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Bicyclic Heterocycles from Levulinic Acid through a Fast and Operationally Simple Diversity‐Oriented Multicomponent Approach
Author(s) -
Lambruschini Chiara,
Basso Andrea,
Moni Lisa,
Pinna Alessandro,
Riva Renata,
Banfi Luca
Publication year - 2018
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201801129
Subject(s) - chemistry , levulinic acid , bicyclic molecule , enantiopure drug , organic chemistry , amide , isocyanide , combinatorial chemistry , enantioselective synthesis , catalysis
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 S N 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.