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Synthesis of Novel Carbofunctional Organosilicon Sulfanyl Derivatives of Benzazoles and Triazoles

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Abstract

Previously unknown carbofunctional organosilicon derivatives of azoles are synthesized by the reactions of sulfanyl derivatives of benzoxazole, benzothiazole, benzimidazole, and triazole with (iodomethyl)dimethyl(phenyl)silane and (iodomethyl)(ethynyl)dimethylsilane.

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REFERENCES

  1. Finšgar, M. and Merl, D.K., Corros. Sci., 2014, vol. 83, p. 164. https://doi.org/10.1016/j.corsci.2014.02.016

    Article  CAS  Google Scholar 

  2. Finšgar, M., Corros. Sci., 2013, vol. 72, p. 90. https://doi.org/10.1016/j.corsci.2013.03.010

    Article  CAS  Google Scholar 

  3. Izquierdo, J., Santana, J.J., González, S., and Souto, R.M., Prog. Org. Coat., 2012, vol. 74, p. 526. https://doi.org/10.1016/j.porgcoat.2012.01.019

    Article  CAS  Google Scholar 

  4. More, A.P. and Mhaske, Sh.T., Arabian J. Sci. Eng., 2016, vol. 41, p. 2239. https://doi.org/10.1007/s13369-015-1974-5

    Article  CAS  Google Scholar 

  5. Hazazi, O.A., Fawzy, A., Shaaban, M.R., and Awad, M.I., Int. J. Electrochem. Sci., 2014, vol. 9, p. 1378.

    Google Scholar 

  6. Refaey, S.A.M., Taha, F., and Abd El-Malak, A.M., Appl. Surf. Sci., 2004, vol. 236, p. 175. https://doi.org/10.1016/j.apsusc.2004.04.016

    Article  CAS  Google Scholar 

  7. Buckley, A.N., Hope, G.A., Parker, G.K., Steyn, J., and Woods, R., Miner. Eng., 2017, vol. 109, p. 80. https://doi.org/10.1016/j.mineng.2017.03.0020892-6875

    Article  CAS  Google Scholar 

  8. Contini, G., Castro, V.D., Polzonetti, G., Comelli, G., Brena, B., and Marabini, A.M., Surf. Sci., 1997, vol. 391, p. 65. https://doi.org/10.1016/S0039-6028(97)00455-X

    Article  CAS  Google Scholar 

  9. Finšgar, M. and Merl, D.K., Corros. Sci., 2014, vol. 80, p. 82. https://doi.org/10.1016/j.corsci.2013.11.022

    Article  CAS  Google Scholar 

  10. Ilichev, V.A., Silantyeva, L.I., Yablonskiy, A.N., Andreev, B.A., Rumyantcev, R.V., Fukina, G.K., and Bochkarev, M.N., Dalton Trans., 2019, vol. 48, p. 1060. https://doi.org/10.1039/c8dt04601h

    Article  CAS  PubMed  Google Scholar 

  11. Ilichev, V.A., Blinova, L.I., Rozhkov, A.V., Balashova, T.V., Rumyantcev, R.V., Fukin, G.K., and Bochkarev, M.N., Molecul. Structure J., 2017, vol. 1148, p. 201. https://doi.org/10.1016/j.molstruc.2017.07.035

    Article  CAS  Google Scholar 

  12. Kazemi, E., Dadfarnia, Sh., Shabani, A.M.H., and Hashemi, P.S., Int. J. Environ. Anal. Chem., 2017, vol. 97, p. 743. https://doi.org/10.1080/03067319.2017.1353087

    Article  CAS  Google Scholar 

  13. Dahaghin, Z., Mousavi, H.Z., and Sajjadi, S.M., J. Mol. Liq., 2017, vol. 231, p. 386. https://doi.org/10.1016/j.molliq.2017.02.023

    Article  CAS  Google Scholar 

  14. Wu, F.-L., Hussein, W.M., Ross, B.P., and McGeary, R.P., Current Org. Chem., 2012, vol. 16, p. 1555. https://doi.org/10.2174/138527212800840964

    Article  CAS  Google Scholar 

  15. Horst, M.V.D., Hendrikse, K.G., and Woolard, C.D., J. Appl. Polym. Sci., 2003, vol. 89, p. 47. https://doi.org/10.1002/app.11869

    Article  CAS  Google Scholar 

  16. Cano, N.H., Ballari, M.S., López, A.G., and Santiago, A.N., J. Agric. Food Chem., 2015, vol. 63, p. 3681. https://doi.org/10.1021/acs.jafc.5b00150

    Article  CAS  Google Scholar 

  17. Azam, M.A. and Suresh, B., Sci Pharm., 2012, vol. 80, p. 789. https://doi.org/10.3797/scipharm.1204-27

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  18. Ahmed, M.R. and Mohsin, A.A., Iraqi J. Sci., 2015, vol. 56, p. 303.

    Google Scholar 

  19. Haider, S., Alam, M.S., Hamid, H., Shafi, S., Dhulap, A., Hussain, F., Alam, P., Umar, S., Pasha, M.A.Q., Bano, S., Nazreen, S., Ali, Y., and Kharbanda, C., Eur. J. Med. Chem., 2014, vol. 81, p. 204. https://doi.org/10.1016/j.ejmech.2014.05.012

    Article  CAS  PubMed  Google Scholar 

  20. Gupta, S., Gupta, S.P., Upmanyu, N., and Garg, G., J.Drug Des. Med. Chem., 2015, vol. 1, p. 12. https://doi.org/10.11648/j.jddmc.20150102.11

    Article  Google Scholar 

  21. De Almeida, M.V., Cardoso, S.H., De Assis, J.V., and De Souza, M.V.N., J. Sulfur Chem., 2007, vol. 28, p. 17. https://doi.org/10.1080/17415990601055291

    Article  CAS  Google Scholar 

  22. Holla, B.S., Veerendra, B., Shivananda, M.K., and Poojary, B., Eur. J. Med. Chem., 2003, vol. 38, p. 759. https://doi.org/10.1016/s0223-5234(03)00128-4

    Article  Google Scholar 

  23. Siwek, A., Wujec, M., Dobosz, M., Jagiełło-Wójtowicz, E., Chodkowska, A., Kleinrok, A., and Paneth, P., Cent. Eur. J. Chem., 2008, vol. 6, p. 47. https://doi.org/10.2478/s11532-007-0058-0

    Article  CAS  Google Scholar 

  24. Wujec, M., Pitucha, M., Dobosz, M., Kosikowska, U., and Malm, A., Acta Pharm., 2004, vol. 54, p. 251.

    CAS  PubMed  Google Scholar 

  25. Demirbas, N., Karaoglu, S.A., Demirbas, A., and Sancak, K., Eur. J. Med. Chem., 2004, vol. 39, p. 793. https://doi.org/10.1016/j.ejmech.2004.06.007

    Article  CAS  PubMed  Google Scholar 

  26. Silicon in Organic, Organometallic, and Polymer Chemistry, Brook, M.A., Eds., New York: J. Wiley and Sons, 2000.

  27. Zdrahala, R.J. and Zdrahala, I.J., J. Biomater. Appl., 1999, vol. 14, p. 67. https://doi.org/10.1177/088532829901400104

    Article  CAS  PubMed  Google Scholar 

  28. Bernacca, G.M., Straub, I., and Wheatley, D.J., J. Biomat. Mater. Res., 2002, vol. 61, p. 138. https://doi.org/10.1002/jbm.10149

    Article  CAS  Google Scholar 

  29. Voronkov, M.G., Zelchan, G.I., and Lukevich, E.R., Kremnii i zhizn’ (Silicon and Life), Riga: Zinatne, 1978.

  30. Voronkov, M.G., Trofimova, O.M., Bolgova, Y.I., and Chernov, N.F., Chem. Heterocycl. Compd., 2001, vol. 37, p. 1358. https://doi.org/10.1023/A:1017994916574

    Article  CAS  Google Scholar 

  31. Voronkov, M.G., Chernov, N.F., Trofimova, O.M., and Aksamentova, T.N., Russ. Chem. Bull., 1993, vol. 42, p. 1883. https://doi.org/10.1007/BF00699009

    Article  Google Scholar 

  32. Rubina, K., Abele, E., Arsenyan, P., Abele, R., Veveris, M., and Lukevics, E., Metal Based Drugs, 2001, vol. 8, p. 85. https://doi.org/10.1155/MBD.2001.85

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  33. Abele, E., Rubina, K., Abele, R., Dzenitis, O., Arsenyan, P., Popelis, J., Veveris, M., Meirena, D., and Lukevics, E., Metal Based Drugs, 2002, vol. 8, p. 307. https://doi.org/10.1155/MBD.2002.307

    Article  PubMed  PubMed Central  Google Scholar 

  34. Abele, R., Abele, E., Rubina, K., Dzenitis, O., Arsenyan, P., Shestakova, I., Nesterova, A., Domracheva, I., Popelis, J., Grinberga, S., and Lukevics, E., Chem. Heterocycl. Comp., 2002, vol. 38, p. 867. https://doi.org/10.1023/A:1020650224525

    Article  CAS  Google Scholar 

  35. Grebneva, E.A., Bolgova, Yu.I., Trofimova, O.M., Albanov, A.I., and Borodina, T.N., Chem. Heterocycl. Comp., 2019, vol. 55, p. 762. https://doi.org/10.1007/s10593-019-02532-3

    Article  CAS  Google Scholar 

  36. Abele, E., Abele, R., Arsenyan, P., Belyakov, S., Veveris, M., and Lukevics, E., Chem. Heterocycl. Compd., 2007, vol. 43, p. 220. https://doi.org/10.1007/s10593-019-02532-310.1007/s10593-007-0034-9

    Article  CAS  Google Scholar 

  37. Zhilitskaya, L.V., Yarosh, N.O., Shagun, L.G., Dorofeev, I.A., and Larina, L.I., Mendeleev Commun., 2017, vol. 27, p. 352. https://doi.org/10.1016/j.mencom.2017.07.010

    Article  CAS  Google Scholar 

  38. Zhilitskaya, L.V., Yarosh, N.O., Shagun, L.G., and Dorofeev, I.A., Russ. J. Gen. Chem., 2019, vol. 89, p. 1625. https://doi.org/10.1134/S1070363219080127

    Article  CAS  Google Scholar 

  39. Yarosh, N.O., Zhilitskaya, L.V., Shagun, L.G., Dorofeev, I.A., and Larina, L.I., Russ. J. Org. Chem., 2019, vol. 55, p. 1071. https://doi.org/10.1134/S0514749219080019

    Article  CAS  Google Scholar 

  40. Yarosh, N.O., Zhilitskaya, L.V., Shagun, L.G., Dorofeev, I.A., and Larina, L.I., Russ. J. Org. Chem., 2017, vol. 53, p. 413. https://doi.org/10.1134/S1070428017030162

    Article  CAS  Google Scholar 

  41. Foreman, K.W., Nguyen, H.N., Ofori, L.O., Wanner, J., and Werner, D., WO Patent Appl. no. WO 2016/183359.

  42. http://www.pharmaexpert.ru/PASSOnline/

  43. Lee, T.R. and Kim, K., J. Heterocycl. Chem., 1989, vol. 26, p. 747. https://doi.org/10.1002/jhet.5570260344

    Article  CAS  Google Scholar 

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ACKNOWLEDGMENTS

The work was performed using the equipment of the Baikal Analytical Center for Collective Use, Siberian Branch, Russian Academy of Sciences.

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Correspondence to L. V. Zhilitskaya.

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Yarosh, N.O., Zhilitskaya, L.V., Shagun, L.G. et al. Synthesis of Novel Carbofunctional Organosilicon Sulfanyl Derivatives of Benzazoles and Triazoles. Russ J Org Chem 56, 833–839 (2020). https://doi.org/10.1134/S1070428020050164

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  • DOI: https://doi.org/10.1134/S1070428020050164

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