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Transformation of 2-Azaquinolizidone-1 N-oxides into Enamine Lactams
Thiel, Jacek
, p. 423 - 430 (2007/10/02)
Hitherto-unknown 2-azaquinolizidone-1 N-oxides IIa and IIb have been synthesized in order to observe the effect of the lactam carbonyl group on the properties of the N-oxide function formed on the bridgehead N atom of bicyclic amine.These N-oxides under the effect of aqueous NaOH and KOH solutions undergo transformation into enamine lactams Va and Vb.It is supposed that the distribution in compounds IIa and IIb of the N -> O group(s) and the lactam carbonyl group in position 1-3 facilitates the abstractions of the proton situated between them, thus giving rise to the reaction II -> V.The transformation described presents a new type of splitting of the N -> O function which occurs under the effect of hydroxide anions.
