Azomethine Ylide

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A V Stepakov - One of the best experts on this subject based on the ideXlab platform.

  • stereo and regioselective 1 3 dipolar cycloaddition of the stable ninhydrin derived Azomethine Ylide to cyclopropenes trapping of unstable cyclopropene dipolarophiles
    Journal of Organic Chemistry, 2019
    Co-Authors: Alexander S Filatov, Anna G Larina, Vitali M Boitsov, A V Stepakov, Siqi Wang, Olesya V. Khoroshilova, Stanislav V. Lozovskiy
    Abstract:

    A stereo- and regioselective 1,3-dipolar cycloaddition of the stable ninhydrin-derived Azomethine Ylide [2-(3,4-dihydro-2H-pyrrolium-1-yl)-1-oxo-1H-inden-3-olate, DHPO] to differently substituted c...

  • Stereo- and Regioselective 1,3-Dipolar Cycloaddition of the Stable Ninhydrin-Derived Azomethine Ylide to Cyclopropenes: Trapping of Unstable Cyclopropene Dipolarophiles
    2019
    Co-Authors: Alexander S. Filatov, Anna G Larina, Vitali M Boitsov, Siqi Wang, Olesya V. Khoroshilova, Stanislav V. Lozovskiy, A V Stepakov
    Abstract:

    A stereo- and regioselective 1,3-dipolar cycloaddition of the stable ninhydrin-derived Azomethine Ylide [2-(3,4-dihydro-2H-pyrrolium-1-yl)-1-oxo-1H-inden-3-olate, DHPO] to differently substituted cyclopropenes has been established. As a result, an efficient synthetic protocol was developed for the preparation of biologically relevant spiro­[cyclopropa­[a]­pyrrolizine-2,2′-indene] derivatives. DHPO has proved to be an effective trap for such highly reactive and unstable substrates as parent cyclopropene, 1-methylcyclopropene, 1-phenylcyclopropene, and 1-halo-2-phenylcyclopropenes. It has also been found that 3-nitro-1,2-diphenylcyclopropene undergoes a nucleophilic substitution reaction in alcohols and thiols to afford 3-alkoxy- and 3-arylthio-substituted 1,2-diphenylcyclopropenes, which can be captured as corresponding 1,3-dipolar cycloadducts in the presence of DHPO. These new approaches provide a straightforward strategy for the synthesis of functionally substituted cyclopropa­[a]­pyrrolizine derivatives. The factors governing regio- and stereoselectivity have been revealed by means of quantum mechanical calculations (M11 density functional theory), including previously unreported NYlide–Hcyclopropene second-orbital interactions. The outcome of this work contributes to the study of 1,3-dipolar cycloaddition, as well as enriches chemistry of cyclopropenes and methods for the construction of polycyclic compounds with cyclopropane fragments

  • synthesis of functionalized 3 spiro cyclopropa a pyrrolizine and 3 spiro 3 azabicyclo 3 1 0 hexane oxindoles from cyclopropenes and Azomethine Ylides via 3 2 cycloaddition
    Journal of Organic Chemistry, 2017
    Co-Authors: Alexander S Filatov, Nickolay A Knyazev, A P Molchanov, Taras L Panikorovsky, R R Kostikov, Anna G Larina, Vitali M Boitsov, A V Stepakov
    Abstract:

    3-Spiro[cyclopropa[a]pyrrolizine]- and 3-spiro[3-azabicyclo[3.1.0]hexane]oxindoles were prepared in moderate to high yields via one-pot three-component reactions using substituted isatins, α-amino acids, and cyclopropenes. The key step is an intramolecular [3 + 2]-cycloaddition reaction of an in situ generated Azomethine Ylide onto a cyclopropene. Both N-substituted and N-unsubstituted α-amino acids, dipeptide Gly-Gly, and also benzylamine were used as the amine component for the Azomethine Ylide generation. The anticancer activity of some of the obtained compounds against human leukemia K562 cell line was evaluated by flow cytometry in vitro.

  • Synthesis of Functionalized 3‑Spiro[cyclopropa[a]pyrrolizine]- and 3‑Spiro[3-azabicyclo[3.1.0]hexane]oxindoles from Cyclopropenes and Azomethine Ylides via [3 + 2]-Cycloaddition
    2016
    Co-Authors: Alexander S. Filatov, Nickolay A Knyazev, A P Molchanov, Taras L Panikorovsky, R R Kostikov, Anna G Larina, Vitali M Boitsov, A V Stepakov
    Abstract:

    3-Spiro­[cyclopropa­[a]­pyrrolizine]- and 3-spiro­[3-aza­bicyclo­[3.1.0]­hexane]­oxindoles were prepared in moderate to high yields via one-pot three-component reactions using substituted isatins, α-amino acids, and cyclopropenes. The key step is an intramolecular [3 + 2]-cycloaddition reaction of an in situ generated Azomethine Ylide onto a cyclopropene. Both N-substituted and N-unsubstituted α-amino acids, dipeptide Gly-Gly, and also benzylamine were used as the amine component for the Azomethine Ylide generation. The anticancer activity of some of the obtained compounds against human leukemia K562 cell line was evaluated by flow cytometry in vitro

Raghavachary Raghunathan - One of the best experts on this subject based on the ideXlab platform.

Hongchao Guo - One of the best experts on this subject based on the ideXlab platform.

Vladimir S Moshkin - One of the best experts on this subject based on the ideXlab platform.

Vyacheslav Ya. Sosnovskikh - One of the best experts on this subject based on the ideXlab platform.