Synthesis of a novel category of pseudo-peptides using an Ugi three-component reaction of levulinic acid as bifunctional substrate, amines, and amino acid-based isocyanides

Maryam Khalesi; Azim Ziyaei Halimehjani; Jürgen Martens

doi:10.3762/bjoc.15.82

Synthesis of a novel category of pseudo-peptides using an Ugi three-component reaction of levulinic acid as bifunctional substrate, amines, and amino acid-based isocyanides

Beilstein J Org Chem. 2019 Apr 4:15:852-857. doi: 10.3762/bjoc.15.82. eCollection 2019.

Authors

Maryam Khalesi¹, Azim Ziyaei Halimehjani¹, Jürgen Martens²

Affiliations

¹ Faculty of Chemistry, Kharazmi University, P.O. Box 15719-14911, 49 Mofateh Street, Tehran, Iran.
² Institut für Chemie (IfC), Carl von Ossietzky Universität Oldenburg, P.O. Box 2503, 26111 Oldenburg, Germany.

Abstract

The synthesis of a novel category of pseudo-peptides via intramolecular Ugi reaction of levulinic acid (4-oxopentanoic acid), aromatic and aliphatic amines, and amino acid-based isocyanides is reported. Levulinic acid was applied as a bifunctional substrate containing both carbonyl and acid moieties suitable for the Ugi reaction. This article provides a facile and convenient one-pot procedure for the synthesis of peptide-like heterocyclic molecules containing 2-pyrrolidone (γ-lactam), amide and ester functional groups with good to excellent yields.

Keywords: Ugi reaction; amino acid-based isocyanides; levulinic acid; multicomponent; pseudo-peptides.