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.
Similar content being viewed by others
REFERENCES
Finšgar, M. and Merl, D.K., Corros. Sci., 2014, vol. 83, p. 164. https://doi.org/10.1016/j.corsci.2014.02.016
Finšgar, M., Corros. Sci., 2013, vol. 72, p. 90. https://doi.org/10.1016/j.corsci.2013.03.010
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
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
Hazazi, O.A., Fawzy, A., Shaaban, M.R., and Awad, M.I., Int. J. Electrochem. Sci., 2014, vol. 9, p. 1378.
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
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
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
Finšgar, M. and Merl, D.K., Corros. Sci., 2014, vol. 80, p. 82. https://doi.org/10.1016/j.corsci.2013.11.022
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
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
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
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
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
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
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
Azam, M.A. and Suresh, B., Sci Pharm., 2012, vol. 80, p. 789. https://doi.org/10.3797/scipharm.1204-27
Ahmed, M.R. and Mohsin, A.A., Iraqi J. Sci., 2015, vol. 56, p. 303.
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
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
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
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
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
Wujec, M., Pitucha, M., Dobosz, M., Kosikowska, U., and Malm, A., Acta Pharm., 2004, vol. 54, p. 251.
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
Silicon in Organic, Organometallic, and Polymer Chemistry, Brook, M.A., Eds., New York: J. Wiley and Sons, 2000.
Zdrahala, R.J. and Zdrahala, I.J., J. Biomater. Appl., 1999, vol. 14, p. 67. https://doi.org/10.1177/088532829901400104
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
Voronkov, M.G., Zelchan, G.I., and Lukevich, E.R., Kremnii i zhizn’ (Silicon and Life), Riga: Zinatne, 1978.
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
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
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
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
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
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
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
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
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
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
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
Foreman, K.W., Nguyen, H.N., Ofori, L.O., Wanner, J., and Werner, D., WO Patent Appl. no. WO 2016/183359.
Lee, T.R. and Kim, K., J. Heterocycl. Chem., 1989, vol. 26, p. 747. https://doi.org/10.1002/jhet.5570260344
ACKNOWLEDGMENTS
The work was performed using the equipment of the Baikal Analytical Center for Collective Use, Siberian Branch, Russian Academy of Sciences.
Author information
Authors and Affiliations
Corresponding author
Ethics declarations
The authors declare no conflict of interest.
Rights and permissions
About this article
Cite this article
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
Received:
Revised:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1134/S1070428020050164