Glycosides of N-hydroxy-N-arylamine derivatives. Part 2. Convenient synthetic methods for N-glycosides of N-hydroxy-N-arylamines

Abstract

Two convenient methods for the synthesis of N-glucuronides of N-hydroxy-N-arylamines, (8a–e) and (9a), have been developed. N-Hydroxy-N-arylamines (6a–e) were condensed with triethylammonium O-glucopyranuronate (4) to give 1 -deoxy-1 -(N-hydroxy-N-arylamino)-β-D-glucopyranuronates (8a–e)(method A), and with D-glucofuranurono-6,3-lactone (12) to give 1-deoxy-1-(N-hydroxy-N-arylamino)-D-glucofuranurono-6,3-lactones (14a–e), which were also converted into the same pyranuronates as obtained by method A (method B). Pyridinium perchlorate in pyridine was a particularly effective acid catalyst in these condensation reactions, and also the N-glucoside (11e) was synthesized from D-glucose under the same conditions as those of method A. The mechanism of formation of compounds (14a–e) and (8a–e), and the ring transformation of compounds (14a–e) into compounds (8a–e), are briefly discussed.