ArticleJournal of the American Chemical Society2022
Unified Access to Pyrimidines and Quinazolines Enabled by N-N Cleaving Carbon Atom Insertion.
Article in Journal of the American Chemical Society, 2022. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 44 papers.
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Who cites it
44 citing papers in PubMed, 171 citations in OpenAlex.
- Violet-light-induced ring expansion of 2-aryl-1,3-indandiones with chlorodiazirines toward 1,4-naphthoquinones.Chemical science · 2026Article
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- Pyridine C─N Transposition via Cycloaddition-Cycloreversion.Angewandte Chemie (International ed. in English) · 2026Article
- Nitrogen atom insertion and related skeletal editing strategies in aromatic heterocycles for drug discovery (2015-2025).Molecular diversity · 2026Review
- Cyclic sulfone ring remodeling enables molecular shape diversity-oriented synthesis of privileged biaryl and oligoaryl motifs.Nature communications · 2026Article
- Strategic Applications of Single-Atom Skeletal Editing in Natural Product Synthesis.Journal of the American Chemical Society · 2026Review
- Bridged scaffold editing of carbocycles and heterocycles.Nature communications · 2026Article
- A difluorocarbene-triggered annulation/ring expansion cascadeChemical science · 2026Article
- Photoinduced polarity-mismatched transformations of isoquinolines into naphthalenes.Nature communications · 2026Article
- A Diazo-free Equivalent of the Unsubstituted Carbyne Cation: Straightforward Synthesis of Naphthalenes and Pyridines via [Journal of the American Chemical Society · 2026Article
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- Enantioselective dearomative single-atom skeletal editing of benzofurans.Nature communications · 2025Article
- Tunable Skeletal Editing of Benzothiazole and Benzisothiazole Via Carbene Transfer Reactions.JACS Au · 2025Article
- Synthesis ofJACS Au · 2025Article
- Skeletal editing of 4-arylpyrimidines into diverse nitrogen heteroaromatics via four-atom synthons.Nature communications · 2025Article
- The Versatility of Diazirines: Properties, Synthetic and Modern Applications.Chemistry (Weinheim an der Bergstrasse, Germany) · 2025Review
- Phototransposition of Indazoles to Benzimidazoles: Tautomer-Dependent Reactivity, Wavelength Dependence, and Continuous Flow Studies.Angewandte Chemie (International ed. in English) · 2025Article
- Precise control of selective nitrogen atom insertion into five-membered cyclic β-ketoesters.Nature communications · 2025Article
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Authors and funding
5 authors at 1 institution in 1 country.
Funding
Abstract
Given the ubiquity of heterocycles in biologically active molecules, transformations with the capacity to modify such molecular skeletons with modularity remain highly desirable. Ring expansions that enable interconversion of privileged heterocyclic motifs are especially interesting in this regard. As such, the known mechanisms for ring expansion and contraction determine the classes of heterocycle amenable to skeletal editing. Herein, we report a reaction that selectively cleaves the N-N bond of pyrazole and indazole cores to afford pyrimidines and quinazolines, respectively. This chlorodiazirine-mediated reaction provides a unified route to a related pair of heterocycles that are otherwise typically prepared by divergent approaches. Mechanistic experiments and DFT calculations support a pathway involving pyrazolium ylide fragmentation followed by cyclization of the ring-opened diazahexatriene intermediate to yield the new diazine core. Beyond enabling access to valuable heteroarenes from easily prepared starting materials, we demonstrate the synthetic utility of skeletal editing in the synthesis of a Rosuvastatin analog as well as in an aryl vector-adjusting direct scaffold hop.
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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.