Potassium fluoride catalysed multicomponent approach to medicinally privileged 5-[3-hydroxy-6-(hydroxymethyl)-4H-pyran-2-yl] substituted chromeno[2,3-b]pyridine scaffold

Potassium fluoride catalysed multicomponent approach to medicinally privileged 5-[3-hydroxy-6-(hydroxymethyl)-4H-pyran-2-yl] substituted chromeno[2,3-b]pyridine scaffold Full article

Journal

Arkivoc
ISSN: 1551-7012 , E-ISSN: 1551-7004

Output data

Year: 2019, Volume: 2019, Number: 2, Pages: 38-49 Pages count : 12 DOI: 10.24820/ark.5550190.p011.002

Authors

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

Affiliations

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

The new efficient and facile multicomponent reaction was found: transformation of salicylaldehydes, kojic acid, and malononitrile dimer in the presence of potassium fluoride as catalyst in small amount of i-propanol results in formation of substituted 2,4-diamino-5-(3-hydroxy-6-(hydroxymethyl)-4-oxo-4H-pyran-2-yl)-5Hchromeno[2,3-b]pyridine-3-carbonitriles in 56-93% yields. This complex “domino” transformation includes Knoevenagel condensation of salicylaldehyde with malononitrile dimer, Michael addition of kojic acid, double Pinner type reaction cyclization, and isomerization with following protonation. The novel ‘one-pot’ process opens an efficient and convenient way to functionalized 5H-chromeno[2,3-b]pyridine systems, which are promising compounds for different biomedical applications.

Elinson M.N. , Vereshchagin A.N. , Anisina Y.E. , Krymov S.K. , Fakhrutdinov A.N. , Egorov M.P.
Potassium fluoride catalysed multicomponent approach to medicinally privileged 5-[3-hydroxy-6-(hydroxymethyl)-4H-pyran-2-yl] substituted chromeno[2,3-b]pyridine scaffold
Arkivoc. 2019. V.2019. N2. P.38-49. DOI: 10.24820/ark.5550190.p011.002 Scopus OpenAlex

Scopus:	2-s2.0-85079035980
OpenAlex:	W2976106692

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