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 aminoalcohols as components, followed by a SN2 cyclization. Worth of noting 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 using chiral aminoalcohols.

Diversity-oriented Synthesis of Bicyclic Heterocycles from Levulinic Acid through a Fast and Operationally Simple Multicomponent Approach

Lambruschini, C.;Basso, A.;Moni, L.;Pinna, A.;Riva, R.;Banfi, L.
2018-01-01

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 aminoalcohols as components, followed by a SN2 cyclization. Worth of noting 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 using chiral aminoalcohols.
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Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/11567/927787
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