Chinese Journal of Organic Chemistry ›› 2022, Vol. 42 ›› Issue (5): 1501-1508.DOI: 10.6023/cjoc202201006 Previous Articles     Next Articles



张智鑫a, 翟彤仪a, 朱伯汉b, 钱鹏程b,*(), 叶龙武a,c,*()   

  1. a 厦门大学化学化工学院 福建厦门 361005
    b 温州大学化学和材料工程学院 浙江温州 325035
    c 中国科学院上海有机化学研究所 金属有机化学国家重点实验室 上海 200032
  • 收稿日期:2022-01-05 修回日期:2022-01-24 发布日期:2022-01-27
  • 通讯作者: 钱鹏程, 叶龙武
  • 作者简介:
  • 基金资助:

Synthesis of Tetrahydroindole Derivatives via Metal-Free Intramolecular [4+2] Annulation of Ynamides

Zhixin Zhanga, Tongyi Zhaia, Bohan Zhub, Pengcheng Qianb(), Longwu Yea,c()   

  1. a College of Chemistry and Chemical Engineering, Xiamen University, Xiamen, Fujian 361005
    b College of Chemistry & Materials Engineering, Wenzhou University, Wenzhou, Zhejiang 325035
    c State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai 200032
  • Received:2022-01-05 Revised:2022-01-24 Published:2022-01-27
  • Contact: Pengcheng Qian, Longwu Ye
  • About author:
    These authors contributed equally to this work
  • Supported by:
    National Natural Science Foundation of China(21772161)

A metal-free reaction of 4-siloxy-3,5-diene ynamides via an intramolecular [4+2] annulation has been developed. In the presence of catalytic Et3N, this protocol leads to the facile formation of six-membered cycloadducts. This reaction can proceed smoothly under mild condition without transition-metal-catalysts and its substrate scope is wide. This strategy provides a concise and practical protocol to synthesize natural product and bioactive compounds containing 4-hydroxyl hydroindole skeletons.

Key words: annulation reaction, metal-free catalysis, ynamides, heterocycle synthesis