Instituto de Química, Universidad Nacional Autónoma de México, Circuito Exterior, Ciudad Universitaria, Coyoacán, México D.F. 04510, Mexico.
Org Biomol Chem. 2022 Sep 21;20(36):7325-7331. doi: 10.1039/d2ob01304e.
Divergent C(sp)-H bond functionalizations of isoindolinone derivatives were developed to synthesize nuevamine, a cyano-chilenine derivative, and two related analogs. A copper-catalyzed C-H cross-dehydrogenative coupling ( cation formation) allowed the formation of a new C-C bond leading to the direct assembly of the isoindolo[1,2-]isoquinolinone tetracyclic system of the nuevamine. The syntheses of the cyano-chilenine derivatives were carried out by installing two nitrile groups under basic conditions ( anion formation). Then, the isoindolobenzazepinic system of the chilenine skeleton was constructed by a Houben-Hoesch cyclization process. The present methodology has the advantage of not requiring the use of pre-functionalized substrates.
发展了异吲哚酮衍生物的发散 C(sp^2)-H 键功能化方法，以合成新型南美蟾毒色胺衍生物，以及两种相关类似物。铜催化的 C-H 交叉脱氢偶联（阳离子形成）允许形成新的 C-C 键，从而直接组装新型南美蟾毒色胺的异吲哚并[1,2-]异喹啉酮四环体系。通过在碱性条件下（阴离子形成）引入两个腈基基团，完成了新型南美蟾毒色胺衍生物的合成。然后，通过 Houben-Hoesch 环化过程构建了南美蟾毒色胺骨架的异吲哚并苯并氮杂卓系统。本方法的优点是不需要使用预官能化的底物。
