ArticleACS omega2018
Theoretical Study on the Epimerization of Azlactone Rings: Keto-Enol Tautomerism or Base-Mediated Racemization?
Article in ACS omega, 2018. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 6 papers.
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Who cites it
6 citing papers in PubMed.
- Identification and Characterization of Antiviral Activity of Synthetic Compounds Against Mayaro Virus.Pharmaceuticals (Basel, Switzerland) · 2025Article
- Enantioselective organocatalytic strategies to access noncanonical α-amino acids.Chemical science · 2024Review
- Oxazolone mediated peptide chain extension and homochirality in aqueous microdroplets.Proceedings of the National Academy of Sciences of the United States of America · 2024Article
- Article
- Synthesis, In Silico and In Vitro Evaluation of Antimicrobial and Toxicity Features of New 4-[(4-Chlorophenyl)sulfonyl]benzoic Acid Derivatives.Molecules (Basel, Switzerland) · 2021Article
- On the Stability and Spectroscopic Properties of 5-Hydroxyoxazole-4-carboxylic Acid Derivatives.Organic letters · 2021Article
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Authors and funding
4 authors.
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Abstract
Azlactones are versatile heterocycles employed in a diversity of transformations; the main drawback of these cycles consists in the epimerization of the α-carbonyl stereocenter during its preparation. We hereby present a theoretical study to explain how the racemization occurs. Two hypotheses were investigated: the keto-enol tautomerism and the base-mediated racemization, through an enolate intermediate. The results showed that the latter is consistent with the experimental data and can spontaneously occur at room temperature. The same pathway was evaluated for 2-alcoxy azlactone, showing a slower epimerization ratio, consistent with the literature data.
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