Synthesis of Indole‐Fused 1,4‐Diazepinones via Photoredox‐Catalyzed Cascade Cyclization Reaction
Elisa Brambilla, Silvia Meraviglia, Edoardo Moneta, Donatella Nava, Silvia Rizzato, Giorgio Abbiati, Valentina Pirovano
Abstract
Abstract A photoredox‐promoted approach for the synthesis of [1,4]diazepino[1,7‐ a ]indol‐6(7 H )‐ones starting from N ‐indolyl phenylacrylamides and aroyl chlorides as radical source is reported. This method, that involves a cascade radical addition on C−C double bond followed by intramolecular cyclization at indole C2‐position, affords two diastereomeric indole‐fused 1,4‐diazepinones characterized by a N−C(aryl) axial chirality in yields ranging from 51 to 99%.
Topics & Concepts
ChemistryIndole testDiastereomerIntramolecular forceCascadePhotoredox catalysisCatalysisStereochemistryChirality (physics)PhotocatalysisOrganic chemistryChromatographyQuantum mechanicsNambu–Jona-Lasinio modelChiral symmetry breakingQuarkPhysicsAxial and Atropisomeric Chirality SynthesisCatalytic C–H Functionalization MethodsSynthesis of Indole Derivatives