Metal-Free Michael-Addition-Initiated Three-Component Reaction for the Regioselective Synthesis of Highly Functionalized Pyridines: Scope, Mechanistic Investigations and Applications

被引：56

作者：

Allais, Christophe ^{[1
]}

Lieby-Muller, Frederic ^{[1
]}

Rodriguez, Jean ^{[1
]}

Constantieux, Thierry ^{[1
]}

机构：

[1] Aix Marseille Univ, CNRS, UMR 7313 iSm2, F-13397 Marseille, France

来源：

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2013年 / 2013卷 / 19期

关键词：

Nitrogen heterocycles; Multicomponent reactions; Michael addition; Reaction mechanisms; Heterogeneous catalysis; ONE-POT SYNTHESIS; MULTICOMPONENT DOMINO REACTION; ENANTIOSELECTIVE SYNTHESIS; 1,3-DICARBONYL COMPOUNDS; 1,3,5-TRISUBSTITUTED PYRAZOLINES; HANTZSCH 1,4-DIHYDROPYRIDINES; POLYSUBSTITUTED PYRIDINES; OXIDATIVE AROMATIZATION; SUBSTITUTED PYRIDINES; EFFICIENT ACCESS;

D O I：

10.1002/ejoc.201300246

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A metal-free and completely regioselective three-component synthesis of highly functionalized pyridines from 1,3-dicarbonyl derivatives and Michael acceptors has been achieved. Activated Michael acceptors, that is, ,-unsaturated -oxo carbonyl derivatives, were utilized, allowing substitution at the 4-position and remarkable functional diversity at the 2-position of the pyridine ring. The scope and limitations of this environmentally friendly domino reaction are disclosed, with full experimental data, and the results of mechanistic investigations are discussed.

引用

页码：4131 / 4145

页数：15

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