Interesting results of catalytic hydrogenation of 3-(2-nitrophenyl)isoxazoles and 3-(nitrophenyl)-4,5-dihydroisoxazoles

被引：16

作者：

Singh, V.

Madapa, S.

Yadav, G. P.

Maulik, P. R.

Batra, S.

机构：

[1] Cent Drug Res Inst, Div Med Chem, Lucknow 226001, Uttar Pradesh, India

[2] Cent Drug Res Inst, Mol & Struct Biol Div, Lucknow 226001, Uttar Pradesh, India

来源：

SYNTHESIS-STUTTGART | 2006年 / 12期

关键词：

isoxazole; 4-aminoquinoline; hydrogenation; ring transformation; regiospecific;

D O I：

10.1055/s-2006-942388

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The palladium-on-carbon assisted hydrogenolysis of substituted 3-(2-nitrophenyl)isoxazoles, irrespective of substitution on the isoxazole ring, invariably leads to reduction of the nitro to the amino group with concomitant regiospecific ring closure to yield substituted 4-aminoquinolines. In contrast similar hydrogenation of 3-(2-, 3-, and 4-nitrophenyl)-4,5-dihydroisoxazoles (2-isoxazolines) results in reduction of the nitro group only with conservation of the dihydroisoxazole ring to yield the corresponding 3-(aminophenyl)-4,5-dihydroisoxazoles.

引用

收藏

页码：1995 / 2004

页数：10

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