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Aldrich ChemFiles 2006, 6.6, 9.

Aldrich ChemFiles 2006, 6.6, 9.

Pyridines have been of interest to scientists across a number of disciplines. The pyridine moiety is presented in countless molecules with applications as varied as catalysis, drug design, molecular recognition, and natural product synthesis.

Recently, Blackaby and co-workers reacted a series of different pyridines with a common imidazo[1,2-a]pyrimidine core to create functionally selective GABAA ligands (Scheme 16).1 Another report described the use of 2-chloropyridines in the regioselective preparation of pyridin-2-yl ureas (Scheme 17).2

Scheme 16

Scheme 17

Schlosser has recently reported a method to reverse the selectivity of nucleophilic substitution on 2,4-substituted di-, tri-, and tetrahalopyridines by introducing a trialkylsilyl group in the 3- or 5-position. The bulky silyl group sterically blocks the 4-position, forcing substitution at the 2- or 6-position (Scheme 18).3

Scheme 18

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  1. Blackaby, W. P. et al. Bioorg. Med. Chem. Lett. 2006, 16, 1175.
  2. Abad, A. et al. Synthesis 2005, 915.
  3. (a) Schlosser, M. et al. J. Org. Chem. 2005, 70, 2494. (b) Schlosser, M. et al. Org. Lett. 2005, 7, 127.

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