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

[1] Conjugate additions of nitroalkanes to electron-poor alkenes: Recent results [J].

Ballini, R ;

Bosica, G ;

Fiorini, D ;

Palmieri, A ;

Petrini, M .

CHEMICAL REVIEWS, 2005, 105 (03) :933-971

[2] ON THE OXIMATION OF DIARYL-BETA-DIKETONES [J].

BANDIERA, T ;

GRUNANGER, P ;

ALBINI, FM .

JOURNAL OF HETEROCYCLIC CHEMISTRY, 1992, 29 (06) :1423-1428

[3] USEFUL, REGIOSPECIFIC SYNTHESIS OF ISOXAZOLES [J].

BARBER, GN ;

OLOFSON, RA .

JOURNAL OF ORGANIC CHEMISTRY, 1978, 43 (15) :3015-3021

[4] Synthesis of cucurbitine derivatives: facile straightforward approach to methyl 3-amino-4-aryl-1-methylpyrrolydine-3-carboxylates [J].

Blanco-Ania, Daniel ;

Hermkens, Pedro H. H. ;

Sliedregt, Leo A. J. M. ;

Scheeren, Hans W. ;

Rutjes, Floris P. J. T. .

TETRAHEDRON, 2009, 65 (27) :5393-5401

[5] A novel microwave-mediated one-pot synthesis of indolizines via a three-component reaction [J].

Bora, U ;

Saikia, A ;

Boruah, RC .

ORGANIC LETTERS, 2003, 5 (04) :435-438

[6]

BUDAGYANTS MI, 1969, ZH ORG KHIM, V5, P1803

[7] Stereoselective synthesis of highly substituted trans-2,3-dihydrofuran and trans-1,2-cyclopropane derivatives containing sulfonyl groups [J].

Cao, Weiguo ;

Zhang, Hui ;

Chen, Jie ;

Zhou, Xiaohong ;

Shao, Min ;

McMills, Mark C. .

TETRAHEDRON, 2008, 64 (01) :163-167

[8] 1,2,5-oxadiazole (Furazan) derivatives from benzoylnitromethane and dipolarophiles in the presence of DABCO: Structure and intermediates [J].

Cecchi, Luca ;

De Sarlo, Francesco ;

Faggi, Cristina ;

Machetti, Fabrizio .

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2006, 2006 (13) :3016-3020

[9] Highly diastereoselective condensation of α-nitro-esters with aldehydes catalyzed by zinc complexes of amino acids [J].

Chatterjee, A ;

Jha, SC ;

Joshi, NN .

TETRAHEDRON LETTERS, 2002, 43 (30) :5287-5289

[10] Free radical reaction between 2-benzoyl-1,4-benzoquinones and 1,3-dicarbonyl compounds [J].

Chen, Kuang-Po ;

Lee, Hen-Qun ;

Cheng, Yu-Chih ;

Chuang, Che-Ping .

ORGANIC & BIOMOLECULAR CHEMISTRY, 2009, 7 (19) :4074-4081

← 1 2 3 4 5 6 7 →