Ethyl α-Nitrocinnamates in the Synthesis of Highly Functionalized Isoxazoles

被引：40

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

共 64 条

[21] [(3-Chlorophenyl)piperazinylpropyl]pyridazinones and analogues as potent antinociceptive agents [J].

Giovannoni, MP ;

Vergelli, C ;

Ghelardini, C ;

Galeotti, N ;

Bartolini, A ;

Dal Piaz, V .

JOURNAL OF MEDICINAL CHEMISTRY, 2003, 46 (06) :1055-1059

[22]

He Y., 1994, Synthesis, V9, P989

[23] Synthesis of 1,3-disubstituted naphthalenes from the Baylis-Hillman acetates with the aid of manganese(III) acetate [J].

Im, YJ ;

Lee, KY ;

Kim, TH ;

Kim, JN .

TETRAHEDRON LETTERS, 2002, 43 (26) :4675-4678

[24]

Jaeger V., 2002, Chem. Heterocyclic Compounds, V59, P361

[25] Manganese(III) acetate initiated oxidative free radical reactions between 2-amino-1,4-naphthoquinones and β-dicarbonyl compounds [J].

Jiang, MC ;

Chuang, CP .

JOURNAL OF ORGANIC CHEMISTRY, 2000, 65 (17) :5409-5412

[26] Synthesis and antibacterial activity of new carbapenems containing isoxazole moiety [J].

Kang, YK ;

Shin, KJ ;

Yoo, KH ;

Seo, KJ ;

Hong, CY ;

Lee, CS ;

Park, SY ;

Kim, DJ ;

Park, SW .

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2000, 10 (02) :95-99

[27] SYNTHESIS USING PYRIDINIUM SALTS .5. SPECIFIC SYNTHESIS OF PYRIDINES AND OLIGOPYRIDINES [J].

KROHNKE, F .

SYNTHESIS-STUTTGART, 1976, (01) :1-24

[28]

KROHNKE F, 1962, ANGEW CHEM INT EDIT, V74, P626

[29] SYNTHESIS OF DICATIONIC DIARYLPYRIDINES AS NUCLEIC-ACID BINDING-AGENTS [J].

KUMAR, A ;

RHODE, RA ;

SPYCHALA, J ;

WILSON, WD ;

BOYKIN, DW ;

TIDWELL, RR ;

DYKSTRA, CC ;

HALL, JE ;

JONES, SK ;

SCHINAZI, RF .

EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 1995, 30 (02) :99-106

[30] Synthesis and biological evaluation of N-heterocyclic indolyl glyoxylamides as orally active anticancer agents [J].

Li, WT ;

Hwang, DR ;

Chen, CP ;

Shen, CW ;

Huang, CL ;

Chen, TW ;

Lin, CH ;

Chang, YL ;

Chang, YY ;

Lo, YK ;

Tseng, HY ;

Lin, CC ;

Song, JS ;

Chen, HC ;

Chen, SJ ;

Wu, SH ;

Chen, CT .

JOURNAL OF MEDICINAL CHEMISTRY, 2003, 46 (09) :1706-1715

← 1 2 3 4 5 6 7 →