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Chinese Journal of Organic Chemistry >

2022 , Vol. 42 >Issue 5: 1501 - 1508

DOI: https://doi.org/10.6023/cjoc202201006

ARTICLES

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

  • Zhixin Zhang ,
  • Tongyi Zhai ,
  • Bohan Zhu ,
  • Pengcheng Qian ,
  • Longwu Ye
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  • 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
†These authors contributed equally to this work
*Corresponding authors. E-mail: ;

Received date: 2022-01-05

  Revised date: 2022-01-24

  Online published: 2022-01-27

Supported by

National Natural Science Foundation of China(21772161)

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Abstract

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

Cite this article

Zhixin Zhang , Tongyi Zhai , Bohan Zhu , Pengcheng Qian , Longwu Ye . Synthesis of Tetrahydroindole Derivatives via Metal-Free Intramolecular [4+2] Annulation of Ynamides[J]. Chinese Journal of Organic Chemistry, 2022 , 42(5) : 1501 -1508 . DOI: 10.6023/cjoc202201006

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