化学
重氮
分子内力
卡宾
烷氧基
部分
催化作用
金属化
组合化学
迁移插入
立体化学
插入反应
废止
药物化学
有机化学
烷基
作者
Manqing Wang,Qianting Zhou,Xinying Zhang,Xuesen Fan
标识
DOI:10.1002/adsc.202300085
摘要
Abstract Presented herein is a condition‐controlled divergent synthesis of imidazoindolone spiro‐isoquinolinones (IISIQs) via the cascade reactions of N ‐alkoxycarboxamide indoles with diazo homophthalimides. When the reaction is carried out under air and in the absence of an acid additive, IISIQ tethered with a N ‐alkoxy moiety (IISIQ‐OR) is formed through Rh(III)‐catalyzed C−H/N−H metalation, carbene formation/ migratory insertion followed by reductive elimination, in which air acts as an oxidant to regenerate the Rh(III) catalyst. When the reaction is run under argon and in the presence of MesCO 2 H, on the other hand, IISIQ−H is formed through rhodacycle intermediate formation, carbene insertion followed by acid‐assisted intramolecular substitution/annulation and N−O bond cleavge. In general, this method provides a divergent approach toward spiroheterocyclic scaffolds and features accessible substrates, functional group compatibility and air as an external oxidant. Moreover, the value of this developed protocol is further showcased by gram‐scale synthesis and structural transformation of products. magnified image
科研通智能强力驱动
Strongly Powered by AbleSci AI