Gold(I)‐Catalyzed Selective Cyclization and 1,2‐Shift to Prepare Pseudorutaecarpine Derivatives
Wang Wang, Nan‐Ying Chen, Pei‐Sen Zou, Li Pang, Dong‐Liang Mo, Cheng‐Xue Pan, Gui‐Fa Su
Abstract
Abstract 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. magnified image