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Mild and efficient addition of carbon nucleophiles to condensed pyridines: influence of structure and limits of applicability

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Chemistry of Heterocyclic Compounds Aims and scope

A number of azolo- and azinopyridines with varying substituents and annulated heterocycles were synthesized and examined in dearomatization reactions with carbon nucleophiles. Depending on the structure, the resulting covalent σ-adducts were formed either under basefree conditions or in Et3N-promoted process to give functionalized condensed dihydropyridines. Quantum-chemical calculations of the global electrophilicity index derived from FMO energies of azolopyridine series were performed to explain reactivity toward neutral and anionic C-nucleophiles. These values may be useful for qualitative prediction of particular reactivity pattern.

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Authors and Affiliations

  1. N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky Ave., Moscow, 119991, Russia

    Alexey M. Starosotnikov, Maxim A. Bastrakov & Vladimir A. Kokorekin

  2. National University of Oil and Gas “Gubkin University”, 65 Leninsky Ave., Moscow, 119991, Russia

    Kirill V. Ilkov

  3. A. N. Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences, 28 Vavilova St., Moscow, 119991, Russia

    Ivan V. Fedyanin

  4. Plekhanov Russian University of Economics, 30 Stremyanny Per., Moscow, 117997, Russia

    Ivan V. Fedyanin

Authors
  1. Alexey M. Starosotnikov
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  2. Kirill V. Ilkov
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  3. Maxim A. Bastrakov
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  4. Ivan V. Fedyanin
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  5. Vladimir A. Kokorekin
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Correspondence to Alexey M. Starosotnikov.

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Published in Khimiya Geterotsiklicheskikh Soedinenii, 2020, 56(1), 92–100

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This work was supported by the Russian Science Foundation (grant 19-73-20259). X-ray diffraction studies were performed with financial support from the Ministry of Science and Higher Education of the Russian Federation using the equipment of the Center for molecular composition studies of the A. N. Nesmeyanov Institute of Organoelement Compounds of the Russian Academy of Sciences.

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Starosotnikov, A.M., Ilkov, K.V., Bastrakov, M.A. et al. Mild and efficient addition of carbon nucleophiles to condensed pyridines: influence of structure and limits of applicability. Chem Heterocycl Comp 56, 92–100 (2020). https://doi.org/10.1007/s10593-020-02628-1

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