Zhou Wen, Zhang Yan-Xue, Nie Xiao-Di, Si Chang-Mei, Sun Xun, Wei Bang-Guo
Department of Natural Products Chemistry, School of Pharmacy , Fudan University , 826 Zhangheng Road , Shanghai , 201203 , The People's Republic of China.
J Org Chem. 2018 Sep 7;83(17):9879-9889. doi: 10.1021/acs.joc.8b01282. Epub 2018 Jul 16.
An approach to access 1-substituted isoquinolones has been developed through the addition-cyclization of imines with Grignard reagents in the presence of 2,2'-dipyridyl. A number of substituted aromatic magnesium reagents were amenable to this process, and the desired products were obtained with excellent yields and outstanding diastereoselectivities ( dr > 99:1). The utility of this convenient approach is demonstrated by the formal synthesis of ( S)-cryptostyline II. Moreover, N-methylmorpholine (NMM) was found to be an effective additive for the formation of 3-substituted isoindolin-1-ones using one-pot addition-cyclization-deprotection of imine with Grignard reagents.
通过在2,2'-联吡啶存在下亚胺与格氏试剂的加成环化反应，开发了一种制备1-取代异喹啉酮的方法。许多取代的芳基镁试剂适用于该反应过程，并且以优异的产率和出色的非对映选择性（dr>99:1）得到了所需产物。(S)-隐喹啉碱II的形式合成证明了这种简便方法的实用性。此外，发现N-甲基吗啉（NMM）是使用亚胺与格氏试剂一锅法进行加成环化-脱保护反应形成3-取代异吲哚啉-1-酮的有效添加剂。
