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

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

Journal

Chemistry of Heterocyclic Compounds
ISSN: 1573-8353 , E-ISSN: 0009-3122

Output data

Year: 2020, Volume: 56, Number: 1, Pages: 92-100 Pages count : 9 DOI: 10.1007/s10593-020-02628-1

Authors

Starosotnikov Alexey M. ¹ , Ilkov Kirill V. ² , Bastrakov Maxim A. ¹ , Fedyanin Ivan V. ^3,4 , Kokorekin Vladimir A. ¹

Affiliations

1	N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Moscow, Russia
2	National University of Oil and Gas “Gubkin University”, Moscow, Russia
3	A. N. Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences, Moscow, Russia
4	Plekhanov Russian University of Economics, Moscow, Russia

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.

Starosotnikov A.M. , Ilkov K.V. , Bastrakov M.A. , Fedyanin I.V. , Kokorekin V.A.
Mild and efficient addition of carbon nucleophiles to condensed pyridines: influence of structure and limits of applicability
Chemistry of Heterocyclic Compounds. 2020. V.56. N1. P.92-100. DOI: 10.1007/s10593-020-02628-1 WOS Scopus OpenAlex

Web of science:	WOS:000516389100001
Scopus:	2-s2.0-85079803258
OpenAlex:	W3004814786

DB	Citing
OpenAlex	15
Scopus	14
Web of science	12