A facile synthesis of novel pyridone-annelated spirooxindolepyrrolidines via 1,3-dipolar cycloaddition (original) (raw)
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Mediterranean Journal of Chemistry, 2015
1,3-dipolar cycloaddition of (E)-arylidene-(2H)-indanones 1 (Ar = Ph, p-MeC6H4, p-MeOC6H4, p-ClC6H4, p-NO2C6H4) and (E)-2-arylidene-(2H)-tetralones 2 (Ar = Ph, p-MeC6H4, p-MeOC6H4, p-ClC6H4, p-NO2C6H4) to N-metalated azomethine ylides 3 generated from methyl N-arylideneglycinate in the presence of silver acetate produces in good yields novel methyl 1-oxo-2',4'-diaryl-1,3-dihydrospiro[indene-2,3'-pyrrolidine]-5'-carboxylates 4 and methyl 1-oxo-2',4'-diaryl-3,4-dihydro-1H-spiro[naphthalene-2,3'-pyrrolidine]-5'carboxylates 5. The cycloaddition proceeds in regio-and stereoselective manner (100%) at room temperature to afford respectively the syn-endo cycloadducts 4 and 5 via metallo-azomethine ylides. The regio-and stereochemistry of the spiranic adducts have been established on the basis of spectroscopic data and elemental analysis, corroborated by single-crystal X-ray crystallographic analysis of the heterocycles 4ci, 4bg and 5bi. The endo-pyrrolidines 4 were brominated by N-bromosuccinimide to give finally the dehydrobrominated 3, 4dihydro-2H-pyrrole derivatives 6. The spiro-adducts 4 and their corresponding oxidation products 6 are fluorescent in solution.
A series of spiro[pyrrolidin-2,3 0-oxindoles] has been synthesized by exo-selective 1,3-dipolar cycloaddition reaction of a stabilized azomethine ylide, generated in situ by thermal [1,5]-prototropy, across various (E)-3-arylidene-1-phenyl-pyrrolidine-2,5-diones. The stereochemistry of these N-heterocycles has been confirmed using an X-ray diffraction study. To rationalize the observed regio-and stereoselectivity, DFT calculations at the B3LYP/6-31G(d,p) level were employed. It was found that this reaction preferentially affords the kinetic product. The compounds have been screened for their in vitro antibacterial, antifungal, antimalarial and antitubercular activities. Several compounds exhibited good activities comparable to those of established standard drugs.
Synthesis and characterization of a new spirooxindole grafted pyrrolidino/piperidine moiety
Records of Pharmaceutical and Biomedical Sciences
In this text, we synthesized and characterized a new spirooxindole grafted pyrrolidino/piperidine moieties. The new hit obtained via one-pot reaction of the chalcone based cyclohexanone with the isatin and (R)-piperidine-2-carboxylic acid in MeOH under reflux for 48 h. The compound exclusively obtained in regio-selective and diastereo-selective manner. The chemical feature of the target compound is confirmed by 1 H NMR and 13 C NMR spectroscopy. In addition, we reported for the first time the X-ray single crystal structure of isatin. Its molecular packing depends mainly on strong O…H hydrogen bonds and π-π stacking interactions as well as weak H…H and H…C contacts. Using DFT calculations, isatin is a polar molecule with a net dipole moment of 5.912 Debye. Also, the calculated structure agreed very well with the experimental one. The charge distribution at the different atomic sites is calculated using NBO calculations.