N-Capping of Primary Amines with 2-Acyl-benzaldehydes To Give Isoindolinones
N-Capping of Primary Amines with 2-Acyl-benzaldehydes To Give Isoindolinones
复制标题
DOI：
10.1021/ol202271k
复制
发表时间：
2011-10-07
期刊：
影响因子：
5.2
通讯作者：
Schmalz, Hans-Guenther
中科院分区：
文献类型：
--
作者：
Augner, Daniel;Gerbino, Dario C.;Schmalz, Hans-Guenther
一个独特的反应模式，首次观察到的海洋天然产物pestalone到pestalachlone A的转换，进行了研究。结果表明，2-甲酰基芳基酮分别与氨和伯胺在温和条件下顺利反应，以高产率得到3-取代异吲哚啉酮。该反应代表了伯胺衍生化（N-封端）的新选择。由于底物容易获得，该方法开启了对药学相关的取代异吲哚啉酮的短且模块化的途径。
A unique reactivity pattern, first observed in the conversion of the marine natural product pestalone into pestalachloride A, was investigated. It was shown that 2-formyl-arylketones smoothly react with ammonia and primary amines, respectively, under mild conditions to afford 3-substituted isoindolinones in high yield. The reaction represents a new option for the derivatization (N-capping) of primary amines. As the substrates are readily accessible the methodology opens a short and modular access to pharmaceutically relevant substituted isoindolinones.