Synlett 2013; 24(8): 1016-1020
DOI: 10.1055/s-0032-1316898
letter
© Georg Thieme Verlag Stuttgart · New York

Synthesis of Phenanthridin-6(5H)-ones via Copper-Catalyzed Cyclization of 2-Phenylbenzamides

Qingwen Gui
a   State Key Laboratory of Chemo/Biosensing and Chemometrics, College of Chemistry and Chemical Engineering, Hunan University, Changsha 410082, P. R. of China   Email: ztanze@gmail.com
,
Zhiyong Yang
a   State Key Laboratory of Chemo/Biosensing and Chemometrics, College of Chemistry and Chemical Engineering, Hunan University, Changsha 410082, P. R. of China   Email: ztanze@gmail.com
,
Xiang Chen
a   State Key Laboratory of Chemo/Biosensing and Chemometrics, College of Chemistry and Chemical Engineering, Hunan University, Changsha 410082, P. R. of China   Email: ztanze@gmail.com
,
Jidan Liu
a   State Key Laboratory of Chemo/Biosensing and Chemometrics, College of Chemistry and Chemical Engineering, Hunan University, Changsha 410082, P. R. of China   Email: ztanze@gmail.com
,
Ze Tan*
a   State Key Laboratory of Chemo/Biosensing and Chemometrics, College of Chemistry and Chemical Engineering, Hunan University, Changsha 410082, P. R. of China   Email: ztanze@gmail.com
,
Ruqing Guo
a   State Key Laboratory of Chemo/Biosensing and Chemometrics, College of Chemistry and Chemical Engineering, Hunan University, Changsha 410082, P. R. of China   Email: ztanze@gmail.com
,
Wei Yu*
b   Pharmaceutical Department, Kunming General Hospital of PLA, Kunming Yunnan 60032, P. R. of China   Email: kmweiyu@163.com
› Author Affiliations
Further Information

Publication History

Received: 25 January 2013

Accepted after revision: 12 March 2013

Publication Date:
28 March 2013 (online)


Abstract

Synthesis of phenanthridin-6(5H)-ones was achieved via copper-catalyzed cyclization of 2-phenylbenzamides using air as the oxidant and KOt-Bu as the base. It was discovered that, besides Ph3P, other ligands such as 1,10-phenanthroline, TMEDA as well as l-proline could also be used as the ligand to effect the transformation.

Supporting Information