Practical Routes to 2,6-Disubstituted Pyridine Derivatives.

L. Vandromme, H.-U. Reissig, S. Gröper, J. P. Rabe – 2008

We report the synthesis of a series of 2,6-disubstitutedpyridines in a straightforward manner starting from readily available 2-substituted pyridines. The main sequence involves a selective α-lithiation reaction with halogen functionalization followed by a Grignard reaction catalyzed by Fe(acac)3. After demonstration of the easy feasibility of this strategy by synthesizing 2,6-disubstituted pyridines 1, the route was applied to obtain pyridine derivatives bearing electron-donating or electron-withdrawing groups. Thus, a series of pyridines bearing an aryl moiety in the 6-position and an alkyl chain in the 2-position was obtained. The pyridines were studied for their self-assembly abilities at the interface between an organic solution and the basal plane of graphite. Preliminary STM results for one compound are reported.

Titel
Practical Routes to 2,6-Disubstituted Pyridine Derivatives.
Verfasser
L. Vandromme, H.-U. Reissig, S. Gröper, J. P. Rabe
Datum
2008
Kennung
10.1002/ejoc.200701200
Quelle/n
Zitierweise
Eur. J. Org. Chem. 2008, 12, 2049.
Art
Text
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