A Ruthenium-Catalyzed Cyclization to Dihydrobenzo[<i>c</i>]phenanthridinone from 7-Azabenzonorbornadienes with Aryl Amides
N. Aravindan, Varathan Vinayagam, Masilamani Jeganmohan
Abstract
An efficient ruthenium(II)-catalyzed tandem C–C/C–N bond formation with aryl amides and 7-azabenzonorbornadienes has been developed to synthesize cis-fused dihydrobenzo[c]phenanthridinones. The amide group functions as a directing group as well as a leaving group and provides an easy access to the pharmaceutically useful benzo[c]phenanthridine alkaloids such as nitidine and fagaronine analogues. The present methodology is compatible with various functional groups with respect to azabicyclic alkenes and aromatic amides. The reaction mechanism involving directing-group-assisted C–H activation was proposed and supported by the deuterium labeling studies.
Topics & Concepts
ChemistryRutheniumAmidePhenanthridineArylCatalysisTandemFunctional groupStereochemistryCombinatorial chemistryDeuteriumMedicinal chemistryGroup (periodic table)Organic chemistryPhysicsPolymerMaterials scienceQuantum mechanicsAlkylComposite materialCatalytic C–H Functionalization MethodsAsymmetric Hydrogenation and CatalysisAdvanced Synthetic Organic Chemistry