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Paper | Regular issue | Vol 36, No. 4, 1993, pp.833-844
Published online, 1st January, 1970
DOI: 10.3987/COM-92-6244
Synthesis of Pyrazole C-Glycosides by 1,3-Dipolar Cycloaddition of Nitrilimines Formed by Lead Tetraacetate Oxidation of p-Nitrophenylhydrazones of Aldehydo Sugars

Jean M. J. Tronchet,* Jeannine F. Tronchet, and Françoise Barbalat-Rey

*Institute of Pharmaceutical Chemistry, University of Geneva, 30, Quai e.-Ansermet, CH-1211 Geneva 4, Switzerland


Aldehydo sugars p-nitrophenylhydrazones upon treatment with lead tetraacetate in the presence of an excess of methyl acrylate afforded, besides N’-acetylhydrazide derivatives, methyl 3-glycosyl-1-p-nitrophenylpyrazoline-5-carboxylates which were readily oxidized to the corresponding pyrazoles. The methyl pyrazole-5-carboxylates were converted to 5-carboxamides.