Access to Polycyclic Indole-3,4-Fused Nine-Membered Ring via Cascade 1,6-Hydride Transfer/Cyclization
Shuo Yang, Xiao‐De An, Bin Qiu, Rui-Bin Liu, Jian Xiao
Abstract
A cascade aldimine condensation/1,6-hydride transfer/Mannich-type cyclization of indole-derived phenylenediamine with aldehydes was developed for one-step construction of a polycyclic indole-3,4-fused skeleton. Aldehyde serves as a key to start the whole process, including 1,6-hydride transfer enabled δ-C(sp3)–H activation of the secondary amine. The challenges of construction of medium-sized rings are addressed via hydride transfer chemistry.
Topics & Concepts
ChemistryHydrideIndole testAldimineCascadeRing (chemistry)Combinatorial chemistryAmine gas treatingCondensationAldehydeStereochemistryOrganic chemistryMedicinal chemistryCatalysisMetalPhysicsChromatographyThermodynamicsCatalytic C–H Functionalization MethodsSynthesis and Catalytic ReactionsAsymmetric Synthesis and Catalysis