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Regioselective ring opening in epoxides under the action of amines in water medium

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Abstract

Amino(bis-amino)derivatives of 2-propanol were synthesized by ring opening in epoxides under the action of amines in water medium using environmentally safe methods. The structure of the compounds obtained was established by elemental analysis and the IR, 1H and 13C NMR spectroscopy. It was found that these substances are effective bactericides. They suppress the growth of the sulfate-reducing bacteria and exhibit high anticorrosive properties.

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References

  1. Chao-Jun, L., Chem. Rev., 2005, vol. 105, p. 3095.

    Article  Google Scholar 

  2. Evans, G., Gibbs, T.J.K., Zenkins, R.L., Cales, S.J., Hursthouse, M.B., Platts, A.J., and Tomkinson, N.C.O., Angew. Chem., Int. Ed., 2008, vol. 47, p. 2820.

    Article  CAS  Google Scholar 

  3. Kas’yan, L.I., Kas’yan, A.O., Okovityi, S.I., and Tarabara, I.N., Atsyklicheskie epoksidnye soedineniya. Reaktsionnaya sposobnost’ (Acyclic Epoxy Compounds: Reactivity), Dnepropetrovsk: Dnepropetrovsk. Univ., 2003.

    Google Scholar 

  4. Malinovskii, M.S., Okisi olefinov i ikh proizvodnye (Olefine Oxides and Their Derivatives), Moscow: Gos. Khim. Inst., 1961.

    Google Scholar 

  5. Kas’yan, L.I., Prid’ma, S.A., Turov, A.V., Pal’chikov, V.A., Kasyan, A.O., and Karat, L.D., Zh. Org. Khim., 2009, vol. 45, no. 4, p. 520.

    Google Scholar 

  6. Chini, M., Crotti, P., and Macchia, F., Tetrahedron Lett., 1990, vol. 31, no. 32, p. 4661.

    Article  CAS  Google Scholar 

  7. Cherbulies, E., Yazgi, A., and Rabinowitz, J., Helv. Chim. Acta, 1961, vol. 144, no. 4, p. 1164.

    Article  Google Scholar 

  8. Hanumatharao, P., Sambosivarao, S.V., Soni, L.K., Gupta, A.K., and Kaskhelikar, S.C., Bioorg. Med. Chem. Lett., 2005, vol. 15, p. 3167.

    Article  Google Scholar 

  9. Shearer, B.G., Chao, E.Y., and Deaton, D.N., Bioorg. Med. Chem. Lett., 2007, vol. 17, p. 4670.

    Article  CAS  Google Scholar 

  10. Merkis, A.I., Novikene, L.L., Daukshas, V.K., Shaltite, Z.A., Milyuvene, L.I., and Gavelene, B.A., Zh. Prikl. Khim., 2003, vol. 76, no. 1, p. 166.

    Google Scholar 

  11. Huskens, J. and Reetz, M.T., Eur. J. Org. Chem., 1999, vol. 8, p. 1775.

    Article  Google Scholar 

  12. Azizi, N. and Saidi, M.R., Org. Lett., 2005, vol. 7, no. 17, p. 3649.

    Article  CAS  Google Scholar 

  13. Fernandez-Rodriguez, M.A., Shen, Q., and Hartwig, Z.F., J. Am. Chem. Soc., 2006, vol. 128, p. 2180.

    Article  CAS  Google Scholar 

  14. Zhu, D., Xu, L., Wu, F., and Wan, B., Tetrahedron Lett., 2006, vol. 47, p. 5781.

    Article  CAS  Google Scholar 

  15. Paut, L., Sen, T.K., and Panniyamurthy, T., Angew, Chem. Int. Ed., 2007, vol. 46, p. 20046

    Google Scholar 

  16. Placzek, A.T., Donelson, J.L., Trivedi, R., Gibbs, R.A., and de Suriya, K., Tetrahedron Lett., 2005, vol. 46, no. 52, p. 9029.

    Article  CAS  Google Scholar 

  17. Kleiner, Ch.M. and Schreiner, P.R., Chem. Commun., 2006, no. 41, p. 4315.

  18. Griot, F., Tetrahedron, 1963, vol. 19, p. 1661.

    Article  CAS  Google Scholar 

  19. Chapman, N.B. and Triggle, D.J., J. Chem. Soc., 1963, p. 1385.

  20. Potekhin, A.A. and Safonov, A.O., Zh. Org. Khim., 1981, vol. 17, no. 2, p. 379.

    CAS  Google Scholar 

  21. Geartner, V.R., J. Org. Chem., 1968, vol. 33, no. 2, p. 523.

    Article  Google Scholar 

  22. Kochetkov, N.K. and Vorotnikova, L.A., Zh. Obshch. Khim., 1959, vol. 29, no. 3, p. 532.

    CAS  Google Scholar 

  23. Kirk, D.N., Chem. Ind., 1973, p. 109.

  24. Metodika kontrolya mikrobiologicheskoi zarazhennosti neftepromyslobykh vod i otsenka zashchitnogo bakteritsidnogo deistviya reagentov (Procedure of Controle of the Microbiological Infection of the Oil Field Waters and Evaluation of the Protective Bactericide Action of Reagents), RD 39-3-973-89, Ufa: VNIISPT Neft’, 1984.

  25. Gonik, A.A., Serovodorodnaya korroziya I mery eio preduprezhdeniya (Hydrogen Sulfide Corrozions and Measures of its Prevention), Moscow: Nedra, 1966.

    Google Scholar 

  26. Smirnov, A.N., Pomerantseva, E.G., and Spasskaya, I.F., Zh. Obshch. Khim., 1964, vol. 34, no. 11, p. 3370.

    Google Scholar 

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Correspondence to E. G. Mamedbeili.

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Original Russian Text © A.G. Talybov, V.M. Abbasov, E.G. Mamedbeili, K.A. Kochetkov, 2010, published in Zhurnal Obshchei Khimii, 2010, Vol. 80, No. 9, pp. 1501–1506.

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Talybov, A.G., Abbasov, V.M., Mamedbeili, E.G. et al. Regioselective ring opening in epoxides under the action of amines in water medium. Russ J Gen Chem 80, 1819–1824 (2010). https://doi.org/10.1134/S1070363210090173

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  • DOI: https://doi.org/10.1134/S1070363210090173

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