Michael condensation

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.

In this work, the interaction of diarylmethylidene piperidones with acetylacetone and acetoacetic ester has been studied. It has been shown that the transition to piperidone in the basis of dienone does not allow the selective synthesis of products. It has been found that the direction of the reaction with 1,3-C,C-dinucleophilic reagents is infl uenced by the nature of peripheral ylidene substituents, which allows targeted synthesis of O-heterocyclization products (hexahydropyranopyridines) by introducing an NO2 group into the arylmethylidene fragment.