Photoinduced radical cyclization reaction of isocyanides with α-carbonyl bromides to access 11-alkyl-substituted 1,4-dibenzodiazepines

Abstract

1,4-Dibenzodiazepines, an important component of nitrogen-containing heterocycles, are widely present in drugs. Herein, we developed a photochemical radical cascade cyclization reaction of isocyanides with α-carbonyl bromides under mild conditions. A sequence of 11-alkyl-substituted 1,4-dibenzodiazepines were produced in 53%–85% yields, demonstrating excellent tolerance towards various functional groups. Primary, secondary, and tertiary α-carbonyl bromides were effectively employed as alkyl reagents.

Graphical abstract: Photoinduced radical cyclization reaction of isocyanides with α-carbonyl bromides to access 11-alkyl-substituted 1,4-dibenzodiazepines

Supplementary files

Article information

Article type
Paper
Submitted
08 Dec 2024
Accepted
07 Jan 2025
First published
11 Jan 2025

Org. Biomol. Chem., 2025, Advance Article

Photoinduced radical cyclization reaction of isocyanides with α-carbonyl bromides to access 11-alkyl-substituted 1,4-dibenzodiazepines

A. Li, R. Xie, Q. Zhou, P. Huang and Y. Liu, Org. Biomol. Chem., 2025, Advance Article , DOI: 10.1039/D4OB01985G

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