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.

5-(Benzoyloxymethyl)isoxazole-3-carboxylic Acid Ethyl Ester / Cosimo Antonini, Franca Maria Cordero, Fabrizio Machetti. - In: MOLBANK. - ISSN 1422-8599. - ELETTRONICO. - 2024:(2024), pp. M1762.1-M1762.5. [10.3390/M1762]

5-(Benzoyloxymethyl)isoxazole-3-carboxylic Acid Ethyl Ester

Franca Maria Cordero;Fabrizio Machetti
2024

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.
2024
2024
1
5
Cosimo Antonini, Franca Maria Cordero, Fabrizio Machetti
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Utilizza questo identificatore per citare o creare un link a questa risorsa: https://hdl.handle.net/2158/1348235
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