Synthesis of (Alkylamino)nitroarenes by Oxidative Alkylamination of Nitroarenes†
Anna V. Gulevskaya
Department of Organic Chemistry, Southern Federal University, Zorge str. 7, Rostov-on-Don 344090, Russian Federation
Search for more papers by this authorStefan Verbeeck
Department of Chemistry, University of Antwerp, Groenenborgerlaan 171, 2020 Antwerp, Belgium, Fax: +32-32653233
Search for more papers by this authorOleg N. Burov
Department of Organic Chemistry, Southern Federal University, Zorge str. 7, Rostov-on-Don 344090, Russian Federation
Search for more papers by this authorCaroline Meyers
Department of Chemistry, University of Antwerp, Groenenborgerlaan 171, 2020 Antwerp, Belgium, Fax: +32-32653233
Search for more papers by this authorInna N. Korbukova
Department of Organic Chemistry, Southern Federal University, Zorge str. 7, Rostov-on-Don 344090, Russian Federation
Search for more papers by this authorWouter Herrebout
Department of Chemistry, University of Antwerp, Groenenborgerlaan 171, 2020 Antwerp, Belgium, Fax: +32-32653233
Search for more papers by this authorBert U. W. Maes
Department of Chemistry, University of Antwerp, Groenenborgerlaan 171, 2020 Antwerp, Belgium, Fax: +32-32653233
Search for more papers by this authorAnna V. Gulevskaya
Department of Organic Chemistry, Southern Federal University, Zorge str. 7, Rostov-on-Don 344090, Russian Federation
Search for more papers by this authorStefan Verbeeck
Department of Chemistry, University of Antwerp, Groenenborgerlaan 171, 2020 Antwerp, Belgium, Fax: +32-32653233
Search for more papers by this authorOleg N. Burov
Department of Organic Chemistry, Southern Federal University, Zorge str. 7, Rostov-on-Don 344090, Russian Federation
Search for more papers by this authorCaroline Meyers
Department of Chemistry, University of Antwerp, Groenenborgerlaan 171, 2020 Antwerp, Belgium, Fax: +32-32653233
Search for more papers by this authorInna N. Korbukova
Department of Organic Chemistry, Southern Federal University, Zorge str. 7, Rostov-on-Don 344090, Russian Federation
Search for more papers by this authorWouter Herrebout
Department of Chemistry, University of Antwerp, Groenenborgerlaan 171, 2020 Antwerp, Belgium, Fax: +32-32653233
Search for more papers by this authorBert U. W. Maes
Department of Chemistry, University of Antwerp, Groenenborgerlaan 171, 2020 Antwerp, Belgium, Fax: +32-32653233
Search for more papers by this authorDedicated to Professor Alexander F. Pozharskii on the occasion of his 70th birthday
Graphical Abstract
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)
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