Manganese(III) Acetate Mediated Oxidative Radical Cyclizations of N-(2-Alkenylaryl)-Substituted Enamines

Pei-Ju Tsai; Chih-Bo Kao; Wan-Ru Chiow; Che-Ping Chuang

doi:10.1055/s-0033-1338561

Synthesis, Table of Contents

Synthesis 2014; 46(02): 175-182
DOI: 10.1055/s-0033-1338561

paper

Manganese(III) Acetate Mediated Oxidative Radical Cyclizations of N-(2-Alkenylaryl)-Substituted Enamines

Pei-Ju Tsai

Department of Chemistry, National Cheng Kung University, Tainan, 70101, Taiwan Fax: +886(6)2740552 Email: cpchuang@mail.ncku.edu.tw

,

Chih-Bo Kao

Department of Chemistry, National Cheng Kung University, Tainan, 70101, Taiwan Fax: +886(6)2740552 Email: cpchuang@mail.ncku.edu.tw

,

Wan-Ru Chiow

Department of Chemistry, National Cheng Kung University, Tainan, 70101, Taiwan Fax: +886(6)2740552 Email: cpchuang@mail.ncku.edu.tw

,

Che-Ping Chuang*

Department of Chemistry, National Cheng Kung University, Tainan, 70101, Taiwan Fax: +886(6)2740552 Email: cpchuang@mail.ncku.edu.tw

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Abstract

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Abstract

A method has been developed for the synthesis of highly functionalized quinolines from readily available N-(2-alkenylaryl)-substituted enamines via a 6-exo-trig radical cyclization of an imine radical. Several useful functional groups including morpholinocarbonyl, benzoyl, and cyano, are compatible with the reaction conditions. Under the Mn(II)/Co(II)/O₂ redox system, these N-(2-alkenylaryl)enamines were also converted into the corresponding quinolines effectively. This strategy was further applied to related 1,4-naphthoquinone derivatives, and benzo[b]acridine-6,11-diones were formed in good yields.

Key words

manganese(III) acetate - oxidative - free radical - enamines - quinolines

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References

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