Direct diversification of unmasked quinazolin-4(3H)-ones through orthogonal reactivity modulationElectronic supplementary information (ESI) available: Additional tables, experimental procedures, and NMR spectra. See DOI: 10.1039/c7cc05794f

Here we report a set of direct functionalization methods of unmasked 2-phenylquinazolin-4(3 H )-ones, a privileged alkaloid core, without the installation/removal event of protecting groups or exogenous coordinating moieties. Divergent pathways were modulated with transition-metal catalysts by suppressing competitive reactivities, leading to N -arylation, annulative π-extension, or C-H fluorination. An orthogonal reactivity modulation strategy affords diverse synthetic analogues from unmasked quinazolin-4(3 H )-ones.