Transition‐Metal‐Free Radical Relay Cascade Annulation of Amides: Access to Antitumor Active Benzoazepine 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...

Full description

Saved in:
Bibliographic Details
Published in:Chemistry : a European journal 2024-11, Vol.30 (63)
Main Authors: Xia‐xin Sheng, Chao‐ying Qiu, Li‐na Wang, Yu‐jia Du, Lu‐ning Tang, Jia‐ming Chen, Guo‐ying Liu, Sen, Yang, Peng‐fei Zheng, Chen, Ming
Format: Article
Language:English
Subjects:
Amides
Antineoplastic drugs
Biological activity
Chemical activity
Chemical reactions
Free radicals
Hydrogen atoms
Irradiation
Light irradiation
Relay
Online Access:Get full text
Tags: Add Tag
No Tags, Be the first to tag this record!
Description
Summary: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.
ISSN:0947-6539
1521-3765
DOI:10.1002/chem.202402402