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Synthesis of Functionalized 2,3-Dihydro-5H-[1,3]thiazolo[2,3-b]quinazolin-5-one via Intramolecular Electrophilic Cyclization

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Abstract

3-(2-Methylprop-2-en-1-yl)-2-sulfanylidene-7-(trifluoromethyl)-2,3-dihydroquinazolin-4(1H)-one reacted with halogens (bromine and iodine), chalcogen tetrahalides, and p-methoxyphenyltellurium trichloride in a regioselective manner to give linearly fused 2-halomethyl-2-methyl-5-oxo-8-(trifluoromethyl)-2,3-dihydro-5H-[1,3]thiazolo[2,3-b]quinazolinium trihalides, 2-methyl-5-oxo-2-[(trihalo-λ4-chalcogenyl)methyl]-8-(trifluoromethyl)-2,3-dihydro-5H-[1,3]thiazolo[2,3-b]quinazolinium halides, and 2-{[dichloro(4-methoxyphenyl)-λ4-tellanyl]methyl}-8-(trifluoromethyl)-2,3-dihydro-5H-[1,3]thiazolo[2,3-b]quinazolin-5-one, respectively.

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REFERENCES

  1. Wan, Z., Hu, D., Li, P., Xie, D., and Gan, X., Molecules, 2015, vol. 20, p. 11861. https://doi.org/10.3390/molecules200711861

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  2. Long, C., Li, P., Chen, M., Dong, L., Hu, D., and Song, B., Eur. J. Med. Chem., 2015, vol. 102, p. 639. https://doi.org/10.1016/j.ejmech.2015.08.029

    Article  CAS  PubMed  Google Scholar 

  3. Pati, B. and Banerjee, S., J. Adv. Pharm. Educ. Res., 2013, vol. 3, p. 136.

    CAS  Google Scholar 

  4. Ighachane, H., Sedra, M.H., and Lazrek, H.B., J. Mater. Environ. Sci., 2017, vol. 8, p. 134.

    CAS  Google Scholar 

  5. Rahman, M.U., Jeyabalan, G., Saraswat, P., Parveen, G., Khan, S., and Yar, M.S., Synth. Commun., 2017, vol. 47, p. 379. https://doi.org/10.1080/00397911.2016.1269926

    Article  CAS  Google Scholar 

  6. Xie, D., Shi, J., Zhang, A., Lei, Z., Zu, G., Fu, Y., Gan, X., Yin, L., Song, B., and Hu, D., Bioorg. Chem., 2018, vol. 80, p. 433. https://doi.org/10.1016/j.bioorg.2018.06.026

    Article  CAS  PubMed  Google Scholar 

  7. Bilyi, A.K., Antypenko, L.M., Ivchuk, V.V., Kamyshnyi, O.M., Polishchuk, N.M., and Kovalenko, S.I., ChemPlusChem, 2015, vol. 80, p. 950. https://doi.org/10.1002/cplu.201500051

    Article  CAS  Google Scholar 

  8. Antypenko, L., Kovalenko, S.I., Posylkina, Y., Nikitin, V., Fedyunina, N., and Ivchuk, V., J. Enzyme Inhib. Med. Chem., 2016, vol. 31, p. 253. https://doi.org/10.3109/14756366.2015.1018243

    Article  CAS  PubMed  Google Scholar 

  9. Palanki, M.S.S., Erdman, P.E., Ren, M., Suto, M., Bennett, B.L., Manning, A., Ransone, L., Spooner, C., Desai, S., Ow, A., Totsuka, R., Tsao, P., and Toriumi, W., Bioorg. Med. Chem. Lett., 2003, vol. 13, p. 4077. https://doi.org/10.1016/j.bmcl.2003.08.047

    Article  CAS  PubMed  Google Scholar 

  10. Tobe, M., Isobe, Y., Tomizawa, H., Nagasaki, T., Obara, F., and Hayashi, H., Bioorg. Med. Chem., 2003, vol. 11, p. 609. https://doi.org/10.1016/S0968-0896(02)00338-3

    Article  CAS  PubMed  Google Scholar 

  11. Wang, W., Zhao, X., Li, T., Tian, Q., Chen, L., Zhou, Z., Li, Z., Wang, X., Rong, Y., Jiang, L., Liu, Y., and Sun, J., US Patent Appl. Pub. no. 20160168129A1, 2016.

  12. Casuscelli, F., Piutti, C., Ermoli, A., and Faiardi, D., US Patent Appl. Pub. no. 20120190678A1, 2012.

  13. Hartwig, J. and Fier, P., WO Patent Appl. Pub. no. 2015013715A2, 2015.

  14. Ravez, S., Castillo-Aguilera, O., Depreux, P., and Goossens, L., Expert Opin. Ther. Pat., 2015, vol. 25, p. 789. https://doi.org/10.1517/13543776.2015.1039512

    Article  CAS  PubMed  Google Scholar 

  15. Slivchuk, S.V., Brovarets, V.S., and Drach, B.S., Russ. J. Gen. Chem., 2008, vol. 78, p. 1210. https://doi.org/10.1134/S1070363208060194

    Article  CAS  Google Scholar 

  16. Slivka, N.Yu., Gevaza, Yu.I., and Staninets, V.I., Chem. Heterocycl. Compd., 2004, vol. 40, p. 660. https://doi.org/10.1023/B:COHC.0000037323.22839.9f

    Article  CAS  Google Scholar 

  17. Frolova, T.V., Slepuhin, P.A., and Kim, D.G., Chem. Heterocycl. Compd., 2011, vol. 47, p. 252. https://doi.org/10.1007/s10593-011-0751-y

    Article  CAS  Google Scholar 

  18. Studzińska, R., Wróblewski, M., KarczmarskaWódzka, A., and Kołodziejska, R., Tetrahedron Lett., 2014, vol. 55, p. 1384. https://doi.org/10.1016/j.tetlet.2014.01.033

    Article  CAS  Google Scholar 

  19. Bakhteeva, E.I., Kim, D.G., Dmitriev, M.V., and Krylova, Y.E., Russ. J. Org. Chem., 2019, vol. 55, p. 748. https://doi.org/10.1134/S0514749219060028

    Article  CAS  Google Scholar 

  20. Zborovskii, Yu.L., Orysyk, V.V., Dobosh, A.A., Staninets, V.I., Pirozhenko, V.V., and Chernega, A.N., Chem. Heterocycl. Compd., 2003, vol. 39, p. 1099. https://doi.org/10.1023/B:COHC.0000003532.58469.cc

    Article  CAS  Google Scholar 

  21. Orysyk, V.V., Zborovskii, Yu.L., Staninets, V.I., Dobosh, A.A., and Khripak, S.M., Chem. Heterocycl. Compd., 2003, vol. 39, p. 640. https://doi.org/10.1023/A:1025154317771

    Article  CAS  Google Scholar 

  22. Wippich, P., Gütschow, M., and Leistner, S., Synthesis, 2000, vol. 2000, no. 5, p. 714. https://doi.org/10.1055/s-2000-6390

    Article  Google Scholar 

  23. Vas’kevich, R.I., Khripak, S.M., Staninets, V.I., Zborovskii, Yu.L., and Chernega, A.N., Russ. J. Org. Chem., 2000, vol. 36, p. 1061.

    Google Scholar 

  24. Vaskevich, R.I., Khripak, S.M., Staninets, V.I., Zborovskij, Y.L., Nesterenko, A.M., and Pirozhenko, V.V., Ukr. Khim. Zh., 2000, vol. 66, p. 47.

    CAS  Google Scholar 

  25. Vas’kevich, A.I., Vas’kevich, R.I., Staninets, V.I., But, S.A., and Chernega, A.N., Russ. J. Org. Chem., 2007, vol. 43, p. 1526. https://doi.org/10.1134/S107042800710020X

    Article  CAS  Google Scholar 

  26. Slivka, M., Krivovjaz, A., Slivka, M., and Lendel, V., Heterocycl. Commun., 2013, vol. 19, p. 189. https://doi.org/10.1515/hc-2013-0036

    Article  CAS  Google Scholar 

  27. Bentya, A.V., Vas’kevich, R.I., Bol’but, A.V., Vovk, M.V., Staninets, V.I., Turov, A.V., and Rusanov, E.B., Russ. J. Org. Chem., 2008, vol. 44, p. 1362. https://doi.org/10.1134/S1070428008090194

    Article  CAS  Google Scholar 

  28. Vas’kevich, R.I., Bentya, A.V., Turov, A.V., Rusanov, E.B., Staninets, V.I., and Vovk, M.V., Russ. J. Org. Chem., 2012, vol. 48, p. 713. https://doi.org/10.1134/S1070428012050144

    Article  Google Scholar 

  29. Svaljavyn, O.V., Onysko, M.Y., Turov, A.V., Vlasenko, Y.G., and Lendel, V.G., Chem. Heterocycl. Compd., 2013, vol. 49, p. 491. https://doi.org/10.1007/s10593-013-1273-6

    Article  CAS  Google Scholar 

  30. Onysko, M.Yu., Svalyavin, O.V., Turov, A.V., and Lendel, V.G., Chem. Heterocycl. Compd., 2008, vol. 44, p. 872. https://doi.org/10.1007/s10593-008-0123-4

    Article  CAS  Google Scholar 

  31. Onisko, M.Yu., Svalyavin, O.V., and Lendel, V.G., Chem. Heterocycl. Compd., 2007, vol. 43, p. 496. https://doi.org/10.1007/s10593-007-0072-3

    Article  CAS  Google Scholar 

  32. Vas’kevich, R.I., Dyachenko, I.V., Vas’kevich, A.I., Rusanov, E.B., and Vovk, M.V., Russ. J. Org. Chem., 2015, vol. 51, p. 556. https://doi.org/10.1134/S1070428015040168

    Article  CAS  Google Scholar 

  33. Dyachenko, I.V., Vas’kevich, R.I., and Vovk, M.V., Russ. J. Org. Chem., 2014, vol. 50, p. 263. https://doi.org/10.1134/S1070428014020201

    Article  CAS  Google Scholar 

  34. Dyachenko, I.V., Vas’kevich, R.I., Vas’kevich, A.I., Polovinko, V.V., and Vovk, M.V., Russ. J. Org. Chem., 2018, vol. 54, p. 436. https://doi.org/10.1134/S1070428018030119

    Article  CAS  Google Scholar 

  35. Potapov, V.A., Khabibulina, A.G., Udalova, S.I., Musalov, M.V., Musalova, M.V., Shkurchenko, I.V., Albanov, A.I., and Amosova, S.V., Russ. J. Gen. Chem., 2019, vol. 89, p. 1931. https://doi.org/10.1134/S1070363219090317

    Article  CAS  Google Scholar 

  36. Musalova, M.V., Ivanova, L.A., Musalov, M.V., Potapov, V.A., Zinchenko, S.V., and Amosova, S.V., Russ. J. Org. Chem., 2018, vol. 54, p. 1725. https://doi.org/10.1134/S1070428018110179

    Article  CAS  Google Scholar 

  37. Musalov, M.V., Kurkutov, E.O., Potapov, V.A., Khabibulina, A.G., Albanov, A.I., and Amosova, S.V., Russ. J. Org. Chem., 2017, vol. 53, p. 1809. https://doi.org/10.1134/S1070428017120041

    Article  CAS  Google Scholar 

  38. Amosova, S.V., Shagun, V.A., Martynov, A.V., Makhaeva, N.A., Larina, L.I., Lysenko, K.A., and Voronkov, M.G., J. Organomet. Chem., 2007, vol. 692, p. 3307. https://doi.org/10.1016/j.jorganchem.2007.01.023

    Article  CAS  Google Scholar 

  39. Amosova, S.V., Martynov, A.V., Penzik, M.V., Makhaeva, N.A., Potapov, V.A., Albanov, A.I., Zhilitskaya, L.V., and Voronkov, M.G., J. Organomet. Chem., 2008, vol. 693, p. 3650. https://doi.org/10.1016/j.jorganchem.2008.05.037

    Article  CAS  Google Scholar 

  40. Amosova, S.V., Penzik, M.V., Martynov, A.V., Makhaeva, N.A., Yarosh, N.O., and Voronkov, M.G., J. Organomet. Chem., 2008, vol. 693, p. 3346. https://doi.org/10.1016/j.jorganchem.2008.07.008

    Article  CAS  Google Scholar 

  41. Onis’ko, M.Yu., Lendel, V.G., and Staninets’, V.I., Ukr. Khim. Zh., 1999, vol. 65, p. 116.

    Google Scholar 

  42. Lendel, V.G., Pak, B.I., Balog, I.M., Kiyak, M.V., and Migalina, Yu.M., Chem. Heterocycl. Compd., 1990, vol. 26, p. 108. https://doi.org/10.1007/BF00506860

    Article  Google Scholar 

  43. Khripak, S.M., Yakubets, V.I., Lendel, V.G., Vas’kevich, R.I., and Staninets, V.I., Ukr. Khim. Zh., 1998, vol. 64, p. 128.

    CAS  Google Scholar 

  44. Migalina, Yu.V., Lendel, V.G., Balog, I.M., and Staninets, V.I., Ukr. Khim. Zh., 1981, vol. 47, p. 1293.

    CAS  Google Scholar 

  45. Migalina, Yu.V., Staninets, V.I., Lendel, V.G., Balog, I.M., Palyulin, V.A., Koz’min, A.S., and Zefirov, N.S., Chem. Heterocycl. Compd., 1977, vol. 13, p. 49. https://doi.org/10.1007/BF00479868

    Article  Google Scholar 

  46. Migalina, Yu.V., Sani, A.Yu., Balog, I.M., Petrus, V.V., Ershova, I.I., and Lendel, V.G., Chem. Heterocycl. Compd., 1989, vol. 25, p. 610. https://doi.org/10.1007/BF00470015

    Article  Google Scholar 

  47. Maluf, S.E., Melo, P.M.S., Varotti, F.P., Gazarini, M.L., Cunha, R.L.O.R., and Carmona, A.K., Parasitol. Int., 2016, vol. 65, p. 20. https://doi.org/10.1016/j.parint.2015.09.006

    Article  CAS  Google Scholar 

  48. dos Grecco, S.S., Reimão, J.Q., Tempone, A.G., Sartorelli, P., Cunha, R.L.O.R., Romoff, P., Ferreira, M.J.P., Fávero, O.A., and Lago, J.H.G., Exp. Parasitol., 2012, vol. 130, p. 141. https://doi.org/10.1016/j.exppara.2011.11.002

    Article  CAS  Google Scholar 

  49. Pimentel, I.A.S., de Siqueira Paladi, C., Katz, S., de Souza Júdice, W.A., Cunha, R.L.O.R., and Barbiéri, C.L., PLoS One, 2012, vol. 7, article no. e48780. https://doi.org/10.1371/journal.pone.0048780

  50. Caracelli, I., Maganhi, S.H., de Oliveira Cardoso, J., Cunha, R.L.O.R., Vega-Teijidoa, M.A., Zukerman-Schpector, J., and Tiekink, E.R.T., Z. Kristallogr., 2018, vol. 233, p. 113. https://doi.org/10.1515/zkri-2017-2079

    Article  CAS  Google Scholar 

  51. Silberman, A., Kalechman, Y., Hirsch, S., Erlich, Z., Sredni, B., and Albeck, A., ChemBioChem, 2016, vol. 17, p. 918. https://doi.org/10.1002/cbic.201500614

    Article  CAS  PubMed  Google Scholar 

  52. Cunha, R.L.O.R., Gouvea, I.E., and Juliano, L., An. Acad. Bras. Ciênc., 2009, vol. 81, p. 393. https://doi.org/10.1590/S0001-37652009000300006

    Article  CAS  PubMed  Google Scholar 

  53. Halpert, G. and Sredni, B., Autoimmun. Rev., 2014, vol. 13, p. 1230. https://doi.org/10.1016/j.autrev.2014.08.003

    Article  CAS  PubMed  Google Scholar 

  54. Abdel-Hafez, Sh.H., Russ. J. Bioorg. Chem., 2010, vol. 36, p. 370. https://doi.org/10.1134/S1068162010030131

    Article  CAS  Google Scholar 

  55. Pesarico, A.P., Sartori, G., dos Santos, C.F.A., Neto, J.S.S., Bortolotto, V., Santos, R.C.V., Nogueira, C.W., and Prigol, M., Microbiol. Res., 2013, vol. 168, p. 563. https://doi.org/10.1016/j.micres.2013.04.009

    Article  CAS  PubMed  Google Scholar 

  56. Libero, F.M., Xavier, M.C.D., Victoria, F.N., Nascente, P.S., Savegnago, L., Perin, G., and Alves, D., Tetrahedron Lett., 2012, vol. 53, p. 3091. https://doi.org/10.1016/j.tetlet.2012.04.040

    Article  CAS  Google Scholar 

  57. Kut, M., Fizer, M., Onysko, M., and Lendel, V., J. Heterocycl. Chem., 2018, vol. 55, p. 2284. https://doi.org/10.1002/jhet.3281

    Article  CAS  Google Scholar 

  58. Kut, M., Onysko, M., and Lendel, V., J. Heterocycl. Chem., 2018, vol. 55, p. 888. https://doi.org/10.1002/jhet.3114

    Article  CAS  Google Scholar 

  59. Kut, M., Onysko, M., and Lendel, V., Heterocycl. Commun., 2016, vol. 22, p. 347. https://doi.org/10.1515/hc-2016-0169

    Article  CAS  Google Scholar 

  60. Fizer, M., Synlett, 2013, vol. 24, p. 2019. https://doi.org/10.1055/s-0033-1339703

    Article  Google Scholar 

  61. Reichel, L. and Kirschbaum, E., Justus Liebigs Ann. Chem., 1936, vol. 523, p. 211. https://doi.org/10.1002/jlac.19365230113

    Article  CAS  Google Scholar 

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    N. M. Kut, M. Yu. Onysko & V. G. Lendel

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Kut, N.M., Onysko, M.Y. & Lendel, V.G. Synthesis of Functionalized 2,3-Dihydro-5H-[1,3]thiazolo[2,3-b]quinazolin-5-one via Intramolecular Electrophilic Cyclization. Russ J Org Chem 56, 1174–1180 (2020). https://doi.org/10.1134/S1070428020070088

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