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

Jingyue Yang, Gregory B Dudley

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

The Journal of organic chemistry 2009 Oct 16

filter terms:

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.

Citation

Jingyue Yang, Gregory B Dudley. 1,2]-Anionic rearrangement of 2-benzyloxypyridine and related pyridyl ethers. The Journal of organic chemistry. 2009 Oct 16;74(20):7998-8000

PMID: 19761204

View Full Text