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Research on heterocyclic compounds. XIII. Synthesis of 4,5‐dihydro‐5‐oxo‐3‐isoxazoleacetic acid and related compounds
Author(s) -
Abignente Enrico,
De Caprariis Paolo,
Liguori Michele
Publication year - 1983
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.5570200633
Subject(s) - chemistry , diazomethane , hydroxylamine , organic chemistry , derivative (finance) , ammonia , liquid ammonia , elemental analysis , medicinal chemistry , financial economics , economics
Some new 4,5‐dihydro‐5‐oxoisoxazole derivatives were synthesized as part of a study to prepare potential antiinflammatory agents. The reaction of the diethyl ester of 3‐oxopentanedioic acid with hydroxylamine afforded the 3‐hydroxyimino derivative, which was then cyclized to the title compound. This reacted with diazomethane to give a couple of isomeric methyl derivatives, namely methyl 2,5‐dihydro‐2‐methyl‐5‐oxo‐3‐isoxazoleacetate and methyl 5‐methoxy‐3‐isoxazoleacetate. Reaction of these compounds with ammonia gave the corresponding acetamides. All compounds were characterized by elemental analysis, uv, ir, and 1 H‐nmr spectra.