Journal
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
Volume 2013, Issue 10, Pages 1876-1880Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/ejoc.201201748
Keywords
Nitrogen heterocycles; Fused-ring systems; Amination; Copper; C-H activation
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Funding
- National Natural Science Foundation of China (NSFC) [21072190, 21202167]
- Science Foundation of Guangdong Province, China [S2011020000806]
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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 O-2 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.
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