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Synthesis of 10-Methylacridin-9(10H)-ones through Cu-Catalyzed Intramolecular Oxidative C(sp2)-H Amination of 2-(Methylamino)benzophenones
European Journal of Organic Chemistry ( IF 2.5 ) Pub Date : 2013-02-25 , DOI: 10.1002/ejoc.201201748
Jinbo Huang , Congqing Wan , Ming‐Fang Xu , Qiang Zhu

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.

中文翻译:

10-Methylacridin-9(10H)-ones 通过 Cu 催化的分子内氧化 C(sp2)-H 胺化 2-(甲基氨基)二苯甲酮合成

已开发出一种从 2-(甲基氨基) 二苯甲酮中高效合成多种 10-methylacridin-9(10H)-ones 的方法。该反应通过使用 O2 作为唯一氧化剂通过 Cu 催化的分子内芳族 C-H 胺化进行,以中等至良好的产率提供所需的产物。此外,2-烯丙基氨基-和2-(苄基氨基)二苯甲酮以及未受保护的底物也可以进行C-H胺化反应,从而顺利地生成相应的环化产物。初步的机理研究表明,C-H 活化涉及限速步骤。
更新日期:2013-02-25
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