Tetrabutylammonium salt induced denitration of nitropyridines: synthesis of fluoro-, hydroxy-, and methoxypyridines |
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Authors: | Kuduk Scott D DiPardo Robert M Bock Mark G |
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Institution: | Department of Medicinal Chemistry, Merck Research Laboratories, West Point, PA 19486, USA. scott_d_kuduk@merck.com |
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Abstract: | An efficient method for the synthesis of fluoropyridines via the fluorodenitration reaction is reported. The reaction is mediated by tetrabutylammonium fluoride (TBAF) under mild conditions without undue regard to the presence of water. The fluorodenitration is general for 2- or 4-nitro-substituted pyridines, while 3-nitropyridines require attendant electron-withdrawing groups for the reaction to proceed efficiently. Nitropyridines also undergo hydroxy- and methoxydenitration under mild conditions in the presence of the corresponding tetrabutylammonium species. reaction: see text] |
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