Mn(I)-Catalyzed Preferential Electrophilic C3-Maleimidation in Quinoxaline Leading to Spirocyclization and Dehydrogenation of Succinimides
Subhendu Ghosh, Tamanna Khandelia, Pritishree Panigrahi, Raju Mandal, Bhisma K. Patel
Abstract
A Mn(I)-catalyzed site-selective nondirected C3-maleimidation of quinoxaline is established. Herein, the electrophilic C3-metalation precedes over the o -directed strategy to access diversely substituted quinoxaline-appended succinimides. The products undergo PIFA-promoted C(sp 2 )–C(sp 3 ) spirocyclization via π-electrons drifting from aryls and Selectfluor-mediated dehydrogenation of succinimide at room temperature.
Topics & Concepts
SuccinimidesQuinoxalineChemistrySuccinimideDehydrogenationElectrophileSelectfluorCatalysisCombinatorial chemistryMedicinal chemistryOrganic chemistryCatalytic C–H Functionalization MethodsSynthesis and Biological EvaluationCyclopropane Reaction Mechanisms