3-苯基-2,3-二氢-1H-苯并[f]吲哚-4,9-二酮的合成研究  

Synthesis of 3-phenyl-2,3-dihydro-1H-benzo[f]indole-4,9-dione

作　　者：于雪[1] 徐小娜 柯苗 YU Xue;XU Xiao-na;KE Miao(School of Pharmaceutical&Chemical Engineering,Xianyang Vocational Technical College,Xianyang 712000,China)

机构地区：[1]咸阳职业技术学院医药化工学院,陕西咸阳712000

出　　处：《化学工程师》2022年第7期16-20,共5页Chemical Engineer

基　　金：咸阳职业技术学院博士科研基金项目(No.2021BK01);咸阳职业技术学院科学研究基金资助项目(No.2020KJB02)。

摘　　要：本文报道3-苯基-2,3-二氢-1H-苯并[f]吲哚-4,9-二酮(1a)的合成。以2-羟基萘-1,4-二酮(2)和(E)-硝基苯乙烯(3a)为原料,经过Michael加成、硝基还原两步反应合成得到目标化合物3-苯基-2,3-二氢-1H-苯并[f]吲哚-4,9-二酮(1a)。并分别对两步反应条件进行了考察,确定该Michael加成反应的适宜条件为:溶剂为二氯甲烷,物料比为n_(3a)∶n_(2)=1.1∶1,反应时间为2h,还原反应时间为8h。对该反应工艺的底物拓展发现,1-(3-甲氧苯基)-2-硝基乙烯(3b)同样适用于该反应条件,可用于制备3-(3-甲氧基苯基)-2,3-二氢-1H-苯并[f]吲哚-4,9-二酮(1b)。中间体及产物结构均经过^(1)H NMR、^(13)C NMR和ESI-MS表征确认。The synthesis of 3-phenyl-2,3-dihydro-1H-benzo[f]indole-4,9-dione(1a)was reported.The target compound(1a)was synthesized from 2-hydroxylnaphthalene-1,4-dione(2)and(E)-nitrostyrene(3a)by Michael addition and nitro reduction.The two steps reaction conditions were investigated,and the suitable conditions for the Michael addition reaction were determined as follows:solvent is dichloromethane,material ratio of n_(3a)∶n_(2)=1.1∶1,the reaction time is 2h,The reduction reaction time is 8h.The substrate expansion of the reaction process revealed that 1-(3-methoxyphenyl)-2-nitroethylene(3b)was also suitable for the preparation of 3-(3-methoxyphenyl)-2,3-dihydro-1H-benzo[f]indole-4,9-dione(1b).The structure of the intermediates and products were characterized by ^(1)H NMR、^(13)C NMR and ESI-MS.

关 键 词：苯并吲哚衍生物 苯并[f]吲哚-4 9-二酮 MICHAEL加成反应 还原反应 

分 类 号：TQ463[化学工程—制药化工]