ArticleChemical science2024
Nitrogen atom insertion into arenols to access benzazepines.
Article in Chemical science, 2024. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 9 papers.
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Who cites it
9 citing papers in PubMed.
- Embracing triplet nitrenes for C-to-N replacement of complex bicyclic (hetero)aryl azides.Science (New York, N.Y.) · 2026Article
- Nitrogen atom insertion and related skeletal editing strategies in aromatic heterocycles for drug discovery (2015-2025).Molecular diversity · 2026Review
- Shape-Conserving Atom Replacements.Chemical reviews · 2026Review
- Formal pyridine meta-azidation and its application for the synthesis of diazepines, ring-fused δ-carbolines and 1,2,3-triazolylpyridines.Nature communications · 2025Article
- Precise control of selective nitrogen atom insertion into five-membered cyclic β-ketoesters.Nature communications · 2025Article
- Carbon-Atom Scavengers Enable Divergent, Selective Carbon Deletion of Azaarenes.Journal of the American Chemical Society · 2025Article
- Synthesis of naphthalene derivatives via nitrogen-to-carbon transmutation of isoquinolines.Science advances · 2025Article
- Carbon-nitrogen transmutation in polycyclic arenol skeletons to access N-heteroarenes.Nature communications · 2024Article
- Skeletal Editing: Ring Insertion for Direct Access to Heterocycles.Molecules (Basel, Switzerland) · 2024Review
Corrections and comments
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Authors and funding
5 authors.
Funding
No grant is acknowledged in the PubMed record.
Abstract
Advances in site-selective molecular editing have enabled structural modification on complex molecules. However, thus far, their applications have been restricted to C-H functionalization chemistry. The modification of the underlying molecular skeleton remains limited. Here, we describe a skeletal editing approach that provides access to benzazepine structures through direct nitrogen atom insertion into arenols. Using widely available arenols as benzazepine precursors, this alternative approach allowed the streamlined assembly of benzazepines with broad functional group tolerance. Experimental mechanistic studies support a reaction pathway involving dearomatizative azidation and then aryl migration. This study further highlights the potential for carbon-nitrogen transmutation sequences through combinations with oxidative carbon atom deletion, providing an alternative for the development of N-heteroarenes and demonstrating significant potential in materials chemistry.
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Registered trials
Read under generation 80e0d062 · epoch 390. Bibliography from PubMed, PubMed Central and OpenAlex; grants from NIH RePORTER; trial links from ClinicalTrials.gov; estimates, votes and beliefs from the OpenQuestion graph.