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- Title
5-(Benzoyloxymethyl)isoxazole-3-carboxylic Acid Ethyl Ester.
- Authors
Antonini, Cosimo; Cordero, Franca M.; Machetti, Fabrizio
- Abstract
We describe here the palladium hydrogenation of ethyl 5-(benzoyloxymethyl)isoxazole-3-carboxylate. The presence of two reducible sites in the molecule, namely the benzylic-like position and the isoxazole N–O bond, creates a possible competition. The results show that under the applied conditions, ethyl (Z)-2-amino-4-oxo-2-pentanoate is obtained as the only product. Accordingly, a domino process occurs, consisting of deoxygenation to the 5-methylisoxazole derivative followed by reductive opening of the isoxazole ring. The isoxazole substrate was prepared by NaOH-catalyzed cycloaddition-condensation of ethyl nitroacetate and propargyl benzoate in water. Complete characterizations of the isoxazole and Z-enaminone derivatives are reported.
- Subjects
ETHYL esters; ISOXAZOLES; DEOXYGENATION; HYDROGENATION; NITRO compounds; PALLADIUM; RING formation (Chemistry); ACETATES
- Publication
Molbank, 2024, Vol 2024, Issue 1, pM1762
- ISSN
1422-8599
- Publication type
Article
- DOI
10.3390/M1762