A new synthetic entry to 3‐carboxamido‐4‐carboxylic acid derivatives of isoxazole and pyrazole | Zendy

Vicentini Chiara B. | Zendy; Mazzanti Manuela | Zendy; Morelli Carlo F. | Zendy; Manfrini Maurizio | Zendy

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A new synthetic entry to 3‐carboxamido‐4‐carboxylic acid derivatives of isoxazole and pyrazole

Author(s) -

Vicentini Chiara B.,

Mazzanti Manuela,

Morelli Carlo F.,

Manfrini Maurizio

Publication year - 2000

Publication title -

journal of heterocyclic chemistry

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 0.321

H-Index - 59

eISSN - 1943-5193

pISSN - 0022-152X

DOI - 10.1002/jhet.5570370129

Subject(s) - isoxazole , chemistry , pyrazole , hydroxylamine , hydrolysis , carboxylic acid , dicarboxylic acid , organic chemistry

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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