Divergent C–H Annulation for Multifused N‐Heterocycles: Regio‐ and Stereospecific Cyclizations of N‐Alkynylindoles

Abstract

AbstractN‐Alkynylindoles were divergently cyclized for the synthesis of multifused N‐heterocycles. An ortho‐aryl palladium species was added to the α position of an ynamine to generate (Z)‐6‐alkylidene/benzylidene‐6H‐isoindolo[2,1‐a]indoles, while Pt‐catalyzed β‐addition through π‐activation gave 5‐alkyl/arylindolo[2,1‐a]isoquinolines. Double cyclizations using PdCl2 and oxidant afforded bright yellow benzo[7,8]indolizino[2,3,4,5‐ija]quinolines, the synthesis of which was also demonstrated in a different synthetic route.