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

Frei, Przemysslaw and Jones, D. Heulyn and Kay, Steven T. and McLellan, Jayde A. and Johnston, Blair F. and Kennedy, Alan R. and Tomkinson, Nicholas C. O. (2018) Regioselective reaction of heterocyclic N-oxides, an acyl chloride and cyclic thioethers. Journal of Organic Chemistry. ISSN 0022-3263 (https://doi.org/10.1021/acs.joc.7b02457)

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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.

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