Summary.
Reaction of 4-methylamino-5,6-dihydropyridinone with acetyl chloride yielded exclusively the 3-acetyl derivative. When the methylamino group of the latter was removed by alkaline hydrolysis, a mixture of two hydroxy derivatives was formed. Those cyclized upon treatment with hydroxylamine exclusively to the isoxazolo[4,5-c]pyridinone, whereas the 4-methylamino analogue yielded, depending on pH, mainly the isoxazolo[4,3-c]pyridinone or the isoxazolo[4,5-c]pyridinone. The configurations of the latter compounds were established by NMR experiments..
Zusammenfassung.
Bei der Umsetzung von 4-Methylamino-5,6-dihydropyridinon mit Acetylchlorid entstand ausschließlich das 3-Acetylderivat. Bei der alkalischen Hydrolyse der Methylaminogruppe entstand ein Gemisch zweier Hydroxyderivate. Diese reagieren mit Hydroxylamin zum Isoxazolo[4,5-c]pyridinon, während das 4-Methylaminoanaloge in Abhängigkeit vom pH-Wert zum Isoxazolo[4,3-c]pyridinon oder zum Isoxazolo[4,5-c]pyridinon cyclisiert. Die Konfiguration der letzteren Verbindungen wurde durch NMR-Messungen gesichert..
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Received July 3, 1998. Accepted (revised) July 24, 1998
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Weis, R., Schweiger, K. & Fabian, W. Synthesis of Isomeric Isoxazolopyridinones. Monatshefte fuer Chemie 129, 1285–1292 (1998). https://doi.org/10.1007/PL00010140
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DOI: https://doi.org/10.1007/PL00010140