4-(1,2-亚乙二氧基)环己酮及其2-甲醛和2-羧酸酯的烯胺和烯醇反应的研究

Studies on the Reactions of the Enamines and Enols of 4, 4-Ethylenedioxo-cyclohexanone and Its 2-Carbaldehyde and 2-Carboxylic Ester

4-(1,2-亚乙二氧基)环己酮及其2-甲醛和2-羧酸酯的烯胺和烯醇与丙烯酸型的和丙二酸型的试剂反应,获得了与6-(1,2-亚乙二氧基)-5,6,7,8-四氢-2(1H)-喹啉酮很相近的四个化合物(5、11、18、19)和六个其它化合物(4、7、8、9、16、17)。探讨了这十个均未见于文献的新化合物的生成机理,并得到一个制备5-四氢萘胺衍生物的新方法。

In order to prepare some carboxylic and hydro derivatives of 6, 6-ethylenedioxo-5, 6, 7, 8-tetrahydro-2(1H)-quinolinone (1), 4, 4-ethyienedioxo-cyclohexanone (3) and its 2-carbaldehyde (12) and 2-carboxylic ester (2) were taken on trials to react with some acrylo and malone reagents.Ethyl 4, 4-ethylenedioxo-cyclohexanone-2-carboxylate (2) in its enolate 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 and meldrum acid.Thus, ten new compounds, of which one hexa-hydro-2(1H)-quinolinone(11), three tetra- and hexa-hydro-2 (1H)-quinolinone carboxylic 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 cyanoethylated compound (4), were obtained. At the same time, the formation mechanisms of the bicycle compounds and 5-aminotetralins were proposed, and a new synthetic method of 5-aminotetralin analogs was established.