BF3.OEt2-mediated C-C bond-forming reaction of α-hydroxyketene-(S,S)-acetals with active methylene compounds and its application in the synthesis of substituted 3,4-dihydro-2-pyridones

被引：14

作者：

Liu, Jun ^{[1
]}

Liang, Fushun ^{[1
]}

Liu, Qun ^{[1
]}

Li, Bing ^{[1
]}

机构：

[1] NE Normal Univ, Dept Chem, Changchun 130024, Peoples R China

来源：

SYNLETT | 2007年 / 01期

关键词：

C-C bond-forming reaction; alpha-hydroxyketene-(S; S)-acetals; active methylene compounds; substituted 3,4-dihydro-2-pyridones; one-pot synthesis;

D O I：

10.1055/s-2006-958412

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The C-C bond-forming reaction between alpha-hydroxy-ketene-(S,S)-acetals 2 and active methylene compounds is described. Mediated by boron trifluoride etherate (BF3 center dot OEt2), a series of C-C bond coupling products, 2-(2-acetyl-1-methyl-3-oxobutyl)-N-aryl-3,3-bis(ethylthio)acrylamides 3 was obtained in high to excellent yields by the reaction of 2a-e (R-1 = Ar) with acetylacetone. Various N-aryl-substituted 3,4-dihydropyridones 5 were prepared in high yields from 3 via a two-step procedure. Upon the reaction of 2f (R-1 = H) with active methylene compounds, 3,4-dihydropyridones 6 and/or 7, were obtained in a one-pot reaction with moderate to good yields.

引用

页码：156 / 160

页数：5

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