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.