Synthesis 2012; 44(18): 2959-2963
DOI: 10.1055/s-0032-1316749
paper
© Georg Thieme Verlag Stuttgart · New York

Synthesis of Azabipyridine and Azaterpyridine Building Blocks for Multitopic Binding

Soumen De
Center of Micro and Nanochemistry and Engineering, Organische Chemie I, Universität Siegen, Adolf-Reichwein-Str. 2, 57068 Siegen, Germany, eMail: schmittel@chemie.uni-siegen.de
,
Susnata Pramanik
Center of Micro and Nanochemistry and Engineering, Organische Chemie I, Universität Siegen, Adolf-Reichwein-Str. 2, 57068 Siegen, Germany, eMail: schmittel@chemie.uni-siegen.de
,
Michael Schmittel*
Center of Micro and Nanochemistry and Engineering, Organische Chemie I, Universität Siegen, Adolf-Reichwein-Str. 2, 57068 Siegen, Germany, eMail: schmittel@chemie.uni-siegen.de
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Publikationsverlauf

Received: 14. Mai 2012

Accepted after revision: 23. Juni 2012

Publikationsdatum:
03. August 2012 (online)


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Abstract

We describe the synthesis of four bromo-substituted azabipyridines­ and two bromo-substituted azaterpyridines through a series of palladium-catalyzed cross-coupling reactions. Both the azabipyridine and azaterpyridine heterocycles contain two orthogonal binding motifs, the value of which has been demonstrated recently in a nanomechanical switch for triggering organocatalysis. The bromo functionality allows heterocyclic ligands to be attached to larger frameworks.

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