Pot‐, Atom‐ and Step‐Economic (PASE) Multicomponent Approach to the 5‐(Dialkylphosphonate)‐Substituted 2,4‐Diamino‐5H‐chromeno[2,3‐b]pyridine Scaffold

Pot‐, Atom‐ and Step‐Economic (PASE) Multicomponent Approach to the 5‐(Dialkylphosphonate)‐Substituted 2,4‐Diamino‐5H‐chromeno[2,3‐b]pyridine Scaffold Full article

Journal

European Journal of Organic Chemistry
ISSN: 1434-193X , E-ISSN: 1099-0690

Output data

Year: 2019, Volume: 2019, Number: 26, Pages: 4171-4178 Pages count : 8 DOI: 10.1002/ejoc.201900240

Authors

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

Affiliations

1	N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky Prospekt, 119991 Moscow, Russia
2	A. N. Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences, Moscow, Russia

A new multicomponent reaction is reported: the one-pot transformation of salicylaldehydes, 2-aminoprop-1-ene-1,1,3-tricarbonitrile (malononitrile dimer), and trialkylphosphites results in the efficient formation of (2,4-diamino-3-cyano-5H-chromeno[2,3-b]pyridin-5-yl)phosphonates. The scope of this one-pot reaction was investigated. The isolation of substituted phosphonates is very easy. The optimized reaction conditions and a mechanistic rationale for the complex multicomponent transformation are presented. This facile PASE approach offers a powerful tool for the selective formation of new types of functionalized 5-P-substituted 2,4-diamino-5H-chromeno[2,3-b]pyridine scaffolds containing the phosphonate fragment, which are promising compounds for various biomedical applications, among them the treatment of human inflammatory diseases and cancer therapy.

Elinson M.N. , Vereshchagin A.N. , Anisina Y.E. , Fakhrutdinov A.N. , Goloveshkin A.S. , Egorov M.P.
Pot‐, Atom‐ and Step‐Economic (PASE) Multicomponent Approach to the 5‐(Dialkylphosphonate)‐Substituted 2,4‐Diamino‐5H‐chromeno[2,3‐b]pyridine Scaffold
European Journal of Organic Chemistry. 2019. V.2019. N26. P.4171-4178. DOI: 10.1002/ejoc.201900240 WOS Scopus OpenAlex

Web of science:	WOS:000475679400010
Scopus:	2-s2.0-85065194841
OpenAlex:	W2929564315

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OpenAlex	25
Scopus	27