Gold(I)-Catalyzed Selective Cyclization and 1,2-Shift to Prepare Pseudorutaecarpine Derivatives

A variety of pseudorutaecarpine derivatives were prepared in good to excellent yields through a gold(I)-catalyzed selective cyclization and 1,2-shift of N-alkynyl quinazolinone-tethered indoles. Mechanistic study revealed that spiroindolenines generated in situ by cyclization at the the indole C3 position underwent an alkenyl 1,2-shift to generate pseudorutaecarpine. The reaction proceeds under mild reaction conditions, has a broad substrate scope, good functional group tolerance, and gram-scalable application. Furthermore, biological evaluation showed that most of the pseudorutaecarpine scaffolds prepared exhibit anti-inflammatory activity.

Automated summary

A variety of pseudorutaecarpine derivatives were successfully prepared in good to excellent yields through a gold(I)-catalyzed selective cyclization and N-alkynyl quinazolinone-tethered indoles. These derivatives exhibit anti-inflammatory activity, and the reaction conditions are mild with a broad substrate scope.