中南大学学报（自然科学版）2018，Vol.49Issue(5)：1062-1071,10.DOI:10.11817/j.issn.1672-7207.2018.05.006
邻亚甲基醌和3-氯吲哚啉酮[4+1]环加成合成螺环吲哚啉酮
Synthesis of spirooxindoles through [4+1] cycloaddition of ortho-quinone methides with 3-chlorooxindoles
摘要
Abstract
The spirooxindoles were synthesized in high yield with excellent diastereoslectivities using 3-chlorooxindoles and ortho-quinone methides(o-QMs)as materials through the Michael addition/cyclization cascade process under basic condition. To get the two spirocyclic compound involving benzofuran and oxindole skeletons under mild and easy-handle conditions,3-chlorooxindoles was introduced to react with the o-QMs, which were synthesized in situ from 2-(1-tosylalkyl) phenols. And the optimized target products were obtained through condition selection. The gram-scale experiments were conducted to verify the practicality of this method. The results show that under optimized condition, the yield of target product can achieve 92% and the diastereoselectivity dris more than 20:1. And high yield and diastereoselectivity can be maintained when the substrate amount increases. The method can be applied widely and multiple compounds such as 2-(1-tosylalkyl) phenols and 3-chlorooxindoles can be used as materials in this method.关键词
3-氯吲哚啉酮/邻亚甲基醌中间体/Michael加成/环化串联反应/螺环吲哚啉酮化合物Key words
3-chlorooxindole/ortho-quinone methides/Michael addition/cyclizaiton/spirooxindoles分类
化学化工引用本文复制引用
杜升华,周吉,江国防..邻亚甲基醌和3-氯吲哚啉酮[4+1]环加成合成螺环吲哚啉酮[J].中南大学学报（自然科学版）,2018,49(5):1062-1071,10.基金项目
国家自然科学基金资助项目(51578224)(Project(51578224)supported by the National Natural Science Foundation of China) （51578224）
