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Short Communication
Synthesis of 10-Methylacridin-9(10H)-ones through Cu-Catalyzed Intramolecular Oxidative C(sp2)–H Amination of 2-(Methylamino)benzophenones
Article first published online: 25 FEB 2013
DOI: 10.1002/ejoc.201201748
Copyright © 2013 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim
Additional Information
How to Cite
Huang, J., Wan, C., Xu, M.-F. and Zhu, Q. (2013), Synthesis of 10-Methylacridin-9(10H)-ones through Cu-Catalyzed Intramolecular Oxidative C(sp2)–H Amination of 2-(Methylamino)benzophenones. Eur. J. Org. Chem., 2013: 1876–1880. doi: 10.1002/ejoc.201201748
Publication History
- Issue published online: 19 MAR 2013
- Article first published online: 25 FEB 2013
- Manuscript Received: 27 DEC 2012
Keywords:
- Nitrogen heterocycles;
- Fused-ring systems;
- Amination;
- Copper;
- C–H activation
Abstract
An efficient synthesis of a diverse set of 10-methylacridin-9(10H)-ones from 2-(methylamino)benzophenones has been developed. The reaction proceeds though Cu-catalyzed intramolecular aromatic C–H amination by using O2 as the sole oxidant to provide the desired products in moderate to good yields. In addition, 2-allylamino- and 2-(benzylamino)benzophenones as well as unprotected substrates can also undergo the C–H amination reaction to deliver the corresponding cyclization products smoothly. Preliminary mechanistic studies suggest that C–H activation is involved in a rate-limiting step.