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

页码：5292 / 5300

页数：9

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