A new synthesis of oxcarbazepine using a Friedel-Crafts eyelization strategy

被引：24

作者：

Kaufmann, D ^{[1
]}

Fünfschilling, PC ^{[1
]}

Beutler, U ^{[1
]}

Hoehn, P ^{[1
]}

Lohse, O ^{[1
]}

Zaugg, W ^{[1
]}

机构：

[1] Novartis Pharma AG, Chem & Analyt Dev, CH-4002 Basel, Switzerland

来源：

TETRAHEDRON LETTERS | 2004年 / 45卷 / 27期

关键词：

Friedel-Crafts acylation; oxcarbazepine;

D O I：

10.1016/j.tetlet.2004.05.014

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A novel. simple, and straightforward process for the large-scale synthesis of oxcarbazepine, the active ingredient of Trileptal(R), a medicine for the treatment of epilepsy, has been developed. Starting from readily available l,3-dihydro-1-phenyl-2H-indol-2-one. a Friedel-Crafts cyclization strategy provides a direct route to the tricyclic framework of the target molecule. Crucial to the success of the strategy was the choice of the proper nitrogen-protecting group. (C) 2004 Elsevier Ltd. All rights reserved.

引用

页码：5275 / 5278

页数：4

共 12 条

[1]

AUFDERHAAR E, 1981, Patent No. 28028

[2] A kinetic study of the ammonolysis of phenylacetic esters in methanol solution [J].

Betts, RL ;

Hammett, LP .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1937, 59 :1568-1572

[3]

ENGEL J, 1998, EPILEPSY COMPREHENSI, V2

[4]

FUNFSCHILLING CP, UNPUB ORG PROCESS RE

[5] DIBENZ[B,F]AZEPINES AND RELATED RING-SYSTEMS [J].

KRICKA, LJ ;

LEDWITH, A .

CHEMICAL REVIEWS, 1974, 74 (01) :101-123

[6] New synthesis of oxcarbazepine via remote metalation of protected N-o-tolyl-anthranilamide derivatives [J].

Lohse, O ;

Beutler, U ;

Fünfschilling, P ;

Furet, P ;

France, J ;

Kaufmann, D ;

Penn, G ;

Zaugg, W .

TETRAHEDRON LETTERS, 2001, 42 (03) :385-389

[7]

Milanese A., 1996, WO Patent Application, Patent No. [9621649, 9,621,649]

[8] SYNTHESIS AND QUANTITATIVE STRUCTURE-ACTIVITY-RELATIONSHIPS OF DICLOFENAC ANALOGS [J].

MOSER, P ;

SALLMANN, A ;

WIESENBERG, I .

JOURNAL OF MEDICINAL CHEMISTRY, 1990, 33 (09) :2358-2368

[9] New practical synthesis of tenidap [J].

Porcs-Makkay, M ;

Simig, G .

ORGANIC PROCESS RESEARCH & DEVELOPMENT, 2000, 4 (01) :10-16

[10]

Schindler W., 1970, [No title captured], Patent No. [DE 2,011,087, CAN73:109711, 2011087]

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