Synthesis of highly substituted dihydropyrrolophenanthridine derivatives by tandem reaction

The efficient cross-coupling of bromo(iso)quinoline to 1,6-diynes with the Pd-catalyzed system was established. Using unactivated simple diynes with bromo(iso)quinoline in the presence of palladium catalytic system afforded different kinds of rare 7,11-diphenyl-9,10-dihydro-8H-pyrrolo[3,4-j]phenanthridine derivatives through regioselective C–H functionalization in one step. Different diynes (a–p) and different bromo(iso)quinolines were shown to be very active in the reaction. Thus, the generality of this process makes the reaction highly valuable in view of the synthetic and medicinal importance of these pyrrolo[3,4-j]phenanthridine derivatives.