Transition‐Metal‐Free Radical Relay Cascade Annulation of Amides: Access to Antitumor Active Benzo[b]azepine and Oxindole Derivatives

Efficient transition-metal-free synthesis of benzo[b]azepines and oxindoles is achieved via a radical relay cascade strategy employing halogen atom transfer (XAT) for aryl radical generation followed by intramolecular hydrogen atom transfer (HAT). Optimization yielded moderate to substantial yields under visible light irradiation. Preliminary biological assessments revealed promising anti-tumor activity for select compounds. This study underscores the potential of XAT-mediated radical relay cascades in medicinal chemistry and anticancer drug discovery.

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Publication Details

Journal
Chemistry - A European Journal
Published
2024-08-26
DOI
https://doi.org/10.1002/chem.202402402
Citations
4
Primary Topic
Radical Photochemical Reactions
Type
article
Field-Weighted Citation Impact
1.00

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article

Transition‐Metal‐Free Radical Relay Cascade Annulation of Amides: Access to Antitumor Active Benzo[b]azepine and Oxindole Derivatives

Luning Tang, Yu-jia Du, Xia-xin Sheng, Lina Wang et al.
4 citations
Chemistry - A European Journal
Radical Photochemical Reactions
1.00
article

Transition‐Metal‐Free Radical Relay Cascade Annulation of Amides: Access to Antitumor Active Benzo[b]azepine and Oxindole Derivatives

Luning Tang, Yu-jia Du, Xia-xin Sheng, Lina Wang, Ming Chen, Jiaming Chen, Sen Yang, Chao-ying Qiu, Guoying Liu
article en
4 citations

Abstract

Efficient transition-metal-free synthesis of benzo[b]azepines and oxindoles is achieved via a radical relay cascade strategy employing halogen atom transfer (XAT) for aryl radical generation followed by intramolecular hydrogen atom transfer (HAT). Optimization yielded moderate to substantial yields under visible light irradiation. Preliminary biological assessments revealed promising anti-tumor activity for select compounds. This study underscores the potential of XAT-mediated radical relay cascades in medicinal chemistry and anticancer drug discovery.

Chemistry - A European JournalVol. 30(63)
Army Medical University (CN), Changzhou University (CN)
National Outstanding Youth Science Fund Project of National Natural Science Foundation of China
Good health and well-being
Openalex Percentile: Top 27%
Radical Photochemical Reactions
1.00
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