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) Kafka, S.; Klásek, A.; Polis, J.; Košmrlj, J. Heterocycles2002, 57, 1659. (b) Klásek, A.; Kořistek, K.; Lyčka, A.; Holčapek, M. Tetrahedron2003, 59, 1283. (c) Klásek, A.; Kořistek, K.; Lyčka, A.; Holčapek, M. Tetrahedron2003, 59, 5279. (d) Klásek, A.; Lyčka, A.; Holčapek, M. Tetrahedron2007, 63, 7059. (e) Klásek, A.; Lyčka, A.; Holčapek, M.; Hoza, I. Helv. Chim. Acta2008, 91, 354. (f) Prucková, Z.; Klásek, A.; Lyčka, A.; Mikšík, I.; Růžička, A. Tetrahedron2009, 65, 9103. (g) Mrkvička, V.; Lyčka, A.; Rudolf, O.; Klásek, A. Tetrahedron2010, 66, 8441. (h) Klásek, A.; Křemen, F.; Křemenová, H.; Lyčka, A.; Rouchal, M. Tetrahedron2017, 73, 1583. (i) Klásek, A.; Lyčka, A.; Holčapek, M.; Kovář, M.; Hoza, I. J. Heterocycl. Chem. 2006, 43, 1251.
Shin, Y. S.; Song, S. J. Kang, S. U.; Hwang, H. S.; Choi, J. W.; Lee, B. H.; Jung, Y.-S.; Kim, C.-H. Neurosciences2013, 232, 1.
Cifuentes-Pagano, M. E.; Meijles, D. N.; Pagano, P. J. Curr. Pharm. Design2015, 21, 6023.
Mittal, R.; Debs, L. H.; Nguyen, D.; Patel, A. P.; Grati, M.; Mittal, J.;Yan, D.; Eshraghi, A. A.; Liu, X. Z. J. Cell. Physiol.2017, 232, 2710.
Marckwald, W. Ber. Dtsh. Chem. Ges.1892, 25, 2354.
Borduas, N.; Place, B.; Wentworth, G. R. F.; Abbatt, P. D.; Murphy, J. G. Atmos. Chem. Phys.2016, 16, 703.
Ermans, A.-M.; Bourdoux, P. In Environmental Goitrogenesis; Gaitan, E., Ed.; CRC Press: Boca Raton, 1989, p. 15.
Chiang, Y.; Kresge, A. J. Can. J. Chem.2000, 78, 1627.
Berger, S.; Braun, S. 200 and More NMR Experiments: A Practical Course; Wiley-VCH: Weinheim, 2004, 3rd ed.
Claridge, T. D. W. High-Resolution NMR Techniques in Organic Chemistry; Elsevier: Amsterdam, 2016, 3rd ed.
Marek, R.; Lyčka, A.; Kolehmainen, E.; Sievanen, E.; Toušek, J. Curr. Org. Chem.2007, 11, 1154.
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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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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DOI: https://doi.org/10.1007/s10593-020-02701-9