Pot, atom and step economic (PASE) assembly of salicylaldehydes, malononitrile dimer and 4-hydroxypyridine-2(1H)-ones into medicinally relevant 5H-chromeno[2,3-b]pyridine scaffold

Pot, atom and step economic (PASE) assembly of salicylaldehydes, malononitrile dimer and 4-hydroxypyridine-2(1H)-ones into medicinally relevant 5H-chromeno[2,3-b]pyridine scaffold Full article

Journal

Molecular Diversity
ISSN: 1573-501X , E-ISSN: 1381-1991

Output data

Year: 2020, Volume: 24, Number: 3, Pages: 617-626 Pages count : 10 DOI: 10.1007/s11030-019-09968-x

Authors

Elinson Michail N. ¹ , Vereshchagin Anatoly N. ¹ , Anisina Yuliya E. ¹ , Krymov Stepan K. ¹ , Fakhrutdinov Artem N. ¹ , Goloveshkin Alexander S. ² , Egorov Mikhail P. ¹

Affiliations

1	N. D. Zelinsky Institute of Organic Chemistry, Leninsky prospect 47, Moscow, Russian Federation 119991
2	A. N. Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences, Vavilova Str. 28, Moscow, Russian Federation 119991

The new multicomponent reaction (MCR) has been found: one-pot selective and efficient formation of the new 5-(4-hydroxy-2-oxo-1,2-dihydropyridin-3-yl)-substituted 5H-chromeno[2,3-b]pyridines in 61–97% yields directly from simple and easily available salicylaldehydes, malononitrile dimer and 4-hydroxypyridine-2(1H)-ones in small amount of pyridine–ethanol catalyst/solvent system. This complex “domino” transformation includes Knoevenagel condensation of salicylaldehyde with malononitrile dimer, Michael addition of 4-hydroxypyridine-2(1H)-one, double Pinner-type reaction cyclization and isomerization with following protonation. This facile multicomponent process opens a new way to 5-(4-hydroxy-2-oxo-1,2-dihydropyridin-3-yl)-substituted 5H-chromeno[2,3-b]pyridine systems, which are promising compounds for the treatment for human inflammatory TNFα-mediated diseases and different biomedical applications.

Elinson M.N. , Vereshchagin A.N. , Anisina Y.E. , Krymov S.K. , Fakhrutdinov A.N. , Goloveshkin A.S. , Egorov M.P.
Pot, atom and step economic (PASE) assembly of salicylaldehydes, malononitrile dimer and 4-hydroxypyridine-2(1H)-ones into medicinally relevant 5H-chromeno[2,3-b]pyridine scaffold
Molecular Diversity. 2020. V.24. N3. P.617-626. DOI: 10.1007/s11030-019-09968-x WOS Scopus OpenAlex

Web of science:	WOS:000547921900003
Scopus:	2-s2.0-85066975642
OpenAlex:	W2951415667

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OpenAlex	12
Scopus	9
Web of science	11