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

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
› Author Affiliations
Further Information

Publication History

Received: 23 March 2012

Accepted after revision: 15 May 2012

Publication Date:
29 June 2012 (online)


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