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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

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...

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Autores principales: Khalesi, Maryam, Ziyaei Halimehjani, Azim, Martens, Jürgen
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Beilstein-Institut 2019
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6466677/
https://www.ncbi.nlm.nih.gov/pubmed/31019577
http://dx.doi.org/10.3762/bjoc.15.82
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author Khalesi, Maryam
Ziyaei Halimehjani, Azim
Martens, Jürgen
author_facet Khalesi, Maryam
Ziyaei Halimehjani, Azim
Martens, Jürgen
author_sort Khalesi, Maryam
collection PubMed
description 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.
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spelling pubmed-64666772019-04-24 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 Khalesi, Maryam Ziyaei Halimehjani, Azim Martens, Jürgen Beilstein J Org Chem Full Research Paper 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. Beilstein-Institut 2019-04-04 /pmc/articles/PMC6466677/ /pubmed/31019577 http://dx.doi.org/10.3762/bjoc.15.82 Text en Copyright © 2019, Khalesi et al. https://creativecommons.org/licenses/by/4.0https://www.beilstein-journals.org/bjoc/termsThis is an Open Access article under the terms of the Creative Commons Attribution License (https://creativecommons.org/licenses/by/4.0). Please note that the reuse, redistribution and reproduction in particular requires that the authors and source are credited. The license is subject to the Beilstein Journal of Organic Chemistry terms and conditions: (https://www.beilstein-journals.org/bjoc/terms)
spellingShingle Full Research Paper
Khalesi, Maryam
Ziyaei Halimehjani, Azim
Martens, Jürgen
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
title 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
title_full 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
title_fullStr 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
title_full_unstemmed 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
title_short 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
title_sort 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
topic Full Research Paper
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6466677/
https://www.ncbi.nlm.nih.gov/pubmed/31019577
http://dx.doi.org/10.3762/bjoc.15.82
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