The one-pot synthesis of benzo[f]quinolin-3-ones and benzo[a]phenanthridein-5-ones was achieved by the inter- and intramolecular photoannulation of 6-chloropyridin-2-ones and 3-chloroisoquinolin-1-ones with phenylacetylene or tethered phenylacetylene. The reactions were proceeded by photoaddition of 6-chloropyridin-2-ones and 3-chloroisoquinolin-1-ones to phenylacetylene to give the chlorine-substituted stilbenoids, and then 6π electrocyclization of the stilbenoids and oxidation aromatization to afford the polycyclic products.