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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

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Abstract

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.

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Acknowledgements

The authors gratefully acknowledge the financial support of the Russian Foundation for Basic Research (Project 18-03-00212).

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Authors and Affiliations

  1. N. D. Zelinsky Institute of Organic Chemistry, Leninsky prospect 47, Moscow, Russian Federation, 119991

    Michail N. Elinson, Anatoly N. Vereshchagin, Yuliya E. Anisina, Stepan K. Krymov, Artem N. Fakhrutdinov & Mikhail P. Egorov

  2. A. N. Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences, Vavilova Str. 28, Moscow, Russian Federation, 119991

    Alexander S. Goloveshkin

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  1. Michail N. Elinson
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Elinson, M.N., Vereshchagin, A.N., Anisina, Y.E. et al. 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. Mol Divers 24, 617–626 (2020). https://doi.org/10.1007/s11030-019-09968-x

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