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Iron-Catalyzed Cyclization of Nitrones with Geminal-Substituted Vinyl Acetates: A Direct [4 + 2] Assembly Strategy Leading to 2,4-Disubstituted Quinolines

Mingbing Zhong, Song Sun, Jiang Cheng* and Ying Shao*

*School of Petrochemical Engineering, Advanced Catalysis and Green Manufacturing Collaborative Innovation Center, Changzhou University, Changzhou 213164, P. R. China, Email: yingshaocczu.edu.cn, jiangchengcczu.edu.cn

M. Zhong, S. Sun, J. Cheng, Y. Shao, J. Org. Chem., 2016, 81, 10825-10831.

DOI: 10.1021/acs.joc.6b01910


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Abstract

An iron-catalyzed intermolecular [4 + 2] cyclization of arylnitrones with geminal-substituted vinyl acetates enables the synthesis of 2,4-disubstituted quinolines in good yields with good functional group compatibilities. Preliminary mechanistic studies suggest an iron-catalyzed C-H activation process.

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Key Words

quinolines


ID: J42-Y2016