Blue LED Mediated Intramolecular C–H Functionalization and Cyclopropanation of Tryptamines: Synthesis of Azepino[4, 5-b]indoles and Natural Product Inspired Polycyclic Indoles
Jyoti Chauhan, Mahesh Kumar Ravva, Ludovic Gremaud, Subhabrata Sen
Abstract
We report a novel blue LED mediated intramolecular C–H functionalization of tryptamine derivatives to generate azepino[4, 5-b]indoles (4) in moderate to good yields. By altering the substitution at the tryptamine nitrogen, intramolecular cyclopropanation is achieved in high yields under the same reactions condition to provide natural product inspired polycyclic indoles (6), which are further transformed to spiropiperidino (5 and 8) indoles in decent yields. The mechanism of formation of the compounds was investigated through DFT studies.
Topics & Concepts
TryptaminesChemistryNatural productIntramolecular forceCyclopropanationCombinatorial chemistryProduct (mathematics)Total synthesisSurface modificationStereochemistryOrganic chemistryTryptamineCatalysisPhysical chemistryMathematicsGeometryBiochemistryCyclopropane Reaction MechanismsCatalytic C–H Functionalization MethodsSynthesis and Catalytic Reactions