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Synthesis of 10‐Methylacridin‐9(10 H )‐ones through Cu‐Catalyzed Intramolecular Oxidative C(sp 2 )–H Amination of 2‐(Methylamino)benzophenones
Author(s) -
Huang Jinbo,
Wan Congqing,
Xu MingFang,
Zhu Qiang
Publication year - 2013
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201201748
Subject(s) - chemistry , amination , intramolecular force , catalysis , limiting , medicinal chemistry , oxidative phosphorylation , reductive amination , stereochemistry , combinatorial chemistry , organic chemistry , mechanical engineering , biochemistry , engineering
An efficient synthesis of a diverse set of 10‐methylacridin‐9(10 H )‐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.