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
Affiliations
Elodie Martinand-Lurin
Institut de Chimie des Substances Naturelles, CNRS UPR 2301, Univ. Paris-Sud, Université Paris-Saclay, Avenue de la Terrasse, 91198 Gif-sur-Yvette CEDEX, France
Aurélie Dos Santos
Laboratoire de Synthèse Organique, CNRS, Ecole Polytechnique, ENSTA ParisTech–UMR 7652, Université Paris-Saclay, 91128 Palaiseau, France
Emmanuelle Robineau
1 Ecole Normale Supérieure, PSL Research University, UPMC Univ. Paris 06, CNRS, Département de Chimie, PASTEUR, 24, rue Lhomond, 75005 Paris, France; 2 Sorbonne Universités, UPMC Univ. Paris 06, ENS, CNRS, PASTEUR, 75005 Paris, France
Pascal Retailleau
Institut de Chimie des Substances Naturelles, CNRS UPR 2301, Univ. Paris-Sud, Université Paris-Saclay, Avenue de la Terrasse, 91198 Gif-sur-Yvette CEDEX, France
Philippe Dauban
Institut de Chimie des Substances Naturelles, CNRS UPR 2301, Univ. Paris-Sud, Université Paris-Saclay, Avenue de la Terrasse, 91198 Gif-sur-Yvette CEDEX, France
Laurence Grimaud
1 Ecole Normale Supérieure, PSL Research University, UPMC Univ. Paris 06, CNRS, Département de Chimie, PASTEUR, 24, rue Lhomond, 75005 Paris, France; 2 Sorbonne Universités, UPMC Univ. Paris 06, ENS, CNRS, PASTEUR, 75005 Paris, France
Laurent El Kaïm
Laboratoire de Synthèse Organique, CNRS, Ecole Polytechnique, ENSTA ParisTech–UMR 7652, Université Paris-Saclay, 91128 Palaiseau, France
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.
