3,4-二氢二苯[f,h]异喹啉-1-酮的合成  

Preparation of 3,4-dihydrodibenzo [f,h]Isoquinolin-1(2H)-one

作　　者：粟立丹[1] 戢得蓉[1] 张成刚[1] 

机构地区：[1]四川师范大学化学与材料科学学院,四川成都610066

出　　处：《四川师范大学学报（自然科学版）》2013年第6期921-924,共4页Journal of Sichuan Normal University（Natural Science）

基　　金：国家自然科学基金(21072141);四川省教育厅自然科学重点基金(12ZA141)资助项目

摘　　要：娃儿藤生物碱具有显著的抗炎、抗肿瘤等生物活性,为研究其二苯并四氢异喹啉衍生物(1)的抗肿瘤活性,以邻苯二甲酸酐和β-氨基丙酸等为起始原料,经5步反应,合成前体化合物3,4-二氢二苯[f,h]异喹啉-1-酮(2).先由化合物3在多聚磷酸作用下经傅克酰基化反应得到中间体4,4酸水解后,与4-甲氧基苯乙酸发生亲核取代反应得中间体5,5在碱性条件下发生分子内缩合反应制得中间体6,最后经2,3-二氯-5,6-二氰对苯醌(DDQ)氧化偶联得2.该合成反应条件温和,但因竞争反应即消除反应导致6的产率低.The biological properties of tylophorine alkaloids range from anti-inflammatory to anti-cancer.In order to investigate the antitumour activity of 1,2,3,4-tetrahydrodibenzo [f,h] isoquinoline （1）,its precursor 3,4-dihydrodibenzo [f,h] isoquinolin-1 （2H）-one （2） was synthesized via five-step reactions using phthalic anhydride and [β-alanine as raw materials.In the procedure,compound 4 was synthesized by the Friedel-Crafts reaction in the presence of PPA.And then,the intermediate 5 was synthesized by acid hydrolysis reaction and nucleophilic substitution reaction.Intramolecular condensation of 5 in 5％ KOH/EtOH gave intermediate 6.Finally,compound 2 was formed by oxidative coupling reaction using DDQ.The synthetic conditions were mild.But the yield was poor due to elimination reaction of 5,completing with its expected condensation reaction.

关 键 词：3 4-二氢二苯[f h]异喹啉-1-酮 分子内缩合 氧化偶联 DDQ 

分 类 号：O623.42[理学—有机化学]