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

✍ Scribed by Chiara B. Vicentini; Manuela Mazzanti; Carlo F. Morelli; Maurizio Manfrini

Book ID: 102342435
Publisher: Journal of Heterocyclic Chemistry
Year: 2000
Tongue: English
Weight: 409 KB
Volume: 37
Category: Article
ISSN: 0022-152X
DOI: 10.1002/jhet.5570370129

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✦ Synopsis

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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