| Autor: |
Cosimo Antonini, Franca M. Cordero, Fabrizio Machetti |
| Jazyk: |
angličtina |
| Rok vydání: |
2024 |
| Předmět: |
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| Zdroj: |
Molbank, Vol 2024, Iss 1, p M1762 (2024) |
| Druh dokumentu: |
article |
| ISSN: |
1422-8599 |
| DOI: |
10.3390/M1762 |
| Popis: |
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. |
| Databáze: |
Directory of Open Access Journals |
| Externí odkaz: |
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