A. Schmidt, T. Mordhorst, M. Nieger
Dec 1, 2006
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Synthesis
Abstract
Pyridines, acting as heteroaromatic N-nucleophiles, 4-aminopyridine as an N,N-bisnucleophile, and 3,4-diaminopyridine as an N,N,N-trisnucleophile, all reacted with 4-(dimethylamino)-1-(2,3,5,6-tetrachloropyridin-4-yl)pyridinium chloride to give tris-pyridinio-substituted 3,5-dichloropyridines. Reaction of the same pyridinium chloride with O,O-bisnucleophiles such as 1,3-propanediol, hydroquinone, and resorcine, or the O,O,O-nucleophile phloroglucine, formed new Cl 2 ,Cl 3 ,O 4 ,Cl 5 ,Cl 6 and O 2 ,Cl 3 ,O 4 ,Cl 5 ,Cl 6 -substituted pyridines. S,O-Bisnucleophiles, such as 2-sulfanylethanol or 3-sulfanylpropionic acid gave the corresponding S-substituted pyridines (x-ray analysis). The (pyridin-4-yl)propionic acid was converted into bis(pyridinio)pyridine-4-thiol, an example of the rare class of N 2 ,Cl 3 ,S 4 ,Cl 5 ,N 6 -substituted pyridines.