Advertisement

Russian Journal of General Chemistry

, Volume 89, Issue 8, pp 1620–1624 | Cite as

Synthesis of 1,3,3,5,5-Penta[1-(2,2-dimethyl-1,3-dioxolan-4-yl)methoxy]-1-[(1H-1,2,3-triazol-4-yl)alkoxy]cyclotriphosphazenes

  • V. P. MorgalyukEmail author
  • T. S. Strelkova
  • Yu. N. Kononevich
  • V. K. Brel
Article
  • 13 Downloads

Abstract

Based on 1,3,3,5,5-penta[1-(2,2-dimethyl-1,3-dioxolan-4-yl)methoxy]-1-chlorocyclotriphosphazene, a series of hybrid compounds was obtained by two-step synthesis. In the molecules of the compounds obtained, hydrophobic organic residues are attached to the cyclotriphosphazene nucleus via a linker. A dialkyl substituted 1,2,3-triazole synthesized by click-chemistry methodology from acetylenic cyclotriphosphazene derivatives and organic azides in the presence of Cu(I) can be used as a linker connecting pentadioxolane-substituted phosphazene core. The reaction proceeds regioselectively with the formation of 1,4-disubstituted 1,2,3-triazoles only.

Keywords

1,3,3,5,5-penta[1-(2,2-dimethyl-1,3-dioxolan-4-yl)methoxy]-1-chlorocyclotriphosphazene click-chemistry 1,2,3-triazole acetylenes organic azides 

Preview

Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.

Notes

Funding

This work was supported by the Russian Foundation for Basic Research (grant no. 18-03-00275) and the Ministry of Science and Higher Education of the Russian Federation using the scientific equipment of the Center for Molecular Structure Research of the Institute of Organoelement Compounds of the Russian Academy of Sciences.

References

  1. 1.
    Steed, J.W. and Atwood, J.L., Supramolecular Chemistry, Chichester: J. Wiley & Sons, 2000.Google Scholar
  2. 2.
    Teasdale, I. and Brüggemann, O., Polymers, 2013, vol. 5, p. 161. doi  https://doi.org/10.3390/polym5010161 CrossRefGoogle Scholar
  3. 3.
    Kedik, S.A., Zhavoronok, E.S., Sedishev, I.P., Panov, A.V., Suslov, V.V., Petrova, E.A., Sapel’nikov, M.D., Shatalov, D.O., and Eremin, D.V., Razrabotka i registratsiya lekarstvennykh sredstv, 2013, no. 4, p. 22.Google Scholar
  4. 4.
    Ogueri, K.S., Ivirico, J.L.E., Nair, L.S., Allcock, H.R., and Laurencin, C.T., Regen. Eng. Transl. Med., 2017, vol. 3, no. 1, p. 51. doi  https://doi.org/10.1007/s40883-017-0026-y CrossRefGoogle Scholar
  5. 5.
    Ullah, R.S., Wang, L., Yu, H., Abbasi, N.M., Akram, M., Abdin, Z., Saleem, M., Haroon, M., and Khan, R.U., RSC Adv., 2017, vol. 7, no. 38, p. 23363. doi  https://doi.org/10.1039/c6ra27103k CrossRefGoogle Scholar
  6. 6.
    Ullah, R.S., Wang, L., Yu, H., Haroon, M., Elshaarani, T., Naveed, K.R., Fahad, S., Khan, A., Nazir, A., Xia, X., and Teng, L., J. Mater. Sci., 2019, vol. 54, no. 1, p. 745. doi  https://doi.org/10.1007/s10853-018-2843-x CrossRefGoogle Scholar
  7. 7.
    Tian, Zh., Hess, A., Fellin, C.R., Nulwala, H., and Allcock, H.R., Macromolecules, 2015, vol. 48, no. 13, p. 4301. doi  https://doi.org/10.1021/acs.macromol.5b00946 CrossRefGoogle Scholar
  8. 8.
    Allcock, H.R., Laredo, W.R., Kellam, E.C., and Morford, R.V., Macromolecules, 2001, vol. 34, no. 4, p. 787. doi  https://doi.org/10.1021/ma001166n CrossRefGoogle Scholar
  9. 9.
    Morgalyuk, V.P., Strelkova, T.S., Pavlov, A.A., Buyanovskaya, A.G., Ostapchuk, P.N., Godovikov, I.A., and Brel’, V.K., Russ. J. Gen. Chem., 2017, vol. 87, no. 4, p. 739. doi  https://doi.org/10.1134/S1070363217040120 CrossRefGoogle Scholar
  10. 10.
    Liang, L. and Astruc, D., Coord. Chem. Rev., 2011, vol. 255, no. 23, p. 2933. Doi  https://doi.org/10.1016/j.ccr.2011.06.028 CrossRefGoogle Scholar
  11. 11.
    Kolarovič, A., Schnürch, M., and Mihovilovic, M.D., J. Org. Chem., 2011, vol. 76, no. 8, p. 2613. doi  https://doi.org/10.1021/jo1024927 CrossRefGoogle Scholar
  12. 12.
    Dheer, D., Singh, V., and Shanka, R., Bioorg. Chem., 2017, vol. 71, p. 30. doi  https://doi.org/10.1016/j.bioorg.2017.01.010 CrossRefGoogle Scholar
  13. 13.
    Katorov, D.V., Rudakov, G.F., Katorova, I. N., Yakushkov, A.V., Simonov, D.P., and Zhilin, V.F., Russ. Chem. Bull., 2012, vol. 61, no. 11, p. 2114. doi  https://doi.org/10.1007/s11172-012-0296-y CrossRefGoogle Scholar
  14. 14.
    Bulman, P.C., Stephenson, R.G., Harvey, J., and Slawin, A.M.Z., Synlett, 2016, vol. 27, no. 17, p. 2500. doi  https://doi.org/10.1055/s-0035-1562603 CrossRefGoogle Scholar
  15. 15.
    Gonzaga, D., Senger, M.R., de Carvalho da Silva, F., Ferreira, V.F., and Silva, F.P., Jr., Eur. J. Med. Chem., 2014, vol. 74, p. 461. doi  https://doi.org/10.1016/j.ejmech.2013.12.039 CrossRefGoogle Scholar
  16. 16.
    Gonzaga, D.T.G., Ferreira, L.B.G., Costa, T.E.M.M., von Ranke, N.L., Pacheco, P.A.F., Simoes, A.P.S., Arruda, J.C., Dantas, L.P., de Freitas, H.R., de Melo Reis, R.A., Penido, C., Bello, M.L., Castro, H.C., Rodrigues, C.R., Ferreira, V.F., Faria, R.X., and de Carvalho da Silva, F., Eur. J. Med. Chem., 2017, vol. 139, p. 698. doi  https://doi.org/10.1016/j.ejmech.2017.08.034 CrossRefGoogle Scholar

Copyright information

© Pleiades Publishing, Ltd. 2019

Authors and Affiliations

  • V. P. Morgalyuk
    • 1
    Email author
  • T. S. Strelkova
    • 1
  • Yu. N. Kononevich
    • 1
  • V. K. Brel
    • 1
  1. 1.A. N. Nesmeyanov Institute of Organoelement CompoundsRussian Academy of SciencesMoscowRussia

Personalised recommendations