C2或C3-环庚三烯基取代的吲哚化合物的快速合成

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

摘要

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.

Abstract

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.

关键词

环庚三烯 / 吲哚 / 卓鎓离子 / 合成

Key words

cycloheptatriene / indole / tropylium / synthesis

基金资助

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)