Reaction of 1-substituted 3-(2-hydroxyethylamino)quinoline-2,4(1H,3H)-diones with isothiocyanic acid

3-Chloroquinoline-2,4-diones react with ethanolamine to form 3-(3-hydroxyethylamino)quinoline-2,4-diones. These compounds afford, depending on substituents in positions 1 and 3, four different products from their reaction with isothiocyanic acid: 3-(2-hydroxyethyl)-2-thioxo-3,3a-dihydro-1H-imidazo[4,5-c]quinolin-4(5H)-ones, 9b-hydroxy-3-(2-hydroxyethyl)-2-thioxo-3,3a,5,9b-tetrahydro-1Himidazo[4,5-c]quinolin-4(2H)-ones, 3-(2-hydroxyethyl)-2-thioxo-2,3-dihydro-1H-imidazo[4,5-c]quinolin-4(5H)-ones, or 1′-methyl-7a-phenyl-5-thioxo-3,5,6,7a-tetrahydro-2H-spiro[imidazo[5,1-b]oxazole-7,3′-indolin]-2′-one.

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A. K. and M. R. thank for financial support from the internal grant of TBU in Zlín (No. IGA/FT/2019/010), funded from the resources of specific university research. The authors thank Mrs. H. Geržová (Faculty of Technology, Tomas Bata University in Zlín) for technical help.

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Correspondence to Antonín Klásek.

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Published in Khimiya Geterotsiklicheskikh Soedinenii, 2020, 56(5), 566–571

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Klásek, A., Lyčka, A., Rouchal, M. et al. Reaction of 1-substituted 3-(2-hydroxyethylamino)quinoline-2,4(1H,3H)-diones with isothiocyanic acid. Chem Heterocycl Comp 56, 566–571 (2020). https://doi.org/10.1007/s10593-020-02701-9

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Keywords

  • isocyanic acid
  • isothiocyanic acid
  • 2-thioxo-1H-imidazo[4,5-c]quinolin-4(2H)-ones
  • 2-thioxo-1H-imidazo[4,5-c]quinolin-4(5H)-ones
  • quinoline-2,4-diones
  • nuclear magnetic resonance
  • rearrangement