Catalyst‐ and Base‐free One‐pot, Multicomponent, De Novo Assembly of Structurally Diverse Morpholine Glycoconjugates. Issue 23 (21st October 2022)

• Record Type: Journal Article
• Authors: Khanam, Ariza; Lal, Mohan; Mandal, Pintu Kumar
• Is Part Of: Chemistry, an Asian journal. Volume 17:Issue 23(2022)
• Page Start: n/a
• Page End: n/a
• Publication Date: 2022-10-21
• Subjects: Glycoconjugates -- Morpholine -- Multi-component reaction -- One-pot -- Ugi reaction; Chemistry -- Periodicals; 540.5
• DOI: 10.1002/asia.202200849
• Languages: English
• ISSNs: 1861-4728

Abstract

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. Abstract : An unprecedented synthesis of diversely substituted morpholine glycoconjugates enabled by one‐pot multicomponent reaction of glycosyl amino alcohol, chloroacetone, acid, and isocyanides under catalyst, metal and base‐free condition.The highlights of the present strategy comprise of the formation of only cyclized morpholine scaffolds in place of normal Ugi adduct, in absence of external base.