Key Laboratory of Bioorganic Phosphorus Chemistry and Chemical Biology (Ministry of Education), Department of Chemistry, Tsinghua University , Beijing 100084, China.
J Am Chem Soc. 2017 Oct 11;139(40):14237-14243. doi: 10.1021/jacs.7b07883. Epub 2017 Oct 3.
Quinolones and isoquinolones exhibit diverse biological and pharmaceutical activities, and their synthesis is highly desirable under mild conditions. Here, a highly efficient and environmentally friendly visible light-mediated aerobic oxidation of readily available N-alkylpyridinium salts has been developed with Eosin Y as the organic photocatalyst and air as the terminal oxidant, and the reaction provided quinolones and isoquinolones in good yields. The method shows numerous advantages including mild and environmentally friendly conditions, high efficiency, tolerance of wide functional groups and low cost. Furthermore, 4-desoxylonimide with important pharmaceutical activities was effectively prepared by using our method. Therefore, the present method should provide a novel and useful strategy for synthesis and modification of N-heterocycles.
喹诺酮类和异喹啉酮类具有多样的生物和药物活性，并且在温和条件下对它们的合成具有很高的需求。在这里，我们开发了一种高效且环保的可见光介导的有氧氧化反应，使用曙红 Y 作为有机光催化剂，以空气作为末端氧化剂，可从易得的 N-烷基吡啶鎓盐出发，以良好的收率得到喹诺酮类和异喹啉酮类化合物。该方法具有许多优点，包括温和的反应条件、高效、对广泛的官能团的容忍性以及低成本。此外，我们的方法还可有效地制备具有重要药物活性的 4-脱羟洛尼定。因此，本方法应为 N-杂环的合成和修饰提供一种新颖而有用的策略。
