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Aliphatic, cycloaliphatic and heteroaromatic tert. Amines react with 2,4-dioxo-1-phenyl-1,2,3,4-tetrahydroquinoline-3-spiro-2′-oxiran (1) at 20 °C to give the betaines 2a−g, of which 2a−c are thermically rearranged to 3,4-methylendioxy-1-phenyl-1,2- dihydro-2-quinolone (3). The thermolysis of 2g yields 3-(4-dimethylamino-pyridinio)-2-oxo-1-phenyl-1,2-dihydroquinoline-4-olat (4).

zeitschrift für naturforschung b

Betaine als Zwischenprodukte der Umlagerung eines Spiro-oxirans in ein Dioxolen / Betaines as Intermediates in the Rearrangement of a Spiro-oxiran into a Dioxolen