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Статья
2021

Synthesis and Structure of (2E)-3-Aryl(hetaryl)-2-[5-bromo-4-aryl(hetaryl)-1,3-thiazol-2-yl]acrylonitriles


N. A. PakholkaN. A. Pakholka, V. L. AbramenkoV. L. Abramenko, V. V. DotsenkoV. V. Dotsenko, N. A. AksenovN. A. Aksenov, I. V. AksenovaI. V. Aksenova, S. G. KrivokolyskoS. G. Krivokolysko
Российский журнал общей химии
https://doi.org/10.1134/S1070363221030038
Abstract / Full Text

Bromination of (2E)-3-aryl(hetaryl)-2-[4-aryl(hetaryl)-1,3-thiazol-2-yl]acrylonitriles proceeds regioselectively at the C5 atom of the thiazole ring with the formation of new (2E)-3-aryl(hetaryl)-2-[5-bromo-4-aryl(hetaryl)-1,3-thiazol-2-yl]acrylonitriles. The latter were alternatively obtained by the reaction of aldehydes, cyanothioacetamide, α-bromoketones and bromine in the presence of triethylamine in DMF. Structure of the key compounds was confirmed using 2D NMR spectroscopy and single crystal X-ray diffraction analysis.

Author information
  • Laboratory ChemEx, V. Dal Lugansk State University, 91034, Lugansk, UkraineN. A. Pakholka, V. L. Abramenko & S. G. Krivokolysko
  • Kuban State University, 350040, Krasnodar, RussiaV. V. Dotsenko
  • North Caucasus Federal University, 355009, Stavropol, RussiaV. V. Dotsenko, N. A. Aksenov & I. V. Aksenova
  • St. Luke Lugansk State Medical University, 91045, Lugansk, UkraineS. G. Krivokolysko
References
  1. Paladhi, S., Jana, B., Pathak, S., and Mannab, S.K., Arkivoc, 2019, p. 256. https://doi.org/10.24820/ark.5550190.p010.911
  2. Alneyadi, S.S., Heterocycles, 2018, vol. 96, no. 5, p. 803. https://doi.org/10.3987/REV-17-878
  3. Metwally, M.A., Farahat, A.A., and Abdel-Wahab, B.F., J. Sulfur Chem., 2010, vol. 31, no. 4, p. 315. https://doi.org/10.1080/17415993.2010.482155
  4. Song, Y.X. and Du, D.M., Org. Biomol. Chem., 2020, vol. 18, no. 31, p. 6018. https://doi.org/10.1039/D0OB01261K
  5. Rouf, A. and Tanyeli, C., Eur. J. Med. Chem., 2015, vol. 97, p. 911. https://doi.org/10.1016/j.ejmech.2014.10.058
  6. Tawfik, S.S., Liu, M., and Farahat, A.A., Arkivoc, 2020, p. 180. https://doi.org/10.24820/ark.5550190.p011.308
  7. Chhabria, M.T., Patel, S., Modi, P., and Brahmkshatriya, P.S., Curr. Top. Med. Chem., 2016, vol. 16, no. 26, p. 2841. https://doi.org/10.2174/1568026616666160506130731
  8. Ali, S.H. and Sayed, A.R., Synth. Commun., 2020. https://doi.org/10.1080/00397911.2020.1854787
  9. de Souza, M.V.N., J. Sulfur Chem., 2005, vol. 26, nos. 4– 5, p. 429. https://doi.org/10.1080/17415990500322792
  10. Mishra, R., Sharma, P.K., Verma, P.K., Tomer, I., Mathur, G., and Dhakad, P.K., J. Heterocycl. Chem., 2017, vol. 54, no. 4, p. 2103. https://doi.org/10.1002/jhet.2827
  11. Zhong, J., Nat. Prod. Rep., 2013, vol. 30, p. 869. https://doi.org/10.1039/c3np70006b
  12. Sundeep, K.M., Ramandeep, K., Rohit, B., Kapil, K., Virender, S., Ravi, S., Rupinder, K., and Ravindra, K.R., Bioorg. Chem., 2017, vol. 75, p. 406. https://doi.org/10.1016/j.bioorg.2017.10.014
  13. Hui-Zhen, Z., Lin-Ling, G., Hui, W., and Cheng-He, Z., Mini Rev. Med. Chem., 2017, vol. 17, no. 2, p. 122. https://doi.org/10.2174/1389557516666160630120725
  14. Preeti, A., Rakesh, N., Surendra, K.N., Sachin, K.S., and Vikramjeet, J., Med. Chem. Res., 2016, vol. 25, p. 1717. https://doi.org/10.1007/s00044-016-1610-2
  15. Dyachenko, V.D., Dyachenko, I.V., and Nenajdenko, V.G., Russ. Chem. Rev., 2018, vol. 87, no. 1, p. 1. https://doi.org/10.1070/RCR4760
  16. Mageramov, A.M., Shykhalyev, N.G., Dyachenko, V.D., Dyachenko, I.V., and Nenaidenko, V.G., α-Tsyanotioatsetamid (α-Cyanothioacetamide), Moscow: Tekhnosfera, 2018.
  17. Abd El-Gilil, Sh.M., J. Mol. Struct., 2019, vol. 1194, p. 144. https://doi.org/10.1016/j.molstruc.2019.04.048
  18. Suntsova, P.O., Eltyshev, A.K., Pospelova, T.A., Slepukhin, P.A., Benassi, E., and Belskaya, N.P., Dyes Pigm., 2019, vol. 166, p. 60. https://doi.org/10.1016/j.dyepig.2019.02.051
  19. Bashandy, M.S. and Abd El-Gilil, Sh.M., Heterocycles, 2016, vol. 92, no. 3, p. 431. https://doi.org/10.3987/COM-15-13384
  20. Hussain, S.M., El-Reedy, A.M., and El-Sharabasy, S.A., Tetrahedron, 1988, vol. 44, no. 1, p. 241. https://doi.org/10.1016/S0040-4020(01)85113-9
  21. Dyachenko, V.D. and Litvinov, V.P., Chem. Heterocycl. Compd., 1998, vol. 34, no. 2, p. 188. https://doi.org/10.1007/BF02315182
  22. Krivokolysko, S.G., Dyachenko, V.D., Nesterov, V.N., and Litvinov, V.P., Chem. Heterocycl. Compd., 2001, vol. 37, no. 2, p. 855. https://doi.org/10.1023/A:1012499424379
  23. Dyachenko, V.D. and Litvinov, V.P., Russ. J. Org. Chem., 1998, vol. 34, no. 4, p. 557.
  24. Dyachenko, V.D., Kashner, A.Yu., and Samusenko, Yu.V., Russ. J. Gen. Chem., 2014, vol. 84, no. 2, p. 259. https://doi.org/10.1134/S1070363214020169
  25. Goncharenko, M.P., Sharanin, Yu.A., and Turov, A.V., Russ. J. Org. Chem., 1993, vol. 29, no. 8, p. 1341.
  26. Nesterov, V.N., Montoya, N.G., Antipin, M.Yu., Sanghadasa, M., Clark, R.D., and Timofeeva, T.V., Acta Crystallogr. (С), 2002, vol. 58, p. o72. https://doi.org/10.1107/S0108270101020170
  27. Khafagy, M.M., El-Maghraby, A.A., Hassan, S.M., and Bashandy, M.S., Phosphorus, Sulfur, Silicon, Relat. Elem., 2004, vol. 179, p. 2113. https://doi.org/10.1080/10426500490475049
  28. Hassan, S.M., Abdel Aal, M.M., El-Maghraby, A.A., and Bashandy, M.S., Phosphorus, Sulfur, Silicon, Relat. Elem., 2009, vol. 184, p. 427. https://doi.org/10.1080/10426500802176523
  29. Dyachenko, V.D., Russ. J. Gen. Chem., 2015, vol. 85, no. 4, p. 861. https://doi.org/10.1134/S1070363215040167
  30. Krivokolysko, S.G., Dyachenko, V.D., and Litvinov, V.P., Chem. Heterocycl. Compd., 1999, vol. 35, no. 10, p. 1190. https://doi.org/10.1007/BF02323378
  31. Dyachenko, I.V., Ramazanova, E.Yu., and Dyachenko, V.D., Russ. J. Org. Chem., 2014, vol. 50, no. 12, p. 1821. https://doi.org/10.1134/S1070428014120185
  32. Dyachenko, V.D., Chernega, A.N., and Garasevich, S.G., Russ. J. Gen. Chem., 2005, vol. 75, no. 10, p. 1610. https://doi.org/10.1007/s11176-005-0475-8
  33. Dyachenko, V.D., Russ. J. Org. Chem., 2014, vol. 42, no. 5, p. 724. https://doi.org/10.1134/S1070428006050137
  34. Dyachenko, V.D., Rylʹskaya, T.A., and Savchuk, S.V., Visn. Kharkiv. Nats. Univ., 2006, vol. 731, no. 14(37), p. 86.
  35. Ahmed, A.A.M., Mekky, A.E.M., Elwahy, A.H.M., and Sanad, S.M.H., Synth. Commun., 2020, vol. 50, no. 6, p. 796. https://doi.org/10.1080/00397911.2019.1689269
  36. Abdelhamid, A.O., Zohdi, H.F., and Rateb, N.M., J. Chem. Res. (S), 1995, p. 144.
  37. Abdelhamid, A.O., Zohdi, H.F., Rateb, N.M., and Abdelhamid, A.O., Phosphorus, Sulfur, Silicon, Relat. Elem., 1998, vol. 133, no. 1, p. 103. https://doi.org/10.1080/10426509808032458
  38. Abdelbamid, A.O. and Al-Shehri, S.M., J. Chem. Res. Miniprint, 1997, no. 7, p. 1681.
  39. Sharanin, Yu.A., Shestopalov, A.M., Promonenkov, V.K., and Rodinovskaya, L.A., J. Org. Chem. USSR, 1984, vol. 20, no. 7, p. 1402.
  40. Schäfer, V.H. and Gewald, K., J. Prakt. Chem., 1974, vol. 316, no. 4, p. 684. https://doi.org/10.1002/prac.19743160421
  41. Dyachenko, I.V., Dyachenko, V.D., Dorovatovskii, P.V., Khrustalev, V.N., and Nenaidenko, V.G., Russ. J. Org. Chem., 2019, vol. 55, no. 2, p. 215. https://doi.org/10.1134/S1070428019020131
  42. Smith, C.D., French, K.J., and Yun, J.K., US Patent 2004/0034075 A1, 2004.
  43. Smith, C.D., French, K.J., and Yun, J.K., WO Patent 03/105840 A2, 2003, USA.
  44. Gambacorti Passerini, C., Gunby, R.H., Zambon, A., Scapozza, L., Ahmed, S., Goekjian, P.G., Gueyrard, D., Popowycz, F., and Schneider, C., EP Patent 2 107 054 A1, 2009.
  45. Gambacorti Passerini, C., Gunby, R.H., Zambon, A., Scapozza, L., Ahmed, S., Goekjian, P.G., Gueyrard, D., Popowycz, F., and Schneider, C., WO Patent 2009/121535 A2, 2009, USA.
  46. Brunskill, J.S.A., De, A., and Ewing, D.F., J. Chem. Soc. Perkin Trans. 1, 1978, no. 6, p. 629. https://doi.org/10.1039/P19780000629
  47. Dotsenko, V.V., Krivokolysko, S.G., Polovinko, V.V., and Litvinov, V.P., Chem. Heterocycl. Compd., 2012, vol. 48, p. 309. https://doi.org/10.1007/s10593-012-0991-5
  48. Dolomanov, O.V., Bourhis, L.J., Gildea, R.J., Howard, J.A.K., and Puschmann, H., J. Appl. Cryst., 2009, vol. 42, p. 339. https://doi.org/10.1107/S0021889808042726
  49. Sheldrick, G.M., Acta Crystallogr. (A), 2008, vol. 64, p. 112. https://doi.org/10.1107/S0108767307043930
  50. Sheldrick, G.M., Acta Crystallogr. (C), 2015, vol. 71, p. 3. https://doi.org/10.1107/S2053229614024218