Microwave-assisted 1,3-dipolar cycloaddition reactions of vinylic glycosides with aryl azides - Unexpected synthesis of triazoles and acetyl group migration

Abstract

The synthesis of sugar-derived triazolines was attempted under microwave irradiation, by 1,3-dipolar cycloaddition to azides. However, due to the "push-pull" nature of the dipolarophile, we have obtained triazoles by elimination of the sugar unit, which then has one free hydroxyl group at a selective carbon position. The triazoles obtained are important precursors of anticonvulsive drugs. Furthermore, we have observed that under microwave irradiation of 300W it is possible to promote acetyl group migration to a free hydroxyl group within the carbohydrate moiety. © ARKAT USA, Inc.