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.
File in questo prodotto:
File Dimensione Formato  
ejoc18_5445.pdf

accesso chiuso

Tipologia: Documento in versione editoriale
Dimensione 1.32 MB
Formato Adobe PDF
1.32 MB Adobe PDF   Visualizza/Apri   Richiedi una copia

I documenti in IRIS sono protetti da copyright e tutti i diritti sono riservati, salvo diversa indicazione.

Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/11567/927787
Citazioni
  • ???jsp.display-item.citation.pmc??? ND
  • Scopus 18
  • ???jsp.display-item.citation.isi??? 18
social impact