MILD AND EFFICIENT ADDITION OF CARBON NUCLEOPHILES TO CONDENSED PYRIDINES: INFLUENCE OF STRUCTURE AND LIMITS OF APPLICABILITY

Authors

  • Alexey M. Starosotnikov N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky Ave., Moscow 119991, Russia
  • Kirill V. Ilkov National University of Oil and Gas ''Gubkin University'', 65 Leninsky Ave., Moscow 119991, Russia
  • Maxim A. Bastrakov N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky Ave., Moscow 119991, Russia
  • Ivan V. Fedyanin A. N. Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences, 28 Vavilova St., Moscow 119991, Russia Plekhanov Russian University of Economics, 30 Stremyanny Per., Moscow 117997, Russia
  • Vladimir A. Kokorekin N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky Ave., Moscow 119991, Russia

DOI:

https://doi.org/10.1007/5442

Keywords:

carbon nucleophiles, condensed pyridines, nitrogen heterocycles, dearomatization, nucleophilic addition.

Abstract

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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Published

2020-01-31

Issue

Vol. 56 No. 1 (2020)

Section

Original Papers