Synthesis of 3′H-cyclopropa[1,9](C60-I h)[5,6]fullerenes from 2′-aryl-1′,1′-dimethyl-2′,5′-dihydro-1′H-pyrrolo[3′,4′:1,9]-(C60-I h)[5,6]fulleren-1-ium iodides

Russian Journal of Organic Chemistry - New 1′,1′-dimethyl-2′,5′-dihydro-1′H-pyrrolo[3′,4′:1,9](C60-I h)[5,6]fulleren-1-ium iodides containing different...     

A facile regio- and stereoselective synthesis of novel dispirooxindolyl-[acridine-2′,3-pyrrolidine/thiapyrrolizidine]-1′-ones via 1,3-dipolar cycloaddition of azomethine ylides

A facile regio- and stereoselective synthesis of novel dispirooxindolyl-[acridine-2′,3-pyrrolidine]-1′-ones and dispirooxindolyl-[acridine-2′,3-thiapyrrolizidine]-1′-ones have been accomplished via 1,3-dipolar cycloaddition of azomethine ylides, generated in situ from the reaction of sarcosine/1,3-thiazolane-4-carboxylic acid and substituted isatins, to a series of (E)-2-[arylmethylidene]-3,4-dihydro-1(2H)-acridinones in good yields.     

Optically active diastereomers of N-methyl-1??-(?)-myrtenylpyrrolidino[3??,4??:1,9](C60-J h)[5,6]fullerenes: synthesis, electrochemical and chiroptical properties

Novel optically active diastereomers of N-methyl-1??-myrtenylpyrrolidino[3??,4??:1,9]-(C₆₀-J _h)[5,6]fullerenes were synthesized. Reaction of the latter with methyl iodide yielded the corresponding quaternary ammonium salts. Individual diastereomers were isolated, their chiroptical and electrochemical properties were studied.     

A facile regio- and stereoselective synthesis of novel spiro[indolin-3,2′-pyrrolidin]-2-one’s via 1,3-dipolar cycloaddition of azomethine ylides

A facile regio and stereoselective synthesis of novel spiro[indolin-3,2′-pyrrolidin]-2-one’s have been accomplished through 1,3-dipolar cycloaddition of azomethine ylides generated in situ from the reaction of isatin and benzyl amine with quinoline bearing dipolarophiles in good yields. The synthesized compounds were well characterized through different spectroscopic techniques, such as single crystal XRD, FTIR, NMR, and mass spectral analysis.     

Diastereoselective synthesis of diverse 3,2′-pyrrolidinyl bispirooxindoles via 1,3-dipolar cycloaddition reactions of azomethine ylides with exocyclic α,β-unsaturated ketones and in silico studies for prediction of bioactivity

A three-component highly regio- and diastereoselective 1,3-dipolar cycloaddition reaction between isatin, a series of primary amino acids (10 nos), and exocyclic α,β-unsaturated ketones was developed towards the synthesis of a small library of bispirooxindole (20 nos) at ambient temperature. The developed reaction afforded highly substituted 3,2′-pyrrolidine-bispirooxindole with two vicinal spiro-quaternary and four contiguous stereocenters from the cheap and abundant starting materials. The products were obtained with good to excellent yields (50–95%) and as a single diastereoisomer in the majority of the cases. Primary amino acids were served as amine component for the in-situ generation of azomethine ylides from isatin. Molecular docking studies were carried out to explore the synthesized bispirooxindoles as inhibitors of the epidermal growth factor receptor (EGFR). Two compounds exhibited excellent binding affinity towards EGFR receptor.     

Stereoselective [π4s+π2s]-dipolar cycloaddition of pyridinium ylides to nitriles of the trans-1,3-butadiene series. Crystal and molecular structure of 3-benzoyl-1-(2,2-dicyano-1-cyclopropylvinyl)-2-phenyl-6-cyano-1,2-trans-2,3-trans-1,9-trans-1,2,3,9-tetrahydroindolizine

The interaction of substituted trans-1,1-dicyano-4-phenyl-1,3-butadienes with pyridinium ylides proceeds through the path of [4_s+2_s]-dipolar cycloaddition, highly regioselective and stereoselective, with the formation of substituted 1-(2,2-dicyanovinyl)-2-phenyl-6-cyano-1,2-trans-2,3-trans-1,9-trans-1,2,3,9-tetrahydroindolizines. The stereoselectivity of these reactions is due to endo-addition of molecules of trans-1,3-butadienes to the anti form of the pyridinium ylides; it is confirmed by correlation analysis of the data from double PMR, mathematical calculations of torsion angles, and x-ray structural studies of the substituted tetrahydroindolizines.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 10, pp. 1354–1360, October, 1991.     

Cobalt(II) porphyrin axially coordinated with 2′-(pyridin-4-yl)-5′-(pyridin-2-yl)-1′-(pyridin-2-ylmethyl)-2′,4′-dihydro-1′H-pyrrolo[3′,4′ : 1,2](C60-Ih)[5,6]fullerene: formation,chemical structure,and spectroscopic properties

Construction of new effective photovoltaic devices based on organic dyes has important implications for modern and future technologies. In this article, we studied the equilibrium, the rate, and the spectral manifestation of the reaction of [(2,3,7,8,12,18-hexamethyl,13,17-diethyl,5-(2-pyridyl)porphyrinato)cobalt(II)]–[2′-(pyridin-4-yl)-5′-(pyridin-2-yl)-1′-(pyridin-2-ylmethyl)-2′,4′-dihydro-1′H-pyrrolo[3′,4′ : 1,2](C₆₀-I_h)[5,6]fullerene] triad formation as well as its spectral properties and photo electrochemical behavior. The cobalt porphyrin–pyridyl-substituted fullerene mixtures in toluene are self-assembling systems due to axial donor–acceptor binding between Co of the porphyrin complex and N-pyridyl of the substituted fullerene. The formation rate constant, k^298K, and the stability constant, K^298K, of donor–acceptor triad formed by coordination of two substituted fullerene molecules to Co porphyrin are (44.4 ± 0.8) mol L^?1 s^?1 and (56 ± 16)×10⁷ L² mol^?2, respectively. Modification of the titanium electrode coated with the natural oxide film was carried out using the porphyrin–fullerene triad and its individual components. Photopotential and photocurrent density of the system with modified electrode were studied. The obtained results are of interest for creating porphyrin-based donor–acceptor systems as components in organic photovoltaics.