Chemistry of halonitroethenes, 1:: First synthesis of functionalized 3-chloroquinoxalin-2(1H)-one 4-oxides

被引：16

作者：

Meyer, Christian ^{[1
]}

Zapol'skii, Viktor A. ^{[1
]}

Adam, Arnold E. W. ^{[2
]}

Kaufmann, Dieter E. ^{[1
]}

机构：

[1] Tech Univ Clausthal, Inst Organ Chem, D-38678 Clausthal Zellerfeld, Germany

[2] Tech Univ Clausthal, Inst Anorgan & Analyt Chem, D-38678 Clausthal Zellerfeld, Germany

来源：

SYNTHESIS-STUTTGART | 2008年 / 16卷 / 16期

关键词：

annulation; C-N coupling; amines; halides; nitro compounds; nitrones; quinoxalinones;

D O I：

10.1055/s-2008-1067207

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A one-pot annulation reaction of aniline and its ring-substituted derivatives with 1,1,2-trichloro-2-nitroethene (TCNiE) was developed delivering 3-chloroquinoxalin-2(1H)-one 4-oxides, exclusively, in good yields. The structure was proved by X-ray analysis. The C-N cyclization, a competing reaction to the double S(N)Vin reaction of 1,1,2-trichloro-2-nitroethene with amines, can be controlled by the mode of addition. Some of the resulting quinoxalinones are promising candidates with respect to their prospective biological, especially pharmacological, activity.

引用

页码：2575 / 2581

页数：7

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