Zur Reaktion von 4-Alkylaminodihydro-2(1H)-pyridinthionen bzw. -onen mit Ethylmalons�ure-bis-trichlorphenylester

Zigeuner, G.; Schweiger, Klaus; Habernig, Dietmar

doi:10.1007/bf00800264

Cited by 12 publications

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“…The con®guration of these isomers is directed both by the reaction conditions and the substitution at C-4. 4-Methylamino-5,6-dihydropyridin-2(1H)-one 3 [11] serves as starting material. Under Friedel-Crafts reaction conditions, the methylamino group of 3 is not attacked, and with acetyl chloride the 3-acetyl derivative 4 is obtained selectively.…”

Section: Resultsmentioning

confidence: 99%

Synthesis of Isomeric Isoxazolopyridinones

Weis

Schweiger

Fabian

1998

Monatshefte fuer Chemie

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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 con®gurations of the latter compounds were established by NMR experiments.

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