Copper(II)-Mediated Cascade Oxidative C–C Coupling and Aromatization: Synthesis of 3-Hydroxyphenanthridinone Derivatives

Qingzhen Yu; Nan Zhang; Yang Tang; Hang Lu; Jianhui Huang; Songqing Wang; Yunfei Du; Kang Zhao

doi:10.1055/s-0032-1316542

Synthesis, Table of Contents

Synthesis 2012; 44(15): 2374-2384
DOI: 10.1055/s-0032-1316542

paper

Copper(II)-Mediated Cascade Oxidative C–C Coupling and Aromatization: Synthesis of 3-Hydroxyphenanthridinone Derivatives

Qingzhen Yu

Tianjin Key Laboratory for Modern Drug Delivery & High-Efficiency, School of Pharmaceutical Science and Technology, Tianjin University, Tianjin 300072, P. R. of China, Fax: +86(22)27404031 Email: duyunfeier@tju.edu.cn Email: kangzhao@tju.edu.cn

,

Nan Zhang

Tianjin Key Laboratory for Modern Drug Delivery & High-Efficiency, School of Pharmaceutical Science and Technology, Tianjin University, Tianjin 300072, P. R. of China, Fax: +86(22)27404031 Email: duyunfeier@tju.edu.cn Email: kangzhao@tju.edu.cn

,

Yang Tang

Tianjin Key Laboratory for Modern Drug Delivery & High-Efficiency, School of Pharmaceutical Science and Technology, Tianjin University, Tianjin 300072, P. R. of China, Fax: +86(22)27404031 Email: duyunfeier@tju.edu.cn Email: kangzhao@tju.edu.cn

,

Hang Lu

Tianjin Key Laboratory for Modern Drug Delivery & High-Efficiency, School of Pharmaceutical Science and Technology, Tianjin University, Tianjin 300072, P. R. of China, Fax: +86(22)27404031 Email: duyunfeier@tju.edu.cn Email: kangzhao@tju.edu.cn

,

Jianhui Huang

Tianjin Key Laboratory for Modern Drug Delivery & High-Efficiency, School of Pharmaceutical Science and Technology, Tianjin University, Tianjin 300072, P. R. of China, Fax: +86(22)27404031 Email: duyunfeier@tju.edu.cn Email: kangzhao@tju.edu.cn

,

Songqing Wang

Tianjin Key Laboratory for Modern Drug Delivery & High-Efficiency, School of Pharmaceutical Science and Technology, Tianjin University, Tianjin 300072, P. R. of China, Fax: +86(22)27404031 Email: duyunfeier@tju.edu.cn Email: kangzhao@tju.edu.cn

,

Yunfei Du*

Tianjin Key Laboratory for Modern Drug Delivery & High-Efficiency, School of Pharmaceutical Science and Technology, Tianjin University, Tianjin 300072, P. R. of China, Fax: +86(22)27404031 Email: duyunfeier@tju.edu.cn Email: kangzhao@tju.edu.cn

,

Kang Zhao*

Tianjin Key Laboratory for Modern Drug Delivery & High-Efficiency, School of Pharmaceutical Science and Technology, Tianjin University, Tianjin 300072, P. R. of China, Fax: +86(22)27404031 Email: duyunfeier@tju.edu.cn Email: kangzhao@tju.edu.cn

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Abstract

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Abstract

A novel copper(II) acetate mediated synthesis of 3-hydroxyphenanthridin-6(5H)-ones from N-(3-oxocyclohex-1-enyl)benzamides was developed. The process is postulated to involve an intramolecular oxidative C(sp²)–C(sp³) bond formation followed by dehydrogenative aromatization.

Key words

copper(II) acetate - phenanthridinone - C–H functionalization - C–C oxidative coupling - dehydrogenative aromatization

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References

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11 We thank one reviewer for suggesting such non-metallic hypervalent iodine oxidants for this cross-coupling and dehydrogenative reaction.
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