Regioselective Reaction of Heterocyclic N-Oxides, an Acyl Chloride, and Cyclic Thioethers,The Journal of Organic Chemistry

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Regioselective Reaction of Heterocyclic N-Oxides, an Acyl Chloride, and Cyclic Thioethers
The Journal of Organic Chemistry ( IF 3.3 ) Pub Date : 2018-01-18 00:00:00 , DOI: 10.1021/acs.joc.7b02457
Przemyslaw Frei ₁ , D. Heulyn Jones ₁ , Steven T. Kay ₁ , Jayde A. McLellan ₁ , Blair F. Johnston ₂ , Alan R. Kennedy ₁ , Nicholas C. O. Tomkinson ₁

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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.

中文翻译：

杂环氮氧化物，酰氯和环状硫醚的区域选择性反应

在三乙胺的存在下用4-硝基苯甲酰氯和环状硫醚处理缺电子的吡啶N-氧化物可得到相应的2-官能化产物，分离产率高达74％。所述转化也可以用替代的含氮杂环，包括喹啉，嘧啶和吡嗪来完成。为了扩大转化范围，可以使用二异丙醚作为反应介质，以允许使用固体硫醚底物。

更新日期：2018-01-18

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