Metal free synthesis of morpholine fused [5,1-c] triazolyl glycoconjugates via glycosyl azido alcohols

Abstract

A series of diverse glycosyl 1,2-azido alcohols, obtained from readily available carbohydrates, were converted to structurally varied rare and novel sugar derived morpholine fused [5,1-c]-triazoles via a one-pot strategy. After incorporating a propargyl functionality at the hydroxyl group of the sugar derived 1,2-azido alcohols, the resulting in situ generated azido–alkyne affords numerous C- and O-glycosyl bicyclic ring systems with medicinal value via a metal free cycloaddition reaction. The structures of all the developed molecules have been elucidated using ¹H NMR, ¹³C NMR, IR and MS spectroscopy.