The 1st Part: copper-catalyzed cascade reaction of C–O and C–N bond coupling. This method efficiently provides poly-substituted (NH)- phenanthridinones in moderate to good yields with tolerance of a wide variety of substrates. The 2st Part: copper-catalyzed annulation reaction involving addition of the Grignard reagent to nitrile and C–N bond coupling. This method efficiently provides poly-substituted phenanthridines in moderate to good yields with tolerance of a very wide variety of substrates.