One-Pot Synthesis of 1,2-Dihydropyridines: Expanding the Diverse Reactivity of Propargyl Vinyl Ethers

被引：68

作者：

Harschneck, Tobias

Kirsch, Stefan F. ^{[1
]}

机构：

[1] Tech Univ Munich, Dept Chem, D-85747 Garching, Germany

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2011年 / 76卷 / 07期

关键词：

AMINO-CLAISEN REARRANGEMENT; HOMOGENEOUS GOLD CATALYSIS; GOLD(I)-CATALYZED SYNTHESIS; FUNCTIONALIZED PYRROLES; 3-COMPONENT SYNTHESIS; EFFICIENT SYNTHESIS; ORIENTED STRATEGY; CASCADE REACTIONS; DOMINO REACTIONS; FORMAL SYNTHESIS;

D O I：

10.1021/jo102545m

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The catalyzed synthesis of 1,2-dihydropyridines starting from easily accessible propargyl vinyl ethers was realized. The reaction sequence involving a transition metal-catalyzed propargyl-Claisen re-arrangement; a condensation step, and a Bronsted acid-catalyzed heterocyclization furnishes the highly substituted heterocycles in moderate to excellent yields. Additionally, a practical one-pot protocol toward 1,2-dihydropyridines and 2H-pyrans starting from propargylic alcohols was developed.

引用

页码：2145 / 2156

页数：12

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