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Molecules 2016, 21(9), 1257;

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

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
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
Laboratoire de Synthèse Organique, CNRS, Ecole Polytechnique, ENSTA ParisTech–UMR 7652, Université Paris-Saclay, 91128 Palaiseau, France
Authors to whom correspondence should be addressed.
Academic Editor: Philippe Belmont
Received: 27 July 2016 / Revised: 13 September 2016 / Accepted: 13 September 2016 / Published: 21 September 2016
(This article belongs to the Collection Heterocyclic Compounds)
Full-Text   |   PDF [6159 KB, uploaded 21 September 2016]   |  


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. View Full-Text
Keywords: isocyanide; Passerini-Smiles; multicomponent reaction; heterocycles; benzoxazinones isocyanide; Passerini-Smiles; multicomponent reaction; heterocycles; benzoxazinones

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This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited (CC BY 4.0).

Supplementary materials

  • Supplementary File 1:

    Supplementary (PDF, 26182 KB)

  • Externally hosted supplementary file 1
    Doi: 10.1039/C3CC49022J
    Description: This supplementary material concerns the Passerini-Smiles optimized for 2-nitrophenol and the anionic rearrangement of the resulting adducts.

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Martinand-Lurin, E.; Dos Santos, A.; Robineau, E.; Retailleau, P.; Dauban, P.; Grimaud, L.; El Kaïm, L. Optimized Conditions for Passerini-Smiles Reactions and Applications to Benzoxazinone Syntheses. Molecules 2016, 21, 1257.

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