Preparation and some reactions of D-glucosyl derivatives of 2-thioxo-1,3,4-oxadiazoles and 2-thioxo-1,3,4-thiadiazoles and their 2-oxo analogues

Abstract

2-Thioxo-1,3,4-oxadiazoles (1a,b) and 2-thioxo-1,3,4-thiadiazoles (1c,d) reacted with tetra- O-acetyl-α- D-glucopyranosyl bromide in the presence of potassium hydroxide to yield thioglucosides (2a–d, respectively, in good yield) and N-glucosyl derivatives (3a–d, respectively, in poor yield). Oxidation of 2a–d with potassium permanganate yielded the corresponding sulphones (4a–d), whereas 3a–d yielded the corresponding 2-oxo derivatives (5a–d). The acetates 2a–d, 3a–d, and 5a–d were deacetylated with ammonia to give the parent D-glucosyl derivatives. The products were characterized by u.v. and i.r. spectroscopy.