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

Article Details

Citation

Copy to clipboard

Yang J, Dudley GB

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

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

PubMed ID

19761204 [ View in PubMed

]

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.

DrugBank Data that Cites this Article

Drug Targets

Drug	Target	Kind	Organism	Pharmacological Action	Actions
Carbinoxamine	Histamine H1 receptor	Protein	Humans	Yes	Antagonist	Details