喹啉二酮类化合物的合成研究——形成双(二氢喹啉二酮基)甲烷的可能途径

SYNTHETIC STUDY ON QUINOLINEDIONE ANALOGUES——POSSIBLE INTERPRETATION FOR FORMATION OF 3,3'-METHYLENE-BIS-4-HYDROXY-2-QUINOLONES

我们曾用2-(3-甲基丁烯-2-基)丙二酸二乙酯与 N-取代芳胺在高温下环合,制备了一系列4-羟基-3-(3-甲基丁烯-2-基)二氢喹啉-2-酮类化合物.在此反应中除得到正常产物外,尚分离到若干副产物,最主要的副产物为3,3′-双(二氢喹啉-2,4-二酮基)甲烷.Young 等人曾对产生这类副产物的机理作过讨论,并提出如下途径:

In the course of condensation of arylamines with diethyl 3-methyl-2-butenylmalonate to give 4-hydroxy-3-(3-methyl-2-butonyl)-2-quinolones(1),we isolated theunexpected product,3,3-methylene-bis-4-hydroxy-2-quinolones(6).The mechanismfor the formation of the latter was proposed by Young previously.Our experiments didnot confirm his explanation and two possible reaction mechanisms have been proposed.The difference is in forming the intermediate 10 or 5 which is not produced via theretro-Mannich reaction presented by Young.