A novel and efficient palladium-catalyzed cascade cyclization to indoloquinoline derivatives in one pot has been developed by using allenamide derivatives and 2-iodoanilines as the key building blocks. The process involved two cyclizations: intramolecular cyclization/π-allylic substitution and intramolecular 6-endo Heck cyclization. Furthermore, dihydrobenzofuro[2,3-b]quinoline derivatives could also be achieved via this strategy using allenyl ethers instead of allenamides. The readily available substrates, mild conditions, high efficiency and step economy make this strategy a promising method in the synthesis of polycyclic motifs.