We report the synthesis of a series of 2,6-disubstituted pyridines in a straightforward manner starting from readily available 2-substituted pyridines. The main sequence involves a selective ?́-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. © Wiley-VCH Verlag GmbH & Co. KGaA, 2008.
CITATION STYLE
Vandromme, L., Reißig, H. U., Gröper, S., & Rabe, J. P. (2008). Practical routes to 2,6-disubstituted pyridine derivatives. European Journal of Organic Chemistry, (12), 2049–2055. https://doi.org/10.1002/ejoc.200701200
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