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.
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Authors | Jingyue Yang, Gregory B Dudley |
Journal | The Journal of organic chemistry
(J Org Chem)
Vol. 74
Issue 20
Pg. 7998-8000
(Oct 16 2009)
ISSN: 1520-6904 [Electronic] United States |
PMID | 19761204
(Publication Type: Journal Article)
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