Optimized Conditions for Passerini-Smiles Reactions and Applications to Benzoxazinone Syntheses

Initial conditions disclosed for the Passerini-Smiles reaction are associated with a lack of efficiency that has prevented chemists from using it since its discovery. We wish to report herein our thorough study in the development of new experimental conditions for this coupling between electron-poor...

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Autores principales: Martinand-Lurin, Elodie, Dos Santos, Aurélie, Robineau, Emmanuelle, Retailleau, Pascal, Dauban, Philippe, Grimaud, Laurence, El Kaïm, Laurent
Formato: Online Artículo Texto
Lenguaje:English
Publicado: MDPI 2016
Materias:
Article
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6273966/
https://www.ncbi.nlm.nih.gov/pubmed/27657034
http://dx.doi.org/10.3390/molecules21091257
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author Martinand-Lurin, Elodie
Dos Santos, Aurélie
Robineau, Emmanuelle
Retailleau, Pascal
Dauban, Philippe
Grimaud, Laurence
El Kaïm, Laurent
author_facet Martinand-Lurin, Elodie
Dos Santos, Aurélie
Robineau, Emmanuelle
Retailleau, Pascal
Dauban, Philippe
Grimaud, Laurence
El Kaïm, Laurent
author_sort Martinand-Lurin, Elodie
collection PubMed
description Initial conditions disclosed for the Passerini-Smiles reaction are associated with a lack of efficiency that has prevented chemists from using it since its discovery. We wish to report herein our thorough study in the development of new experimental conditions for this coupling between electron-poor phenols, isocyanides, and carbonyl derivatives. These new conditions have been applied to several synthetic strategies towards benzoxazinones.
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spelling pubmed-62739662018-12-28 Optimized Conditions for Passerini-Smiles Reactions and Applications to Benzoxazinone Syntheses Martinand-Lurin, Elodie Dos Santos, Aurélie Robineau, Emmanuelle Retailleau, Pascal Dauban, Philippe Grimaud, Laurence El Kaïm, Laurent Molecules Article Initial conditions disclosed for the Passerini-Smiles reaction are associated with a lack of efficiency that has prevented chemists from using it since its discovery. We wish to report herein our thorough study in the development of new experimental conditions for this coupling between electron-poor phenols, isocyanides, and carbonyl derivatives. These new conditions have been applied to several synthetic strategies towards benzoxazinones. MDPI 2016-09-21 /pmc/articles/PMC6273966/ /pubmed/27657034 http://dx.doi.org/10.3390/molecules21091257 Text en © 2016 by the authors. Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC-BY) license (http://creativecommons.org/licenses/by/4.0/).
spellingShingle Article
Martinand-Lurin, Elodie
Dos Santos, Aurélie
Robineau, Emmanuelle
Retailleau, Pascal
Dauban, Philippe
Grimaud, Laurence
El Kaïm, Laurent
Optimized Conditions for Passerini-Smiles Reactions and Applications to Benzoxazinone Syntheses
title Optimized Conditions for Passerini-Smiles Reactions and Applications to Benzoxazinone Syntheses
title_full Optimized Conditions for Passerini-Smiles Reactions and Applications to Benzoxazinone Syntheses
title_fullStr Optimized Conditions for Passerini-Smiles Reactions and Applications to Benzoxazinone Syntheses
title_full_unstemmed Optimized Conditions for Passerini-Smiles Reactions and Applications to Benzoxazinone Syntheses
title_short Optimized Conditions for Passerini-Smiles Reactions and Applications to Benzoxazinone Syntheses
title_sort optimized conditions for passerini-smiles reactions and applications to benzoxazinone syntheses
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6273966/
https://www.ncbi.nlm.nih.gov/pubmed/27657034
http://dx.doi.org/10.3390/molecules21091257
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