A Synthesis of Spirooxindole-Isoindolinones Through Ugi Reaction Followed by Copper-Catalyzed Tandem C-N/C-C Coupling Process

A synthesis of spiroindolinone-isoindolinone skeletons is presented. The protocol is through a Ugi four-component reaction followed by highly efficient and mild copper-catalyzed intramolecular tandem C-N/C-C coupling process. Control experiments demonstrated that the formation of C-C bond is a copper catalyzed coupling process rather than base promoted nucleophilic aromatic substitution pathway which proposed in Prof. Van der Eycken's palladium catalyst system previously.

Automated summary

The synthesis of spiroindolinone-isoindolinone skeletons was achieved through a Ugi four-component reaction followed by a highly efficient and mild copper-catalyzed intramolecular tandem C-N/C-C coupling process. Control experiments confirmed that the formation of the C-C bond occurred via a copper-catalyzed coupling process, in contrast to the previously proposed base-promoted nucleophilic aromatic substitution pathway in Prof. Van der Eycken's palladium catalyst system.