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2005
Pyridine derivatives
R 0380
Tetrabutylammonium Salt Induced Denitration of Nitropyridines: Synthesis of
Hydroxy-, and Methoxypyridines. — The fluorodenitration of nitropyri27- 137 Fluoro-,
dines under the conditions shown is a mild and efficient alternative to the classical procedure for the synthesis of fluoropyridines. The reaction proceeds in good yields and
appears to be general for pyridines with nitro substitution at the 2- or 4-positions. 3-Nitropyridines require attendant electron-withdrawing groups for efficient conversion to
product. Hydroxy- and methoxydenitrations of substituted nitropyridines are carried
out with commercially available tetrabutylammonium salts to provide hydroxy- and
methoxypyridines in preparatively useful yields. — (KUDUK*, S. D.; DIPARDO, R.
M.; BOCK, M. G.; Org. Lett. 7 (2005) 4, 577-579; Dep. Med. Chem., Merck Res.
Lab., West Point, PA 19486, USA; Eng.) — Steudel
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