Bicyclic Heterocycles from Levulinic Acid through a Fast and Operationally Simple Diversity‐Oriented Multicomponent Approach. Issue 39 (10th October 2018)

• Record Type: Journal Article
• Authors: Lambruschini, Chiara; Basso, Andrea; Moni, Lisa; Pinna, Alessandro; Riva, Renata; Banfi, Luca
• Is Part Of: European journal of organic chemistry. Issue 39(2018)
• Page Start: 5445
• Page End: 5455
• Publication Date: 2018-10-10
• Subjects: Multicomponent reactions -- Nucleophilic substitution -- Isocyanides -- Renewable resources -- Nitrogen heterocycles; Chemistry, Organic -- Periodicals; Organic compounds -- Synthesis -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1002/ejoc.201801129
• Languages: English
• ISSNs: 1434-193X

Abstract

Abstract : Levulinic acid, which is one of the most important renewable building blocks derived from lignocellulosic biomass, has been converted in a diversity‐oriented manner into two families of drug‐like bicyclic nitrogen heterocycles. The methodology, endowed with high step economy and operational simplicity, is based on an Ugi multicomponent reaction, which employs amino alcohols as components, followed by a SN 2 cyclization. Noteworthy is the successful synthesis of hexahydro pyrrolodiazepinediones, since the cyclization of the isocyanide‐derived secondary amide onto an alcohol to give a seven‐membered ring was unprecedented. Also enantiopure products have been prepared by using chiral amino alcohols. Abstract : Operationally simple, 2‐step conversion of levulinic acid into bicyclic drug‐like heterocyclic systems.