Ethyl α-Nitrocinnamates in the Synthesis of Highly Functionalized Isoxazoles

被引：39
|
作者：
Chen, Kuang-Po [1 ]
Chen, Yu-Jyun [1 ]
Chuang, Che-Ping [1 ]
机构：
[1] Natl Cheng Kung Univ, Dept Chem, Tainan 70101, Taiwan
来源：
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2010年 / 2010卷 / 27期
关键词：
Nitrogen heterocycles; Michael addition; Alkylation; Multicomponent reactions; FREE-RADICAL REACTIONS; 1,3-DIPOLAR CYCLOADDITION REACTIONS; ADDITION-RING-CLOSURE; ONE-POT SYNTHESIS; REGIOSPECIFIC SYNTHESIS; PYRIDINIUM YLIDES; N-(CYANOMETHYL)PYRIDINIUM YLIDES; STEREOSELECTIVE-SYNTHESIS; CYCLIZATION REACTIONS; EFFICIENT SYNTHESIS;
D O I：
10.1002/ejoc.201000401
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
An effective method for the synthesis of highly functionalized isoxazoles from readily available starting ethyl u-nitrocinnamates has been developed. Ethyl u-nitrocinnamates react smoothly with alpha-nitro carbonyl compounds to produce isoxazoles in good yields. Michael addition of pyridinium ylides to ethyl alpha-nitrocinnamates can also produce these isoxazoles effectively. These pyridinium salts can be generated in situ from the corresponding alkyl bromides. The one-pot multicomponent process was also developed. Isoxazoles can be produced directly from readily available aromatic aldehydes, ethyl nitroacetate, and pyridinium salts.
引用
收藏
页码：5292 / 5300
页数：9
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