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Synthesis 2009(10): 1651-1654  
DOI: 10.1055/s-0029-1216642
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

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

Siegfried R. Waldvogel*a, Andreas Faustb, Werner Barkmannc, Roland Fröhlichc, Oliver Wolffa
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
Further Information

Publication History

Received 3 January 2009
Publication Date:
14 April 2009 (online)

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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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