Ikawa Takashi, Urata Hirohito, Fukumoto Yutaka, Sumii Yuta, Nishiyama Tsuyoshi, Akai Shuji
Graduate School of Pharmaceutical Sciences, Osaka University, 1-6 Yamadaoka, Suita, Osaka 565-0871 (Japan), Fax: (+81) 6-6879-8212, (+81) 6-6879-8210.
Chemistry. 2014 Dec 1;20(49):16228-32. doi: 10.1002/chem.201404633. Epub 2014 Oct 13.
A four-step regioselective synthesis of multisubstituted isoquinoline derivatives from 3-bromopyridines was developed by the Diels-Alder (DA) reactions of 2-silyl-3,4-pyridynes with furans, followed by functional-group transformations. In particular, the silyl group at the C2-position of the 3,4-pyridynes played two important roles: firstly, it functioned as the directing group for the DA reaction, and secondly, it served to introduce diverse substituents at the C1-position of the isoquinolines by electrophilic ipso-substitution.
通过2-硅基-3,4-吡啶炔与呋喃的狄尔斯-阿尔德（DA）反应，随后进行官能团转化，开发了一种从3-溴吡啶出发的多取代异喹啉衍生物的四步区域选择性合成方法。特别地，3,4-吡啶炔C2位的硅基发挥了两个重要作用：首先，它作为DA反应的导向基团；其次，它通过亲电原位取代在异喹啉的C1位引入各种取代基。
