Synthesis 2012; 44(15): 2374-2384
DOI: 10.1055/s-0032-1316542
paper
© Georg Thieme Verlag Stuttgart · New York

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

Authors

  • 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
Further Information

Publication History

Received: 23 March 2012

Accepted after revision: 15 May 2012

Publication Date:
29 June 2012 (online)


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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.

Supporting Information