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用于Passerini-Smiles反应的优化条件及其在苯并恶嗪酮合成中的应用

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

作者信息

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

机构信息

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.

出版信息

Molecules. 2016 Sep 21;21(9):1257. doi: 10.3390/molecules21091257.

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.

摘要

帕塞里尼-施密尔斯反应最初公开的条件存在效率低下的问题,自该反应被发现以来,这一直阻碍着化学家对其的使用。在此,我们希望报告我们对贫电子酚、异腈和羰基衍生物之间这种偶联反应新实验条件开发的深入研究。这些新条件已应用于多种合成苯并恶嗪酮的策略中。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/3a0e/6273966/735a6401e053/molecules-21-01257-sch001.jpg

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