STUDIES ON THE REACTIONS OF THE ENAMINES AND ENOLS OF 4,4-ETHYLENEDIOXO-CYCLOHEXANONE AND ITS 2-CARBALDEHYDE AND 2-CARBOXYLIC ESTER

In order to prepare some carboxylic and hydro derivatives of 6, 6-ethy lenedioxo-5, 6, 7, 8-tetrahydro-2(1H)-quinolinone (1), 4, 4-ethylenedi oxo-cyclohexanone (3) and its 2-carbaldehyde (12) and 2-carboxylic est er (2) were taken on trials to react with some acrylo and malono reage nts. Ethyl 4, 4-ethylenedioxo-cyclohexanone-2-carboxylate (2) in its e nolate form was subjected to react with acrylonitrile, acryloamide and 2-bromoacryloamide, and, 4, 4-ethylenedioxo-cyclohexanone (3) in its enamine form (10) with acryloamide, 4, 4-ethylenedioxo-cyclohexanone-2 -carbaldehyde (12) in its keto-enamine form (13) with cyanoacetamide a nd meldrum acid. Thus, ten new compounds, of which one hexa-hydro-2(1H )-quinolinone (11), three tetra- and hexa-hydro-2(1H)-quinolinone carb oxylic acids and derivatives (18, 19, 5), three 9-oxa-bicyclo-[4.3.0]- 1-nonenes (7, 8, 9), two 5-aminotetralins (16, 17), and one cyanoethyl ated compound (4), were obtained. At the same time, the formation mech anisms of the bicycle compounds and 5-aminotetralins were proposed, an d a new synthetic method of 5-aminotetralin analogs was established.