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

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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Correspondence to Guodong Shen or Xianqiang Huang.

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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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Keywords

  • Ball-milling
  • Diels-Alder reaction
  • Phosphotungstic acid
  • Tetrahydroquinoline