Studies on N-Glycosides

Part 18. The Formation of Osone from the Molecular-rearrangement Product of N-Glucoside. (1)

Abstract

A new method which has been previously found by the authors to be satisfactory for the preparation of osone was further studied. N-p-tolyl-_D-isoglucosamine, the conversion product of p-toluidine-N-_D-glucoside by the molecular rearrangement named the AMADORI rearrangement, was subject to the treatment in the presence of hydrazine hydrate to form glucosone which was determined by means of the phenylosazone formed in 3 hours after the addition of phenylhydrazine to the reaction mixture at room temperature.
The conditions for the reaction have been worked out, and it has been shown that the osone is formed in not less than 57% of the theoretical yield under the best conditions.
The isolation of the reaction product was carried out, and this product posessed the characteristic properties of osone and formed a crystalline substance (quinoxaline) melting at 180° by reaction with o-phenylenediamine, thus proving itself to be glucosone.