Affiliation:
1. Pingyuan Laboratory Collaborative Innovation Center of Henan Province for Green Manufacturing of Fine Chemicals Key Laboratory of Green Chemical Media and Reactions Ministry of Education School of Chemistry and Chemical Engineering Henan Normal University Xinxiang Henan 453007, People's Republic of China
Abstract
AbstractPresented herein is a condition‐controlled divergent synthesis of imidazoindolone spiro‐isoquinolinones (IISIQs) via the cascade reactions ofN‐alkoxycarboxamide indoles with diazo homophthalimides. When the reaction is carried out under air and in the absence of an acid additive, IISIQ tethered with aN‐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 MesCO2H, 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
Funder
National Natural Science Foundation of China
Natural Science Foundation of Henan Province
Henan Key Laboratory of Organic Functional Molecules and Drug Innovation
Higher Education Discipline Innovation Project
Cited by
1 articles.
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