ArticleNature chemistry2025
Switchable skeletal editing of quinolines enabled by cyclizative sequential rearrangements.
Article in Nature chemistry, 2025. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 11 papers.
What it found
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The trial behind it
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Who cites it
11 citing papers in PubMed.
- C3-H methylenephosphonylation of azaarenes enabled by catalyst-controlled regioselective cyclizative rearrangement.Chemical science · 2026Article
- Article
- Decoding skeletal diversity and complexity: A biomimetic and photochemical remodeling strategy.Science advances · 2026Article
- Mechanochemical Single-Carbon Insertion into (Iso)quinolines.Nature communications · 2026Article
- Photochemical skeletal editing: one-step transformation of diaryl dithiophenes into regiodefined helicenes.Chemical science · 2026Article
- Regiodivergent C3 and C4 Amination of Quinolines via Radical and Ionic Pathways.Angewandte Chemie (International ed. in English) · 2026Article
- E/Z Isomerization-Enabled Conversion from Dual-Carbon to Single-Carbon Insertion into an Aromatic System.JACS Au · 2026Article
- Article
- Skeletal editing of 4-arylpyrimidines into diverse nitrogen heteroaromatics via four-atom synthons.Nature communications · 2025Article
- Rh-Catalyzed Atroposelective Single-Carbon Insertion.Journal of the American Chemical Society · 2025Article
- Carbon-Atom Scavengers Enable Divergent, Selective Carbon Deletion of Azaarenes.Journal of the American Chemical Society · 2025Article
Corrections and comments
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Authors and funding
5 authors.
Funding
Abstract
The rapid diversification of core ring structures in complex molecules through switchable skeletal editing is valuable in the drug discovery process. However, controllable methods for chemically divergent modifications of azaarene frameworks using common substrates are challenging, despite the potential to maximize structural diversity and complexity. Here we report the tunable skeletal editing of quinolines through Brønsted acid-catalysed multicomponent reactions of quinoline N-oxides, dialkyl acetylenedicarboxylates and water to generate nitrogen-containing heteroaromatic compounds together with linear compounds in a modular fashion. Specifically, in a one-pot procedure, after cyclization and sequential rearrangement processes, the quinoline N-oxides are easily converted into unique 2-substituted indolines. These then undergo acid-promoted fragmentation to give indoles, base-facilitated ring-opening to afford 2-alkenylanilines and oxidative cyclization to yield isoquinolinones. Catalytic asymmetric skeletal editing of quinolines is also realized, providing enantioenriched benzazepines bearing quaternary stereocentres, and late-stage skeletal modification of quinoline cores in several drugs is demonstrated.
Identifiers
40195435What OpenQuestion holds
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.