One-Pot Deprotonative Synthesis of Biarylazacyclooctynones
One-Pot Deprotonative Synthesis of Biarylazacyclooctynones
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DOI：
10.1055/s-0039-1691491
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发表时间：
2020-01-24
期刊：
影响因子：
2
通讯作者：
Okano, Kentaro
中科院分区：
文献类型：
--
作者：
Hioki, Yuto;Itoh, Mayu;Okano, Kentaro
描述了从相应的烯醇三氟甲磺酸酯去质子化形成二芳基氮杂环辛酮（BARAC）。该反应在 -78 摄氏度下在一小时内提供氮杂环辛炔酮。该过程可以在一锅中从起始酮进行，以中等至优异的产率提供一系列 BARAC 衍生物。该方案通过减少反应步骤数量，实现了克级 BARAC 骨架的形成。此外，所建立的方法还应用于合成带有香豆素部分的BARAC衍生物。
Deprotonative formation of biarylazacyclooctynone (BARAC) from the corresponding enol triflate is described. The reaction furnished the azacyclooctynone within one hour at -78 degrees C. This process could be performed in one pot from the starting ketone to provide a range of BARAC derivatives in moderate to excellent yields. The protocol enabled the gram-scale formation of the BARAC skeleton by reducing the number of reaction steps. Furthermore, the established method was applied to the synthesis of the BARAC derivative bearing a coumarin moiety.