Photocatalytic Transition-Metal-Free Direct 3-Acetalation of Quinoxaline-2(1H)-ones
Photocatalytic Transition-Metal-Free Direct 3-Acetalation of Quinoxaline-2(1H)-ones
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DOI：
10.1002/cjoc.202200386
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发表时间：
2022-08-29
影响因子：
5.4
通讯作者：
Yu, Bing
中科院分区：
文献类型：
--
作者：
Ma, Chunhua;Meng, Hui;Yu, Bing
在温和的条件下，发展了一个不含过渡金属的可见光促进的喹喔啉-2（1H）-酮的3-缩醛化反应。通过使用1，2，3，5-四（咔唑-9-基）-4，6-二氰基苯（4CzIPN）作为廉价的光催化剂，乙醛酸缩醛作为自由基源，以中等至良好的产率构建了各种缩醛化的喹喔啉-2（1H）-酮。此外，该方案的多功能性突出了在药物分子的后期修饰和各种功能性转化中的成功应用。缩醛化产物的优异抗肿瘤活性表明，这种简化和可持续的方法可能成为药物化学结构修饰的有力策略。
Comprehensive Summary A general transition-metal-free visible-light-promoted 3-acetalation reaction of quinoxaline-2(1H)-ones was developed under mild conditions. By employing 1,2,3,5-tetrakis(carbazol-9-yl)-4,6-dicyanobenzene (4CzIPN) as an inexpensive photocatalyst, and glyoxylic acid acetal as a radical source, various acetalated quinoxaline-2(1H)-ones were constructed in moderate to good yields. Moreover, the versatility of this protocol is highlighted by the successful application in the late-stage modification of drug molecules and the various functionality transformations. The excellent antitumor activity of the acetalated product demonstrated that this streamlined and sustainable approach could have emerged as a powerful strategy for structural modification in medicinal chemistry.