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

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.

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Publication Details

Journal
Organic & Biomolecular Chemistry
Published
2025-01-01
DOI
https://doi.org/10.1039/d4ob01985g
Citations
3
Primary Topic
Radical Photochemical Reactions
Type
article
Field-Weighted Citation Impact
2.81

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article

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

R.-Q. Xie, Peng‐Fei Huang, Ao-Long Li, Quan Zhou et al.
3 citations
Organic & Biomolecular Chemistry
Radical Photochemical Reactions
2.81
article

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

R.-Q. Xie, Peng‐Fei Huang, Ao-Long Li, Quan Zhou, Yu Liu
article en
3 citations

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.

Organic & Biomolecular ChemistryVol. 23(8)
Hunan Institute of Science and Technology (CN)
Education Department of Hunan Province, National Natural Science Foundation of China, Natural Science Foundation of Hunan Province
Clean water and sanitation
Openalex Percentile: Top 12%
Radical Photochemical Reactions
2.81
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