Regioselective Synthesis of 6-Vinyl-3,6-dihydropyridine-2(1H)-ones through Simple Addition of a Vinylmagnesium "Ate" Complex to 2-Pyridones

被引：11

作者：

Sosnicki, Jacek G. ^{[1
]}

Dzitkowski, Przemyslaw ^{[1
]}

Struk, Lukasz ^{[1
]}

机构：

[1] West Pomeranian Univ Technol, Inst Chem & Environm Protect, PL-71065 Szczecin, Poland

来源：

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2015年 / 2015卷 / 23期

关键词：

Nucleophilic addition; Nitrogen heterocycles; Lactams; Magnesium; Substituent effects; HIGHLY STEREOSELECTIVE-SYNTHESIS; DELTA-LACTAMS; ASYMMETRIC-SYNTHESIS; LITHIUM ALLYLDIBUTYLMAGNESATE; ENANTIOSELECTIVE SYNTHESIS; REDUCTIVE ALKYLATION; EFFICIENT SYNTHESIS; CONJUGATE ADDITION; OLEFIN METATHESIS; FORMAL SYNTHESIS;

D O I：

10.1002/ejoc.201500605

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A highly nucleophilic vinylation reagent, lithium vinyldimethylmagnesate (vinylMe(2)MgLi), is obtained by mixing vinylmagnesium chloride (1 equiv.) and MeLi (in diethoxymethane; 2 equiv.). The application of this new reagent in the completely regioselective synthesis of 6-vinyl-3,6-dihydro-1H-pyridin-2(1H)-ones by simple 1,6-additions to 2-pyridones is described. Examination of the scope and limitations of the addition revealed the influence on the efficiency of the 6-vinylation reaction of substituents on the nitrogen atom and on the 2-pyridone ring.

引用

页码：5189 / 5198

页数：10

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