Selective reduction of the nitro group in the presence of the azoxy group. Synthesis of 2-(alkyl-NNO-azoxy)anilines |
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Authors: | Lipilin D L Churakov A M Strelenko Yu A Tartakovsky V A |
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Institution: | (1) Russian Academy of Sciences, N. D. Zelinsky Institute of Organic Chemistry, 47 Leninsky prosp., 119991 Moscow, Russian Federation |
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Abstract: | 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. |
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Keywords: | nitrosobenzenes nitrobenzenes anilines azoxy compounds reduction of the nitro group |
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