A versatile and atom-economic three-component reaction between 3-cyano-4-styrylcoumarins, 1,3-indandione, and aliphatic alcohols is described for synthesizing diversely multifunctionalized benzocoumarins. This strategy allows facile access to various benzocoumarins bearing an amine and a substituted benzoyl scaffold under simple heating conditions. Readily available precursors, operational simplicity, acceptable functional group tolerance, and excellent yields are some highlighted advantages of this transformation.