Optimized conditions for Passerini-Smiles reactions and applications to benzoxazinone syntheses

Elodie Martinand-Lurin; Aurélie Dos Santos; Emmanuelle Robineau; Pascal Retailleau; Philippe Dauban; Laurence Grimaud; Laurent El Kaïm

doi:10.3390/molecules21091257

Optimized conditions for Passerini-Smiles reactions and applications to benzoxazinone syntheses

Elodie Martinand-Lurin
, Aurélie Dos Santos
, Emmanuelle Robineau
, Pascal Retailleau
, Philippe Dauban
, Laurence Grimaud
, Laurent El Kaïm

Institut de Chimie des Substances Naturelles
Ecole Normale Supérieure
PSL Research University
UPMC Univ. Paris 06
PSL research University & IPSL
Université Paris-Saclay

Research output: Contribution to journal › Article › peer-review

6 Citations (Scopus)

Abstract

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.

Original language	English
Article number	1257
Journal	Molecules
Volume	21
Issue number	9
DOIs	https://doi.org/10.3390/molecules21091257
Publication status	Published - 1 Sept 2016
Externally published	Yes

Keywords

Benzoxazinones
Heterocycles
Isocyanide
Multicomponent reaction
Passerini-Smiles

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10.3390/molecules21091257

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title = "Optimized conditions for Passerini-Smiles reactions and applications to benzoxazinone syntheses",

abstract = "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.",

keywords = "Benzoxazinones, Heterocycles, Isocyanide, Multicomponent reaction, Passerini-Smiles",

author = "Elodie Martinand-Lurin and \{Dos Santos\}, Aur{\'e}lie and Emmanuelle Robineau and Pascal Retailleau and Philippe Dauban and Laurence Grimaud and \{El Ka{\"i}m\}, Laurent",

note = "Publisher Copyright: {\textcopyright} 2016 by the authors; licensee MDPI.",

year = "2016",

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doi = "10.3390/molecules21091257",

language = "English",

volume = "21",

journal = "Molecules",

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T1 - Optimized conditions for Passerini-Smiles reactions and applications to benzoxazinone syntheses

AU - Martinand-Lurin, Elodie

AU - Dos Santos, Aurélie

AU - Robineau, Emmanuelle

AU - Retailleau, Pascal

AU - Dauban, Philippe

AU - Grimaud, Laurence

AU - El Kaïm, Laurent

PY - 2016/9/1

Y1 - 2016/9/1

N2 - 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.

AB - 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.

KW - Benzoxazinones

KW - Heterocycles

KW - Isocyanide

KW - Multicomponent reaction

KW - Passerini-Smiles

U2 - 10.3390/molecules21091257

DO - 10.3390/molecules21091257

M3 - Article

AN - SCOPUS:84988973862

SN - 1420-3049

VL - 21

JO - Molecules

JF - Molecules

IS - 9

M1 - 1257

ER -

Optimized conditions for Passerini-Smiles reactions and applications to benzoxazinone syntheses

Abstract

Keywords

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