o-methyl arenesulfonamides in the presence of acetic anhydride. The method that furnished the novel fluoro and trifluoromethyl substituted saccharin skeletons is characterized by two steps, a simple work-up procedure, a single purification and good overall yields from substituted toluene derivatives. |
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Keywords: | Saccharin Sulfonamides Periodic acid Chromium trioxide Oxidation Oxidative cyclization |
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