Approaches to the design of new hybrid polyoxaheterocyclic compounds based on the interaction of 2-(4-carboxybenzylidene)-3,4- dihydronaphthalene-1(2H)-one with methylene active compounds of the 2H-chromen-2-one series – 3 -(1,3-dioxobutan-1-yl)-2H-chromen2-one and 4-hydroxy-2H-chromen-2-one, as well as their carbocyclic analogue – 1,3-indanedione under various conditions have been considered.