Regioselective reaction of heterocyclic N-oxides, an acyl chloride and cyclic thioethers

Przemysslaw Frei, D. Heulyn Jones, Steven T. Kay, Jayde A. McLellan, Blair F. Johnston, Alan R. Kennedy, Nicholas C. O. Tomkinson

Research output: Contribution to journalArticlepeer-review

8 Citations (Scopus)
27 Downloads (Pure)

Abstract

Treatment of electron deficient pyridine N-oxides with 4-nitrobenzoyl chloride and a cyclic thioether in the presence of triethylamine leads to the corresponding 2-functionalized product in up to 74% iso-lated yield. The transformation can also be accomplished with alternative nitrogen containing hetero-cycles including quinolines, pyrimidines, and pyrazines. To expand the scope of the transformation diisopropyl ether can be used as the reaction medium to allow for the use of solid thioether substrates.
Original languageEnglish
Number of pages8
JournalJournal of Organic Chemistry
Early online date18 Jan 2018
DOIs
Publication statusE-pub ahead of print - 18 Jan 2018

Keywords

  • N-oxides
  • heterocycles
  • nitrogen

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