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[1,2]-Anionic rearrangement of 2-benzyloxypyridine and related pyridyl ethers.

Abstract
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.
AuthorsJingyue Yang, Gregory B Dudley
JournalThe Journal of organic chemistry (J Org Chem) Vol. 74 Issue 20 Pg. 7998-8000 (Oct 16 2009) ISSN: 1520-6904 [Electronic] United States
PMID19761204 (Publication Type: Journal Article)

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