The Ru(ii)-catalyzed tunable [5+1]/[5+2] annulation of N-benzo[d]imidazole indolines with propargyl carbonates has been realized for the divergent synthesis of ring-fused quinazolines and 1,3-benzodiazepines bearing various functional groups. These transformations represent an efficient and practical strategy in constructing complex heterocycles via diversified C-H functionalization. A distinctive acidity-controlled reaction manner has been clarified to account for the chemoselectivity.