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

Frei, Przemyslaw, Jones, D. Heulyn, Kay, Steven T., McLellan, Jayde A., Johnston, Blair F., 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 83 (3) , pp. 1510-1517. 10.1021/acs.joc.7b02457

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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 a 74% isolated yield. The transformation can also be accomplished with alternative nitrogen containing heterocycles, 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.

Item Type: Article
Date Type: Publication
Status: Published
Schools: Biosciences
Publisher: American Chemical Society
ISSN: 0022-3263
Date of First Compliant Deposit: 18 May 2020
Date of Acceptance: 18 January 2018
Last Modified: 14 Nov 2023 14:40

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