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通过非对映选择性自由基串联环化反应合成吲哚并二氮杂卓衍生物。

Diastereoselective radical cascade cyclization to access indole-fused diazepine derivatives.

作者信息

Wang Yutong, Huang Xiujuan, Chen Jinglong, Xu Jian, Song Qiuling

机构信息

College of Materials Science and Engineering, Fuzhou University, Fuzhou, Fujian 350108, China.

Institute of Next Generation Matter Transformation, College of Material Sciences Engineering at Huaqiao University, Xiamen, Fujian 361021, China.

出版信息

Org Biomol Chem. 2025 May 7;23(18):4349-4354. doi: 10.1039/d5ob00219b.

Abstract

The synthesis of polycyclic indoles is significant in organic chemistry, due to such heterocyclic frameworks being present in numerous bioactive pharmaceuticals and natural alkaloids. Herein, we provide an efficient radical cascade cyclization strategy to generate indole-fused diazepine derivatives using phosphoryl or sulfonyl radicals with -(2-(1-indol-1-yl)phenyl)--methylmethacrylamides. The merits of this synthesis are attributed to its accessible starting materials, broad substrate compatibility and excellent diastereoselectivity.

摘要

多环吲哚的合成在有机化学中具有重要意义,因为许多生物活性药物和天然生物碱中都存在这种杂环骨架。在此,我们提供了一种有效的自由基级联环化策略,使用磷酰基或磺酰基自由基与-(2-(1-吲哚-1-基)苯基)-甲基甲基丙烯酰胺生成吲哚稠合的二氮杂卓衍生物。这种合成方法的优点在于其起始原料易得、底物兼容性广以及出色的非对映选择性。

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