Stereoselective synthesis, structure and DFT studies on fluoro- and nitro- substituted spirooxindole-pyrrolidine heterocyclic hybrids

Targeting potential receptor molecules in non-small cell lung cancer (NSCLC) using in silico approaches

“…Figure 2 depicts the theoretically simulated infrared and Raman spectra of the Lochnericine bioactive compound. The experimentally determined vibrational wavenumbers and theoretically calculated vibrational wavenumber values agreed well ( Areans et al, 1988 ; Karabacak et al, 2008 ; Almansouret al, 2021 ). The molecule’s vibrational frequencies were calculated using the VEDA 4.0 programme, which many researchers have recognized as applicable ( Zhou et al, 2021 ).…”

Recent synthetic strategies of spiro-azetidin-2-one, -pyrrolidine, -indol(one) and -pyran derivatives-a review

“…Synthesis of N -allyl-bis(methoxyphenylmethylidene)piperidone ( 127 ), starting with piperidin-4-one·HCl ( 123 ), is outlined in Scheme 31. The spirooxindole-pyrrolidine 128 was extracted in good yield (86%) via the cycloaddition of dipolarophile 127 78 with the azomethine ylide generated in situ from isatin derivatives 71 and sarcosine ( 56 ) at reflux in CH 3 OH for 1 h. The same reaction was performed in [bmim]Br at 100 °C (Scheme 31). TLC analysis of the reaction mixture revealed completion of the reaction in about 30 min with formation of the sole reaction product.…”

“…The reaction in [bmim]Br afforded a slightly better yield (90%) of 128 over the conventional heating employing CH 3 OH (86%) (Scheme 31). 78 Yan's group 79 have described a procedure for the formation of CF 3 -containing spiro-oxindole-pyrrolidinepyrazolone compounds 131 via organo-catalytic [3 + 2] cycloaddition. This reaction involves the cycloaddition of a,b-unsaturated pyrazolones 129 with N-2,2,2-triuoroethylisatin ketimines 130 in CHCl 3 at ambient temperature in the presence of a cinchoninederived squaramide 65 catalyst to produce a pyrrolidine spirofused with both oxindole and pyrazolone (131) with four adjacent stereocenters and two adjacent spiro-quaternary chiral centers, in high efficiencies and stereoselectivities (Scheme 32).…”

Expeditious entry into carbocyclic and heterocyclic spirooxindoles

“…Bismethoxyphenylmethylidene-piperidone 104 undergoes a 1,3-dipolar cycloaddition reaction with azomethine ylides generated from isatin 5 and N -methylglycine 105 in the presence of [bmim]Br, an ionic liquid, as the solvent (Scheme 66). 59 Two spirooxindoles 106 were isolated in excellent yields. Molecular packing was analyzed via Hirshfeld calculations and confirmed the predominant H⋯H, O⋯H and H⋯C(π) interactions in the crystal structure.…”