Synthesis of Polyhalogenated
2-(Phenylamino)pyridines by Thermal Amination Reactions

Siegfried R. Waldvogel; Andreas Faust; Werner Barkmann; Roland Fröhlich; Oliver Wolff

doi:10.1055/s-0029-1216642

PAPER

Synthesis of Polyhalogenated 2-(Phenylamino)pyridines by Thermal Amination Reactions

Siegfried R. Waldvogel*^a, Andreas Faust^b, Werner Barkmann^c, Roland Fröhlich^c, Oliver Wolff^a
^a Kekulé-Institut für Organische Chemie und Biochemie, Rheinische Friedrich-Wilhelms-Universität Bonn, Gerhard-Domagk-Str. 1, 53121 Bonn, Germany
Fax: +49(228)739608; e-Mail: waldvogel@uni-bonn.de;
^b Klinik und Poliklinik für Nuklearmedizin, Universitätsklinikum Münster, Domagkstr. 5, 48149 Münster, Germany
^c Organisch-Chemisches Institut, Westfälische Wilhelms-Universität Münster, Corrrensstr. 40, 48149 Münster, Germany

Abstract

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Abstract

Amination reactions of 2,6-dibromopyridine with a variety of halogenated anilines were achieved thermally when 2,2,6,6-tetramethylpiperidine was employed as an auxiliary base. The solvent-free thermal conversion was superior to palladium-catalyzed transformations of such substrates since no high-molecular-weight byproducts were observed.

Key words

aminations - nucleophilic aromatic substitutions - pyridines - tetramethylpiperidine - anilines - polyhalogenated

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