One-pot three-component reaction of 3-(polyfluoroacyl)chromones with active methylene compounds and ammonium acetate:: regioselective synthesis of novel RF-containing nicotinic acid derivatives

被引：49

作者：

Sosnovskikh, Vyacheslav Ya. ^{[1
]}

Irgashev, Roman A. ^{[1
]}

Kodess, Mikhail I. ^{[2
]}

机构：

[1] Ural State Univ, Dept Chem, Ekaterinburg 620083, Russia

[2] Russian Acad Sci, Ural Branch, Inst Organ Synth, Ekaterinburg 620041, Russia

来源：

TETRAHEDRON | 2008年 / 64卷 / 13期

基金：

俄罗斯基础研究基金会;

关键词：

three-component reactions; 3-(polyfluoroacyl)chromones; active methylene compounds; ammonium acetate; nicotinic acid derivatives;

D O I：

10.1016/j.tet.2008.01.076

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Reactions of 3-(polyfluoroacyl)chromones with acetoacetamide and ethyl acetoacetate in the presence of ammonium acetate proceed at the C-2 atom of the chromone system with pyrone ring-opening and subsequent cyclization to 5-salicyloyl-2-methyl-6-(trifluoromethyl)nicotinamides, ethyl 5-salicyloyl-2-methyl-6-(trifluoromethyl)nicotinates, and ethyl 5-hydroxy-2-methyl-5-(polyfluoroalkyl)-5H-chromeno[4,3-b]pyridine-3-carboxylates. Similar reaction with beta-aminocrotononitrile gave 5-hydroxy-2-methyl-5-(polyfluoroalkyl)-5H-chromeno[4,3-b]pyridine-3-carbonitriles. (C) 2008 Elsevier Ltd. All rights reserved.

引用

页码：2997 / 3004

页数：8

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