Volume 2009, Issue 4 p. 564-574
Full Paper

Synthesis of (Alkylamino)nitroarenes by Oxidative Alkylamination of Nitroarenes

Anna V. Gulevskaya

Anna V. Gulevskaya

Department of Organic Chemistry, Southern Federal University, Zorge str. 7, Rostov-on-Don 344090, Russian Federation

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Stefan Verbeeck

Stefan Verbeeck

Department of Chemistry, University of Antwerp, Groenenborgerlaan 171, 2020 Antwerp, Belgium, Fax: +32-32653233

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Oleg N. Burov

Oleg N. Burov

Department of Organic Chemistry, Southern Federal University, Zorge str. 7, Rostov-on-Don 344090, Russian Federation

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Caroline Meyers

Caroline Meyers

Department of Chemistry, University of Antwerp, Groenenborgerlaan 171, 2020 Antwerp, Belgium, Fax: +32-32653233

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Inna N. Korbukova

Inna N. Korbukova

Department of Organic Chemistry, Southern Federal University, Zorge str. 7, Rostov-on-Don 344090, Russian Federation

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Wouter Herrebout

Wouter Herrebout

Department of Chemistry, University of Antwerp, Groenenborgerlaan 171, 2020 Antwerp, Belgium, Fax: +32-32653233

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Bert U. W. Maes

Bert U. W. Maes

Department of Chemistry, University of Antwerp, Groenenborgerlaan 171, 2020 Antwerp, Belgium, Fax: +32-32653233

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First published: 13 January 2009
Citations: 14

Dedicated to Professor Alexander F. Pozharskii on the occasion of his 70th birthday

Graphical Abstract

The viability of oxidative alkylamination for the derivatization of nitroarenes has been investigated. Nitroarenes are much more reactive than azines in this reaction.

Abstract

The viability of the oxidative alkylamination process for the derivatization of electron-deficient carboaromatics has been investigated. 1,3-Dinitrobenzene, 1-nitronaphthalene, and 1,5- and 1,8-dinitronaphthalenes have shown to react with a wide range of alkylamines in the presence of an oxidant (KMnO4, AgMnO4, AgPy2MnO4) to give access to the corresponding N-alkyl-nitroarenamines in moderate to good yields. Nitroarenes are more reactive than azines towards alkylamines.(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009)