ArticleOrganic letters2017
Mechanistic Pathways in Amide Activation: Flexible Synthesis of Oxazoles and Imidazoles.
Article in Organic letters, 2017. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 9 papers.
What it found
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Trials whose registry record cites this paper, or whose number appears in the abstract. A trial that started after this paper was published is citing it as background, not reporting it.
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Who cites it
9 citing papers in PubMed, 41 citations in OpenAlex.
- Functionalized Polydopamine Nanoparticles: A Promising Drug Delivery Platform for the Treatment of Tuberculosis.Drug development research · 2025Review
- Photochemical three-component assembly of tri-substituted oxazoles through a carbenic phosphorus-nitrile hybrid ylide formation/trapping cascade.Chemical science · 2024Article
- New Strategies for the Functionalization of Carbonyl Derivatives via α-Umpolung: From Enolates to Enolonium Ions.Accounts of chemical research · 2023Article
- Sustainable Access to 5-Amino-Oxazoles and Thiazoles via Calcium-Catalyzed Elimination-Cyclization with Isocyanides.ChemSusChem · 2021Article
- Chemoselective α-Sulfidation of Amides Using Sulfoxide Reagents.Organic letters · 2020Article
- Synthesis of Novel Heterocycles by Amide Activation and Umpolung Cyclization.Organic letters · 2020Article
- Unified Approach to the Chemoselective α-Functionalization of Amides with Heteroatom Nucleophiles.Journal of the American Chemical Society · 2019Article
- α-Arylation of Carbonyl Compounds through Oxidative C-C Bond Activation.Angewandte Chemie (International ed. in English) · 2019Article
- Chemoselective Intermolecular Cross-Enolate-Type Coupling of Amides.Journal of the American Chemical Society · 2017Article
Corrections and comments
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Authors and funding
6 authors at 1 institution in 1 country.
Funding
Abstract
The preparation of substituted aminooxazoles and aminoimidazoles from α-arylamides and α-aminoamides through triflic anhydride-mediated amide activation is reported. These reactions proceed via the intermediacy of nitrilium adducts and feature N-oxide-promoted umpolung of the α-position of amides as well as a mechanistically intriguing sequence that results in sulfonyl migration from nitrogen to carbon. Quantum-chemical mechanistic analysis sheds light on the intricacies of the process.
Identifiers
What 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.