One-Pot Synthesis of N-(Phosphorylmethyl)Pyrrolidines via Acid-Catalyzed Cascade Elimination/Cyclization/Friedel–Crafts Reaction

The efficient approach to novel water-soluble 2-aryl-substituted N-(phosphorylmethyl)pyrrolidines via acid-catalyzed elimination/cyclization/Friedel–Crafts reaction sequence of {[(4,4-diethoxybutyl)amino]methyl}phosphonates is proposed. Zwitterionic structure of N-(phosphorylmethyl) pyrrolidines has been proved by X-ray crystallography.

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Figure 1
Scheme 1
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Scheme 2

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Correspondence to Liliya I. Vagapova.

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Published in Khimiya Geterotsiklicheskikh Soedinenii, 2020, 56(5), 542–547

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Vagapova, L.I., Burilov, A.R., Gazizov, A.S. et al. One-Pot Synthesis of N-(Phosphorylmethyl)Pyrrolidines via Acid-Catalyzed Cascade Elimination/Cyclization/Friedel–Crafts Reaction. Chem Heterocycl Comp 56, 542–547 (2020). https://doi.org/10.1007/s10593-020-02697-2

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Keywords

  • aminophosphonate
  • pyrrolidine
  • cyclization
  • heterocycle