Selective reduction of the nitro group in the presence of the azoxy group.: Synthesis of 2-(alkyl-NNO-azoxy)anilines

被引：6

作者：

Lipilin, DL ^{[1
]}

Churakov, AM ^{[1
]}

Strelenko, YA ^{[1
]}

Tartakovsky, VA ^{[1
]}

机构：

[1] Russian Acad Sci, ND Zelinskii Organ Chem Inst, Moscow 119991, Russia

来源：

RUSSIAN CHEMICAL BULLETIN | 2002年 / 51卷 / 02期

关键词：

nitrosobenzenes; nitrobenzenes; anilines; azoxy compounds; reduction of the nitro group;

D O I：

10.1023/A:1015463912286

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Tin(II) chloride selectively reduces the aromatic nitro group to the amino group, the azoxy group remaining intact. This allows the preparation of 2-(R-NNO-azoxy)anilines from 2-(R-NNO-azoxy)nitrobenzenes bearing electron-donating or weak electron-withdrawing substituents (Me or Br) in the benzene ring and alkyl substituents at the distal N atom of the azoxy group. The presence of electron-withdrawing substituents at the azoxy group (for example, CO2Et) leads to a change in the direction of the reaction resulting in selective reduction of the azoxy group to the hydrazo group.

引用

页码：311 / 318

页数：8

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