N-Halosuccinimide enables cascade oxidative trifluorination and halogenative cyclization of tryptamine-derived isocyanides.

ABSTRACT: Both the pyrroloindoline core and N-CF₃ moiety hold significant importance in medicinal chemistry. However, to date, no instances of constructing N-CF₃-containing pyrroloindolines have been reported. Herein, we present a robust and operationally simple approach to assembling such intriguing skeletons from tryptamine-derived isocyanides through a cascade sequence, which includes an oxidative trifluorination and a subsequent halogenative cyclization. Key to the success lies in the development of a facile conversion of isocyanides to N-CF₃ moiety with commercially available reagents N-halosuccinimide and Et₃N·HF. The protocol features mild reaction conditions, broad functional group tolerance, good to excellent yields, and high diastereoselectivitie

SUBMITTER: Wu JY 

PROVIDER: S-EPMC11484912 | biostudies-literature | 2024 Oct

REPOSITORIES: biostudies-literature