| Abstrakt: |
By the action of ammonium acetate and a,ß-unsaturated carbonyl compounds, 1,5-diketones of the indolinone series undergo not yet known transformations into difficultly accessible 1,2-dihydro-10H-quinodolines. Under these conditions, 11-phenyl-1,2,3,4-tetrahydro-10H-quindoline was obtained from 1-acetyl-2-(benzyl-cyclohexan-1-on-a-yl)indolin-3-one. Dihydroquindolines with identical aryl substituents in the 1- and 11-positions were obtained from 1-acetylindolin-3-one by the action of an excess of certain a,ß-unsaturated ketones and ammonium acetate. Dehydrogenation of dihydroquindolines proceeds smoothly on heating with sulfur. The possible paths of the formation of dihydroquindolines are discussed. |
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