Synthesis of a new class of heterocyclic hybrid embedding spirooxindole, pyrrolidine and chromanone structural moieties was achieved in excellent yield using an intermolecular [3+2]-cycloaddition cascade reaction protocol. The synthesized spiropyrrolidines were unambiguously determined by spectroscopic analysis and the stereo-and regiochemistry of the cycloadducts were undoubtably assigned by single crystal X-ray diffraction analysis. Structural features of the compounds were examined by using X-ray crystallographic studies. The molecular packing was defined by Hirshfeld surface analysis. Furthermore, the structure and reactivity of the synthesized dispiropyrrolidines were investigated by density functional theory (DFT) calculations.