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.
A new synthetic entry to 3-carboxamido-4-carboxylic acid derivatives of isoxazole and pyrazole / C. Vicentini, M. Mazzanti, C. F. Morelli, M. Manfrini. - In: JOURNAL OF HETEROCYCLIC CHEMISTRY. - ISSN 0022-152X. - 37:1(2000), pp. 175-180.
A new synthetic entry to 3-carboxamido-4-carboxylic acid derivatives of isoxazole and pyrazole
C. F. Morelli;
2000
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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