Facile synthesis of C2 or C3-(cycloheptatrienyl)-substituted indoles  

C2或C3-环庚三烯基取代的吲哚化合物的快速合成

作　　者：PANG Jinyu YAO Chunna WU Bin 庞进语;姚春娜;吴滨(中南民族大学药学院,武汉430074;中南民族大学学报编辑部,武汉430074)

机构地区：[1]South-Central Minzu University,School of Pharmaceutical Sciences,Wuhan 430074,China [2]South-Central Minzu University,Editorial Department of Journal,Wuhan 430074,China

出　　处：《中南民族大学学报(自然科学版)》2025年第2期201-212,共12页Journal of South-Central Minzu University(Natural Science Edition)

基　　金：国家自然科学基金资助项目(21772236);中央高校基本科研业务费专项资金资助项目(YJS22119)。

摘　　要：Cycloheptatriene is a privileged structural motif present in many bioactive compounds,pharmaceutical agents and natural products,especially in a large number of core structures of sesquiterpenoids.Herein,a mild and efficient synthetic approach was reported for access of a series of C2 or C3-(cycloheptatrienyl)-substituted indoles.A wide range of functional groups can be well tolerated in this transformation,especially including hydroxyl,halo,carboxylic acid and its derivative groups.Based on these results,a rational mechanism via electrophilic substitution of indoles with tropylium tetrafluoroborate is proposed.环庚三烯作为一种特殊的结构单元,广泛存在于倍半萜的核心骨架中,是许多药物活性化合物,药物分子和天然产物的重要组成部分.新发现一种在温和条件下高效地合成C2或C3-环庚三烯基取代的吲哚化合物的方法,该方法对各种官能团具有很好的兼容性,特别是当底物中含有羟基、卤素、羧酸及其衍生物等官能团时,实验结果表明,反应仍然能高收率地得到目标产物.通过反应机理分析,推测该反应是通过吲哚与卓鎓阳离子的亲电取代反应发生的.

关 键 词：cycloheptatriene INDOLE TROPYLIUM SYNTHESIS 

分 类 号：O621.3[理学—有机化学]