Photodimerisation of Amidopyrine [1,2] An Example of [2+2] Photocycloaddition of an Enamine-Like Structure

Reisch, J.; Abdel-Khalek, Magdi M.

doi:10.1515/znb-1979-1017

Cited by 3 publications

References 7 publications

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Photochemische Abbauwege des Amino‐ und Hydroxyphenazons in Aceton

Reisch

Abdel-Khalek

1983

Archiv der Pharmazie

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Der photochemische Abbau des Aminophenazons fiihrt in Aceton zum 2-(l-Methyliminoethyl)-4-oxo-pent-2-ensaureanilid (7), 6-Methyl-2-(1-methylimino-ethyl)-4-oxo-hepta-2,5-diensaureanilid (9), N,N-Dimethyl-N'-phenyloxamid (10) und N,N-Dimethyl-N'-phenylharnstoff (11). In Acetonitril entstehen neben den beiden letztgenannten Produkten noch Oxanilid und N-Methyl-N'-phenyloxanid. Bei der Photolyse von Hydroxyphenazon in Aceton bildet sich 6-Methyl-2-( 1 -me thylimino-ethyl)-4-oxo-hepta-2,5-diensaureanilid, Oxanilid und N-Methyl-N'-phenyloxamid. Der Zerfallsmechanismus wird diskutiert. Photodegradation of Aminoand Hydroxyphenazone in AcetoneThe photochemical degradation of aminophenazone in acetone leads to 2-[ 1-(methylhino)-ethylJ-4-oxopent-2-enoic anilide (7), 6-methyl-2-fl-(methylimino)ethyl]-4-oxohepta-2,5-dienoic anilide (9), N, N,-dimethyl-N-phenyl oxamide (10) and N,N-dimethyl-N-phenylurea (11). In addition to the last two products, oxanilide and N-methyl-N-phenyl oxamide are obtained, when the irradiation is carried out in acetonitrile. 6-Methyl-2-[l-(methylimino)ethyl]-4-oxohe~ta-2,5-dienoic anilide, oxanilide and N-methyl-N'-phenyl oxamide are formed as a result of hydroxyphenazone photolysis in acetone. The degradation mechanism is discussed.i . 42. Mitt.: Photo-und Strahlenchemische Studien, 41.

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