One-Pot Synthesis of Orange-Red Fluorescent Dimeric 2<i>H</i>-Pyrrolo[2,3-<i>c</i>]isoquinoline-2,5(3<i>H</i>)-diones from Benzamides and Maleimides via Ru(II)-Catalyzed Sequential C–C/C–N/C–C Bond Formation
Yogesh Jaiswal, Saptarshi Mandal, Prolay Das, Amit Kumar
Abstract
We report here a direct and efficient strategy for the synthesis of highly conjugated dimeric pyrrolo-fused isoquinoline derivatives from readily available benzamides and maleimides. This reaction overall proceeds by following a domino approach: C–C bond formation via challenging primary amide-directed Ru(II)-catalyzed ortho alkenylation followed by annulation and C–C bond formation through Ru(II)-catalyzed dehydrogenative dimerization. The resulting products showed substituent-dependent tunable photoluminescence in the orange-red region with reasonably large Stokes shifts and interesting redox properties.
Topics & Concepts
ChemistryIsoquinolineAnnulationDominoFluorescenceSubstituentAmideCombinatorial chemistryRedoxCatalysisConjugated systemStereochemistryMedicinal chemistryOrganic chemistryPolymerPhysicsQuantum mechanicsCatalytic C–H Functionalization MethodsSynthesis and Characterization of PyrrolesCyclopropane Reaction Mechanisms