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Pot‐, Atom‐ and Step‐Economic (PASE) Multicomponent Approach to the 5‐(Dialkylphosphonate)‐Substituted 2,4‐Diamino‐5 H ‐chromeno[2,3‐ b ]pyridine Scaffold
Author(s) -
Elinson Michail N.,
Vereshchagin Anatoly N.,
Anisina Yuliya E.,
Fakhrutdinov Artem N.,
Goloveshkin Alexander S.,
Egorov Mikhail P.
Publication year - 2019
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201900240
Subject(s) - chemistry , malononitrile , pyridine , combinatorial chemistry , phosphonate , dimer , medicinal chemistry , reaction conditions , stereochemistry , organic chemistry , catalysis
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‐5 H ‐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‐5 H ‐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.