Formation of amides: one-pot condensation of carboxylic acids and amines mediated by TiCl(4)

A general procedure for the synthesis of amides via the direct condensation of carboxylic acids and amines in the presence of TiCl(4) is reported. The amidation reaction was performed in pyridine at 85 °C with a wide range of substrates providing the corresponding amide products in moderate to excel...

Descripción completa

Detalles Bibliográficos
Autores principales: Leggio, Antonella, Bagalà, Jessica, Belsito, Emilia Lucia, Comandè, Alessandra, Greco, Marianna, Liguori, Angelo
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Springer International Publishing 2017
Materias:
Research Article
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5602818/
https://www.ncbi.nlm.nih.gov/pubmed/29086872
http://dx.doi.org/10.1186/s13065-017-0318-9
_version_ 1783264627006636032
author Leggio, Antonella
Bagalà, Jessica
Belsito, Emilia Lucia
Comandè, Alessandra
Greco, Marianna
Liguori, Angelo
author_facet Leggio, Antonella
Bagalà, Jessica
Belsito, Emilia Lucia
Comandè, Alessandra
Greco, Marianna
Liguori, Angelo
author_sort Leggio, Antonella
collection PubMed
description A general procedure for the synthesis of amides via the direct condensation of carboxylic acids and amines in the presence of TiCl(4) is reported. The amidation reaction was performed in pyridine at 85 °C with a wide range of substrates providing the corresponding amide products in moderate to excellent yields and high purity. The reaction proceeds with low yields when both the carboxylic acid and the amine are sterically hindered. The process takes place with nearly complete preservation of the stereochemical integrity of chiral substrates. ELECTRONIC SUPPLEMENTARY MATERIAL: The online version of this article (doi:10.1186/s13065-017-0318-9) contains supplementary material, which is available to authorized users.
format Online
Article
Text
id pubmed-5602818
institution National Center for Biotechnology Information
language English
publishDate 2017
publisher Springer International Publishing
record_format MEDLINE/PubMed
spelling pubmed-56028182017-09-27 Formation of amides: one-pot condensation of carboxylic acids and amines mediated by TiCl(4) Leggio, Antonella Bagalà, Jessica Belsito, Emilia Lucia Comandè, Alessandra Greco, Marianna Liguori, Angelo Chem Cent J Research Article A general procedure for the synthesis of amides via the direct condensation of carboxylic acids and amines in the presence of TiCl(4) is reported. The amidation reaction was performed in pyridine at 85 °C with a wide range of substrates providing the corresponding amide products in moderate to excellent yields and high purity. The reaction proceeds with low yields when both the carboxylic acid and the amine are sterically hindered. The process takes place with nearly complete preservation of the stereochemical integrity of chiral substrates. ELECTRONIC SUPPLEMENTARY MATERIAL: The online version of this article (doi:10.1186/s13065-017-0318-9) contains supplementary material, which is available to authorized users. Springer International Publishing 2017-09-15 /pmc/articles/PMC5602818/ /pubmed/29086872 http://dx.doi.org/10.1186/s13065-017-0318-9 Text en © The Author(s) 2017 Open AccessThis article is distributed under the terms of the Creative Commons Attribution 4.0 International License (http://creativecommons.org/licenses/by/4.0/), which permits unrestricted use, distribution, and reproduction in any medium, provided you give appropriate credit to the original author(s) and the source, provide a link to the Creative Commons license, and indicate if changes were made. The Creative Commons Public Domain Dedication waiver (http://creativecommons.org/publicdomain/zero/1.0/) applies to the data made available in this article, unless otherwise stated.
spellingShingle Research Article
Leggio, Antonella
Bagalà, Jessica
Belsito, Emilia Lucia
Comandè, Alessandra
Greco, Marianna
Liguori, Angelo
Formation of amides: one-pot condensation of carboxylic acids and amines mediated by TiCl(4)
title Formation of amides: one-pot condensation of carboxylic acids and amines mediated by TiCl(4)
title_full Formation of amides: one-pot condensation of carboxylic acids and amines mediated by TiCl(4)
title_fullStr Formation of amides: one-pot condensation of carboxylic acids and amines mediated by TiCl(4)
title_full_unstemmed Formation of amides: one-pot condensation of carboxylic acids and amines mediated by TiCl(4)
title_short Formation of amides: one-pot condensation of carboxylic acids and amines mediated by TiCl(4)
title_sort formation of amides: one-pot condensation of carboxylic acids and amines mediated by ticl(4)
topic Research Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5602818/
https://www.ncbi.nlm.nih.gov/pubmed/29086872
http://dx.doi.org/10.1186/s13065-017-0318-9
work_keys_str_mv AT leggioantonella formationofamidesonepotcondensationofcarboxylicacidsandaminesmediatedbyticl4
AT bagalajessica formationofamidesonepotcondensationofcarboxylicacidsandaminesmediatedbyticl4
AT belsitoemilialucia formationofamidesonepotcondensationofcarboxylicacidsandaminesmediatedbyticl4
AT comandealessandra formationofamidesonepotcondensationofcarboxylicacidsandaminesmediatedbyticl4
AT grecomarianna formationofamidesonepotcondensationofcarboxylicacidsandaminesmediatedbyticl4
AT liguoriangelo formationofamidesonepotcondensationofcarboxylicacidsandaminesmediatedbyticl4

Ejemplares similares