Catalyst- and Base-free One-pot, Multicomponent, De Novo Assembly of Structurally Diverse Morpholine Glycoconjugates

Abstract

A catalyst-, metal- and base-free unprecedented one-pot multicomponent synthetic strategy has been established for the construction of various substituted morpholine glycoconjugates through four-component reactions of glycosyl amino alcohol, chloroacetone, acid, and isocyanides. Unexpectedly, this one-pot approach generates only the cyclized morpholine scaffolds rather than normal Ugi adduct without any external base. This reaction proceeds via in situ formations of Schiff-base followed by an intramolecular halogen displacement process, finally the Joullie-Ugi reaction takes place leading to the corresponding products with a mixture of diastereomers.

Keywords: Glycoconjugates; Morpholine; Multi-component reaction; One-pot; Ugi reaction.