A ruthenium(II)-catalyzed cyclization of benzimidates with substituted propargyl alcohols to provide 3,4-disubstituted 1-alkoxy isoquinolines in a highly selective manner via the C-H allenylation is described. The proposed reaction mechanism of the ruthenium(II)-catalyzed cyclization reaction is strongly supported by the isolation of the key ruthenacycle intermediate, deuterium-labeling studies, and detailed DFT calculations including the transition states. © 2018 American Chemical Society.