Synthesis of Bridged Bicyclic Systems <i>peri</i>‐Annulated to the Indole Ring: Tropane‐Fused Indoles
Sergey M. Antropov, Sofiya A. Tokmacheva, Ирина И. Левина, Оlga А. Ivanova, Igor V. Trushkov
Abstract
Abstract Ytterbium triflate catalysed domino reaction of (3‐formyl‐4‐indolyl)‐derived donor‐acceptor cyclopropane with primary amines provides a simple approach to an unprecedented tetracyclic skeleton in which tropane system is peri ‐annulated with an indole core. This process involves the formation of an imine and its (3+2)‐cross‐cycloaddition with donor‐acceptor cyclopropane moiety, yielding tropane‐fused indole core under mild reaction conditions. These products are of significant interest for pharmacology as potential hybrid molecules with a dual mode of action.
Topics & Concepts
TropaneChemistryBicyclic moleculeIndole testRing (chemistry)StereochemistryOrganic chemistryCyclopropane Reaction MechanismsAsymmetric Synthesis and CatalysisCatalytic C–H Functionalization Methods