The reaction of nitrones with pyrroles and furan:: an easy access to heteroaromatic hydroxylamines and bis(heteroaryl)alkanes

被引：13

作者：

Berini, C ^{[1
]}

Minassian, F ^{[1
]}

Pelloux-Léon, N ^{[1
]}

Vallée, Y ^{[1
]}

机构：

[1] Univ Grenoble 1, Etud Dynam & Struct Select Lab, UMR 5616,FR 2607, CNRS,Inst Chim Mol Grenoble, F-38041 Grenoble, France

来源：

TETRAHEDRON LETTERS | 2005年 / 46卷 / 50期

关键词：

nitrones; pyrroles; furan; hydroxylamines; 2,2'-bis(heteroaryl)alkanes;

D O I：

10.1016/j.tetlet.2005.10.061

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

N-Benzylnitrones react with heteroaromatic compounds such as pyrroles or furan in the presence of hydrogen chloride. Either heteroaromatic N-benzylhydroxylamines, symmetrical or unsymmetrical 2,2'-bis(heteroaryl)alkanes could be selectively produced depending on the experimental conditions. (c) 2005 Elsevier Ltd. All rights reserved.

引用

页码：8653 / 8656

页数：4

共 27 条

[1] A new approach to the synthesis of long-chain polypropionates based on the Diels-Alder monoadditions of 2,2'-ethylidenebis[3,5-dimethylfuran] [J].

Ancerewicz, J ;

Vogel, P .

HELVETICA CHIMICA ACTA, 1996, 79 (05) :1393-1414

[2] THE REACTION OF THIOIMIDES WITH PHOSPHORUS YLIDES [J].

BISHOP, JE ;

OCONNELL, JF ;

RAPOPORT, H .

JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (17) :5079-5091

[3] INSECTICIDAL ACTION OF HETEROCYCLIC ANALOGS OF 2,2,2-TRICHLORO-1-(PARA-CHLOROPHENYL)-ETHANOL [J].

BLINN, RC ;

GUNTHER, FA ;

METCALF, RL .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1954, 76 (01) :37-39

[4] First isolation of both indolylcarbinols and diindolylalkanes from microwave-assisted acid (clay)-catalysed reaction of indoles with diethyl ketomalonate [J].

Chakrabarty, M ;

Karmakar, S ;

Harigaya, Y .

HETEROCYCLES, 2005, 65 (01) :37-48

[5] The reactions of nitrones with indoles [J].

Chalaye-Mauger, H ;

Denis, JN ;

Averbuch-Pouchot, MT ;

Vallée, Y .

TETRAHEDRON, 2000, 56 (05) :791-804

[6]

Cho WS, 1998, B KOR CHEM SOC, V19, P314

[7]

Clayden J., 2001, ORGANIC CHEM, P1157

[8] SYNTHESIS OF N-BENZYL NITRONES [J].

DONDONI, A ;

FRANCO, S ;

JUNQUERA, F ;

MERCHAN, F ;

MERINO, P ;

TEJERO, T .

SYNTHETIC COMMUNICATIONS, 1994, 24 (18) :2537-2550

[9] Stereoselective addition of 2-furyllithium and 2-thiazolyllithium to sugar nitrones. Synthesis of carbon-linked glycoglycines [J].

Dondoni, A ;

Junquera, F ;

Merchan, FL ;

Merino, P ;

Scherrmann, MC ;

Tejero, T .

JOURNAL OF ORGANIC CHEMISTRY, 1997, 62 (16) :5484-5496

[10] Acyclic oxyiminium ions. Mannich reactions and addition of Grignard reagents [J].

Grigg, R ;

Rankovic, Z ;

Thoroughgood, M .

TETRAHEDRON, 2000, 56 (40) :8025-8032

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