Pot‐, Atom‐ and Step‐Economic (PASE) Multicomponent Approach to the 5‐(Dialkylphosphonate)‐Substituted 2, 4‐Diamino‐5H‐chromeno[2, 3‐b]pyridine Scaffold. Issue 26 (25th April 2019)

• Record Type: Journal Article
• Authors: Elinson, Michail N.; Vereshchagin, Anatoly N.; Anisina, Yuliya E.; Fakhrutdinov, Artem N.; Goloveshkin, Alexander S.; Egorov, Mikhail P.
• Other Names: Nifantiev Nikolay E. guestEditor.; Belen'kii Leonid I. guestEditor.; Petrosyan Vladimir A. guestEditor.
• Is Part Of: European journal of organic chemistry. Issue 26(2019)
• Page Start: 4171
• Page End: 4178
• Publication Date: 2019-04-25
• Subjects: Multicomponent reactions -- Synthesis design -- Reaction mechanisms -- Phosphonates; Chemistry, Organic -- Periodicals; Organic compounds -- Synthesis -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1002/ejoc.201900240
• Languages: English
• ISSNs: 1434-193X

Abstract

Abstract : 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. Abstract : The multicomponent reaction of salicylaldehydes, 2‐aminoprop‐1‐ene‐1, 1, 3‐tricarbonitrile, and trialkylphosphites leads to dialkyl (2, 4‐diamino‐3‐cyano‐5 H ‐chromeno[2, 3‐ b ]pyridin‐5‐yl)phosphonates, promising compounds in biomedical applications. This is a new pot‐, atom‐, and step‐economic (PASE) approach to the 5‐(dialkylphosphonate) substituted 2, 4‐diamino‐5 H ‐chromeno[2, 3‐ b ]pyridine scaffold.