Preparation of Heteroaryl Ethers from Azine N-Oxides and Alcohols

Org Lett. 2016 Mar 18;18(6):1362-5. doi: 10.1021/acs.orglett.6b00295. Epub 2016 Mar 9.

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.

MeSH terms

  • Alcohols / chemistry*
  • Azo Compounds / chemistry*
  • Catalysis
  • Ethers / chemical synthesis*
  • Ethers / chemistry
  • Molecular Structure
  • Oxides / chemistry*

Substances

  • Alcohols
  • Azo Compounds
  • Ethers
  • Oxides