Diastereoselective radical cascade cyclization to access indole-fused diazepine derivatives

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 <i>N</i>-(2-(1<i>H</i>-indol-1-yl)phenyl)-<i>N</i>-methylmethacrylamides. The merits of this synthesis are attributed to its accessible starting materials, broad substrate compatibility and excellent diastereoselectivity.

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Publication Details

Journal
Organic & Biomolecular Chemistry
Published
2025-01-01
DOI
https://doi.org/10.1039/d5ob00219b
Primary Topic
Radical Photochemical Reactions
Type
article
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article

Diastereoselective radical cascade cyclization to access indole-fused diazepine derivatives

Jian Xu, Qiuling Song, Xiujuan Huang, Yutong Wang et al.
3 links
Organic & Biomolecular Chemistry
Radical Photochemical Reactions
article

Diastereoselective radical cascade cyclization to access indole-fused diazepine derivatives

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

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 <i>N</i>-(2-(1<i>H</i>-indol-1-yl)phenyl)-<i>N</i>-methylmethacrylamides. The merits of this synthesis are attributed to its accessible starting materials, broad substrate compatibility and excellent diastereoselectivity.

Organic & Biomolecular ChemistryVol. 23(18)
Huaqiao University (CN), Fuzhou University (CN), Fujian University of Technology (CN), Nanjing University (CN)
Openalex Percentile: Top 95%
Radical Photochemical Reactions
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Diastereoselective radical cascade cyclization to access indole-fused diazepine derivatives — Jian Xu, Qiuling Song, et al. · Organic & Biomolecular Chemistry (2025) | TGRS Research Map | TGRS