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• Synthesis of a structurally unexplored novel class of ferrocene fused spiropyrrolidine hybrid. • Spiro compound was achieved in excellent yield via a one-pot multicomponent cascade protocol. • The synthesized compound was elucidated by spectroscopic, X-ray diffraction and computational studies. • Spirocompound displayed significant activity against tested MDR S. aureus strains. Our synthetic approach for the assembly of highly diversified spiropyrrolidine grafted ferrocene was based on a one-pot four component cascade reaction protocol involving 1,3-dipolar cycloaddition reaction of (E)-3-ferrocene-1-(4-bromophenyl)prop‑2-en-1-one and azomethine ylide generated in situ from quinoxalinone and l -tryptophan. The structure of the compound was assigned by one- and two-dimensional NMR spectroscopic studies. The regio- and stereochemistry of the spirocompound was confirmed by single crystal X-ray diffraction analysis. The nature of three-dimensional orientation of the synthesized compound has been investigated through single crystal X-ray diffraction study. Crystal structure of the synthesized compound was analyzed using Hirshfeld calculations. In spirocompound, the packing of molecules is controlled by significant O...H (3.3%), N...H (4.1%) and C H...π (24.8%) interactions. The different π-donation and π-back donation interactions was analysed using NBO calculations. The compound 6 exhibited potent inhibitory activity against tested MDR S. aureus strains ranging from 8.00 to 256.00 µg/mL with respect to MIC and MBC determination. [ABSTRACT FROM AUTHOR]

• Dispiropyrrolidines synthesized in excellent yield via cycloaddition strategy. • Compounds were elucidated by spectroscopic and single crystal X-ray analysis. • Molecular packing and structure reactivity descriptors were investigated. • Compounds assayed for their antimicrobial activity against K. pneumonia strains. • Antimicrobial efficacy was also performed through molecular docking study. A regio and stereoselective synthesis of a new class of spirooxindolopyrrolidine embedded indandione heterocycles was obtained in excellent yield employing a three-component cascade reaction protocol. The key step for this protocol is a 1,3-dipolar cycloaddition reaction involving azomethine ylide generated in situ from isatin and l -phenylalanine. The structure of newly synthesized compound was assigned based on the NMR spectroscopic analysis and the stereo/regiochemistry was undoubtable assigned by single crystal X-ray diffraction analysis. Further, the structural determination of the compound was assigned through density functional theory (DFT) and Hirshfeld surface analysis. It is found that the compound was highly stabilized by intermolecular interactions such as X-H-H-X (X = C and O) and also by hydrogen bonding interaction. The synthesized compounds were assayed for their antibacterial activity against five different clinical bacterial strains of K. pneumoniae and found that the compound possessing chloro‑substitution on aryl ring showed significant activity against tested K. pneumoniae strains. [Display omitted] [ABSTRACT FROM AUTHOR]

• Synthesis of structurally intriguing fused pyrroloquinoline hybrid heterocycle in excellent yield. • Compound was achieved via one-pot cascade protocol under eco-friendly solvent free condition. • Compound was assigned by spectroscopic and single crystal X-ray diffraction analysis. • Molecular packing and structure reactivity descriptors were investigated via computational studies. • Compound showed significant antimicrobial activity against tested bacterial and fungal pathogens. Synthesis of a structurally complex hitherto unexplored novel class of pyrene fused pyrroloquinolinone was achieved in excellent yield via an environmental friendly solid-state melt reaction condition employing multicomponent cascade protocol which involves 1,3-dipolar cycloaddition and subsequent double annulation process. The 1,3-dipole component was derived in situ from diketone and α-amino acid, whereas the Baylis-Hillman adduct synthesized from pyrene-1-carbaldehyde was utilized as a dipolarophile. Structure of the compound was elucidated by 1H and 13C NMR spectroscopic analysis and further confirmed through single crystal X-ray diffraction and the molecular packing was described by using Hirshfeld surface analysis. The structure-reactivity descriptors of the synthesized compound were examined through DFT calculations. The pyrroloquinoline was evaluated for its antibacterial activity against three multi drug resistant bacterial and two fungal pathogens. The MIC value of the tested microbial pathogens were exhibited with minimum (0.156 mg/mL) and maximum (1.250 mg/mL). The antimicrobial results disclosed that compound 6 is considered as a potent candidate for effective therapeutic applications. [ABSTRACT FROM AUTHOR]