Primary and secondary enaminones derived from cyclohexane-l,3-dione, dimedone, and acetylacetone react with cyclohexenone to give exclusively C-alkylated derivatives. In every case the products form carbinolamines which exist as 1hydroxy-2-azacyclo [3.3.1] nonenes. This was confirmed in some examples by formation of an extra ring between nitrogen and oxygen. A series of dienaminones were prepared from 2-(5,5-dimethyl-3-oxocyclohex-
The product of a Mannich reaction on butane-2.3-dione depended upon the secondary base employed. With dimethylamine the product was 2.4-bisdimethylaminomethyl-2-methylfuran-3(2H) -one (11). With morpholine or N-methylpiperazine, a bis Mannich base derived from 2.5-dimethylbenzene-1.4-diol was obtained while pyrrolidine was the only base investigated which gave the expected open chain bis Mannich derivative. P. H. B. Ingle, Ph.D. Thesis, University of Bradford, 1970.
Die Mannich‐Reaktion des Dions (I) mit Formaldehyd (II) ergibt in Äthanol in Gegenwart von Dimethylamin‐hydrochlorid das Furanon (III) als einziges Produkt.
Von Acetylaceton, Cyclohexan‐1,3‐ dion bzw. Dimedon abgeleitete Enaminone reagieren mit dem Cyclohexenon (II) ausschließlich unter C‐A1kylierung, wie z.B. die Enaminone (I) und (IV) zu den Aminolen (III) bzw. (V) [zum Beweis dient die thermische Cyclisierung von (Vd) zu dem Oxazolidin (VIII)].
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