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Chinese Journal of Organic Chemistry >

2023 , Vol. 43 >Issue 6: 2178 - 2188

DOI: https://doi.org/10.6023/cjoc202210037

Lewis Acid-Catalyzed [2+4] Cyclization of 3-Alkyl-2-vinylindoles with α,β-Unsaturated N-Sulfonyl Ketimines

  • Lixing Sun ,
  • Tingting Sun ,
  • Haiqing Wang ,
  • Shufang Wu ,
  • Xiaoye Wang ,
  • Tianya Liu ,
  • Yuchen Zhang
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  • a School of Chemistry and Materials Science, Jiangsu Normal University, Xuzhou, Jiangsu 221116
    b Department of Anesthesiology, The Affiliated Hospital of Xuzhou Medical University, Xuzhou, Jiangsu 221004
    c Key Laboratory of Anesthesiology of Jiangsu Province, Xuzhou Medical University, Xuzhou, Jiangsu 221004
† These authors contributed equally to this work
* E-mail: ;

Received date: 2022-10-29

  Revised date: 2022-12-10

  Online published: 2022-12-28

Supported by

National Natural Science Foundation of China(22101103); Natural Science Foundation of Jiangsu Province(BK20201018); High-level Innovative and Entrepreneurial Talents Introduction Plan of Jiangsu Province, the Technology Plan of Xuzhou City(KC21021); Undergraduate Students Project of Jiangsu Province(202110320041Z)

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Abstract

A Lewis acid-catalyzed [2+4] cyclization of 3-alkyl-2-vinylindoles with α,β-unsaturated N‑sulfonyl ketimines was established, and indole-containing piperidines with potential antitumor activity were synthesized in moderate to good yields (up to 95% yield) and generally excellent diastereoselectivities (up to>95:5 dr). This work has confronted the challenges in exploring the [2+4] cyclization of 3-alkyl-2-vinylindoles, which will enrich the chemistry of 3-alkyl-2-vinylindoles. In addition, this approach provides an atom-economic method for the synthesis of indole-containing piperidines.

Key words： 3-alkyl-2-vinylindole; α,β-unsaturated N-sulfonyl ketimine; [2+4] cyclization; indole derivative

Cite this article

Lixing Sun , Tingting Sun , Haiqing Wang , Shufang Wu , Xiaoye Wang , Tianya Liu , Yuchen Zhang . Lewis Acid-Catalyzed [2+4] Cyclization of 3-Alkyl-2-vinylindoles with α,β-Unsaturated N-Sulfonyl Ketimines[J]. Chinese Journal of Organic Chemistry, 2023 , 43(6) : 2178 -2188 . DOI: 10.6023/cjoc202210037

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