Design, synthesis, structural characterization and computational studies of new class of dispirooxindolopyrrolidine embedded chromanone hybrid heterocycles

• Published in: Journal of molecular structure 2023-08, Vol.1286, p.135539, Article 135539
• Main Authors: Arumugam, Natarajan, Alkaltham, Manal Fahad, Viswanathan, Vijayan, Almansour, Abdulrahman I., Kumar, Raju Suresh, Alaqeel, Shatha Ibrahim, Kumar, Santhakumar Yeswant, Padmanaban, Ramanathan, Mahalingam, Sakkarapalayam M., Dege, Necmi
• Format: Article
• Language: English
• Subjects: [3+2]-Cycloaddition methodology; Computational study; Single crystal X-ray diffraction study; Spirooxindolopyrrolidines
• ISSN: 0022-2860; 1872-8014
• DOI: 10.1016/j.molstruc.2023.135539

•Spiropyrrolidine embedded chromanones were achieved in excellent yield.•Spiropyrrolidines were synthesized using one-pot cycloaddition methodology.•Compounds unambiguously assigned by spectroscopic and single crystal XRD analysis.•Structural determination of the compounds was investigated by computational study. 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.