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Ball-milling Synthesis of Tetrahydroquinolines via ‘One-pot’ Three-component Diels-Alder Reaction Catalyzed by Phosphotungstic Acid

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Abstract

We reported an economic and practical ball-milling method for the synthesis of tetrahydroquinoline derivatives via a ‘one-pot’ three-component Diels-Alder reaction of anilines, aldehydes and alkenes catalyzed by phosphotungstic acid at room temperature. For this reaction, a simple “one-pot” ball-milling operation was conducted, readily available starting materials were employed, ‘one-pot’ conditions were applied, and the most important was to use inexpensive and environmentally friendly catalyst phosphotungstic acid. Various tetrahydroquinolines, which might be potentially applicable in the pharmaceutical and biochemical areas, were conveniently synthesized in moderate to excellent yields.

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Article Open access 02 December 2021

Baoxin Zhang, Dilver Peña Fuentes & Armin Börner

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Authors and Affiliations

  1. School of Chemistry and Chemical Engineering, Liaocheng University, Liaocheng, 252000, P. R. China

    Zeyou Wang, Guodong Shen, Xianqiang Huang, Shuwen Gong, Bingchuan Yang, Zhenzhen Sun & Zuhao Zhang

  2. Department of Chemistry, Liaocheng Chemical Institute of Industrial Science, Liaocheng, 252000, P. R. China

    Wanxing Liu

Authors
  1. Zeyou Wang
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  2. Guodong Shen
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  3. Xianqiang Huang
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  4. Shuwen Gong
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  5. Bingchuan Yang
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  6. Zhenzhen Sun
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  7. Zuhao Zhang
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  8. Wanxing Liu
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Corresponding authors

Correspondence to Guodong Shen or Xianqiang Huang.

Additional information

Supported by the Natural Science Foundation of Shandong Province, China(Nos.ZR2019QB022, ZR2019MB043).

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Wang, Z., Shen, G., Huang, X. et al. Ball-milling Synthesis of Tetrahydroquinolines via ‘One-pot’ Three-component Diels-Alder Reaction Catalyzed by Phosphotungstic Acid. Chem. Res. Chin. Univ. 36, 835–842 (2020). https://doi.org/10.1007/s40242-020-9019-3

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  • DOI: https://doi.org/10.1007/s40242-020-9019-3

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