title: Preparation of Heteroaryl Ethers from Azine N-Oxides and Alcohols.
abstract: The heteroaryl ether is an important structural feature in molecules of biological interest, yet it remains a challenge to synthesize. A new and practical method for the synthesis of heteroaryl ethers is reported. In the presence of PyBroP, a variety of nonaromatic alcohols readily add to azine N-oxides to afford the corresponding heteroaryl ethers. The reaction conditions are mild, economical, chemoselective, and compatible with a broad range of substrates. Thirty-eight examples are provided, as is a discussion of reaction optimization and mechanism.
authors.affiliation: Pfizer Worldwide Medicinal Chemistry , Eastern Point Road, Groton, Connecticut 06340, United States.
authors.forename: Yajing
authors.initials: Y
authors.lastname: Lian
authors.affiliation: Pfizer Worldwide Medicinal Chemistry , Eastern Point Road, Groton, Connecticut 06340, United States.
authors.forename: Steven B
authors.initials: SB
authors.lastname: Coffey
authors.affiliation: Pfizer Worldwide Medicinal Chemistry , Eastern Point Road, Groton, Connecticut 06340, United States.
authors.forename: Qifang
authors.initials: Q
authors.lastname: Li
authors.affiliation: Pfizer Worldwide Medicinal Chemistry , Eastern Point Road, Groton, Connecticut 06340, United States.
authors.forename: Allyn T
authors.initials: AT
authors.lastname: Londregan
mesh_terms: D000438:Alcohols / Q000737:chemistry*; D001391:Azo Compounds / Q000737:chemistry*; D002384:Catalysis; D004987:Ethers / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D010087:Oxides / Q000737:chemistry*
chemical_list: D000438:Alcohols; D001391:Azo Compounds; D004987:Ethers; D010087:Oxides