[1,2]-Anionic rearrangement of 2-benzyloxypyridine and related pyridyl ethers
(Chemical Equation Presented) An anionic rearrangement of 2-benzyloxypyridine is described. Pyridine-directed metalation of the benzylic carbon leads to 1,2-migration of pyridine via a postulated associative mechanism (addition/elimination). Several aryl pyridyl carbinols were obtained in high yields. A formal synthesis of carbinoxamine, an antihistamine drug used for the treatment of seasonal allergies and hay fever, emerges from this methodology.
Yang, Jingyue,Dudley, Gregory B.
supporting information; experimental part
p. 7998 - 8000
(2010/03/01)
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