Chinese Journal of Organic Chemistry ›› 2023, Vol. 43 ›› Issue (9): 3226-3238.DOI: 10.6023/cjoc202302018 Previous Articles     Next Articles


贝文峰, 潘健, 冉冬梅, 刘伊琳, 杨震*(), 冯若昆*()   

  1. 绍兴文理学院化学化工学院 浙江省精细化学品传统工艺替代技术研究重点实验室 浙江绍兴 312000
  • 收稿日期:2023-02-16 修回日期:2023-05-10 发布日期:2023-05-23
  • 基金资助:
    浙江省自然科学基金(LQ15B020002); 绍兴市科技计划(2018C10017); 国家级大学生创新创业训练计划(202110349018); 国家级大学生创新创业训练计划(202210349010); 浙江省教育厅科研计划(Y202043097)

Cobalt-Catalyzed [4+2] Annulation of Indole Carboxamide with Diynes and Monoacetylene: Direct Access to γ-Carbolinones

Wenfeng Bei, Jian Pan, Dongmei Ran, Yilin Liu, Zhen Yang(), Ruokun Feng()   

  1. Zhejiang Key Laboratory of Alternative Technologies for Fine Chemicals Process, College of Chemistry and Chemical Engineering, Shaoxing University, Shaoxing, Zhejiang 312000
  • Received:2023-02-16 Revised:2023-05-10 Published:2023-05-23
  • Contact: E-mail:;
  • Supported by:
    Zhejiang Provincial Natural Science Foundation(LQ15B020002); Shaoxing Science and Technology Plan(2018C10017); National College Students' Innovation and Entrepreneurship Training Program(202110349018); National College Students' Innovation and Entrepreneurship Training Program(202210349010); Scientific Research Program of Zhejiang Provincial Education Department(Y202043097)

A cobalt-catalyzed annulation of the C(sp2)—H/N—H bond of 3-indolecarboxamides with alkynes assisted by 8-aminoquinoline is reported for the preparation of γ-carbolinones. The research results indicated that under the optimal reaction conditions, the isolated yield was up to 90% with Co(acac)2 (10 mol%) as catalyst, Mn(acac)3 (1.0 equiv.) as oxidant, NaOPiv (2.0 equiv.) as base, trifluoroethanol (2.0 mL) as solvent at 120 ℃ for 24 h. The protocol has a broad scope for alkynes. Both 1,4-diarylbuta-1,3-diynes and dialkyl diynes could react with N-(quinolin-8-yl)-1H-indole-3-carboxamide, giving the desired products in moderate to good yield. It was noteworthy that terminal and internal alkynes were found to be applicable to this transformation, affording the γ-carbolinones in good yield and high selectivity. This method has the advantages of applying cheap and commercially available cobalt and manganese salts as the catalytic system, requiring no additional ligands and indole nitrogen protecting groups, providing a new method for the synthesis of γ-carbolinone compounds with wide application value.

Key words: cobalt-catalysis, indole carboxamide, alkynes, [4+2] annulation, γ-carbolinones