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.
authors.affiliation: 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. Elodie.MARTINAND-LURIN@cnrs.fr.|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. Elodie.MARTINAND-LURIN@cnrs.fr.
authors.forename: Elodie
authors.initials: E
authors.lastname: Martinand-Lurin
authors.affiliation: Laboratoire de Synthèse Organique, CNRS, Ecole Polytechnique, ENSTA ParisTech-UMR 7652, Université Paris-Saclay, 91128 Palaiseau, France. aurelie.dossantos@ensta-paristech.fr.
authors.forename: Aurélie
authors.initials: A
authors.lastname: Dos Santos
authors.affiliation: 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. Emmanuelle.robineau@ens.fr.
authors.forename: Emmanuelle
authors.initials: E
authors.lastname: Robineau
authors.affiliation: 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. pascal.retailleau@icsn.cnrs-gif.fr.
authors.forename: Pascal
authors.initials: P
authors.lastname: Retailleau
authors.affiliation: 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@cnrs.fr.
authors.forename: Philippe
authors.initials: P
authors.lastname: Dauban
authors.affiliation: 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. laurence.grimaud@ens.fr.
authors.forename: Laurence
authors.initials: L
authors.lastname: Grimaud
authors.affiliation: Laboratoire de Synthèse Organique, CNRS, Ecole Polytechnique, ENSTA ParisTech-UMR 7652, Université Paris-Saclay, 91128 Palaiseau, France. laurent.elkaim@ensta-paristech.fr.
authors.forename: Laurent
authors.initials: L
authors.lastname: El Kaïm
keywords: Passerini-Smiles; benzoxazinones; heterocycles; isocyanide; multicomponent reaction