2-苯氧(硫)甲基-6,7-亚甲二氧-3-喹啉酸乙酯及其衍生物的合成  

Synthesis of Ethyl 2-Phenoxy (thio) methyl-6, 7-MethyIenedioxy-3-Quinolinecarboxylate and Its Derivatives

作　　者：杨定乔 高永俊[2] 姜贵吉[2] 

机构地区：[1]黄冈师范专科学校化学系,湖北黄冈436100 [2]延边大学化学系,吉林延吉133002

出　　处：《有机化学》1994年第6期626-629,共4页Chinese Journal of Organic Chemistry

摘　　要：抗疟药物中有不少取代喹啉衍生物,本文报道2—溴甲基—6,7—亚甲二氧—3—喹啉酸乙酯(2)与取代酚反应所生成的喹啉衍生物3a～g。 结果与讨论 首先利用6—氨基胡椒醛与乙酸乙酸乙酯在乙醇钠的催化下缩合,得到化合物l,l与NBS反应,经柱层析分离证实,R_f为0.81是原料1,R_f为0.41是2,2与苯酚,取代苯酚,苯硫酚,取代苯硫酸发生Williamson取代反应,得到一系列喹啉酚醚衍生物3a～g。The Base-Catalyzed Condensation of 6-aminopiperonal with ethyl acetoacetate followed by bromination with NBS gave ethyl 2-bromomethyl-6,7-methylenedioxy-3-quino-linecarboxylate (2). Williamson reaction of 2 with un- and substituted phenol or thiothenol yielded ethyl 2-(un) substituted phenoxy (thioxy) methyl-6,7-methylenedioxy-3-quinoline-carboxylate (3a-g) in excellent yields Electron-withdrawing group at the phenol or thiothenol ring was favorable for the formation of the nucleophile and Williamson reaction.

关 键 词：喹啉酸乙酯 衍生物 合成 

分 类 号：O623.624[理学—有机化学]