A new synthetic entry to 3-carboxamido-4-carboxylic acid derivatives of isoxazole and pyrazole |
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| Authors: | Chiara B Vicentini Manuela Mazzanti Carlo F Morelli Maurizio Manfrini |
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| Institution: | Dipartimento di Scienze Farmaceutiche, Università degli Studi, 44100 Ferrara, Italy |
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| Abstract: | Ethyl 2-amino-3-methoxycarbonyl-4-oxo-2-pentenoate (3) reacts with hydroxylamine or hydrazines to give isoxazole and pyrazole ortho-dicarboxylic acid esters 4 and 5, respectively. Partial hydrolysis of diesters 4 and 5 afforded the corresponding dicarboxylic acid monoesters 6 and 7. Amidation of the intermediate acid chlorides 8,9 followed by hydrolysis of 4-methylesters 10, 11 gave the title compounds 1 and 2, respectively. |
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