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J Org Chem. 2009 Oct 16;74(20):7998-8000. doi: 10.1021/jo901707x.

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

Author information

1
Department of Chemistry and Biochemistry, Florida State University, Tallahassee, Florida 32306-4390, USA.

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.

PMID:
19761204
DOI:
10.1021/jo901707x

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