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

被引:27
作者
Elinson, Michail N. [1 ]
Vereshchagin, Anatoly N. [1 ]
Anisina, Yuliya E. [1 ]
Fakhrutdinov, Artem N. [1 ]
Goloveshkin, Alexander S. [2 ]
Egorov, Mikhail P. [1 ]
机构
[1] Russian Acad Sci, ND Zelinsky Inst Organ Chem, 47 Leninsky Prospekt, Moscow 119991, Russia
[2] Russian Acad Sci, AN Nesmeyanov Organoelement Cpds Inst, Moscow, Russia
基金
俄罗斯基础研究基金会;
关键词
Multicomponent reactions; Synthesis design; Reaction mechanisms; Phosphonates; SOLVENT-FREE; PHARMACOLOGICAL EVALUATION; EFFICIENT APPROACH; ORGANIC-SYNTHESIS; ON-WATER; MALONONITRILE; FACILE; ACID; SALICYLALDEHYDES; DERIVATIVES;
D O I
10.1002/ejoc.201900240
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
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.
引用
收藏
页码:4171 / 4178
页数:8
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