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Synthesis of Amino Alcohols of the Cyclododecane and Decahydro-1,4-ethanonaphthalene Series

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Abstract

2-Aminocyclododecan-1-ol and 6(3)-aminodecahydro-1,4-ethanonaphthalen-5(2)-ols (mixture of isomers) were synthesized in two steps via oxidative hydroxybromination of cyclododecene and 1,2,3,4,4a,5,6,8a(1,4,4a,5,6,7,8,8a)-octahydro-1,4-ethanonaphthalines with the system hydrogen peroxide–HBr. In the first step, oxidation of hydrogen bromide with hydrogen peroxide generated intermediate dioxidanium bromide which added to the C=C double bond of the unsaturated substrate to give the corresponding α-bromo alcohols. In the second step, substitution of the bromine atom by amino group in the presence of an alkali afforded α-amino alcohols.

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REFERENCES

  1. Matheu, R., Ertem, M.Z., Grimbert-Surinach, C., Bent-Buchholz, J., Sala, X., and Llobet, A., ACS Catal., 2017, vol. 7, p. 6525. https://doi.org/10.1021/acscatal.7b01860

    Article  CAS  Google Scholar 

  2. Li, Zh., Gu, J., Qi, Sh., Wu, D., Gao, L., Chen, Z., Guo, J., Li, X., Wang, Y., Yang, X., and Tu, Y., J. Am. Chem. Soc., 2017, vol. 139, p. 14364. https://doi.org/10.1021/jacs.7b07965

    Article  PubMed  CAS  Google Scholar 

  3. Bergmeier, S.C., Tetrahedron, 2000, vol. 56, p. 2561. https://doi.org/10.1016/S0040-4020(00)00149-6

    Article  CAS  Google Scholar 

  4. Kas’yan, L.I. and Pal’chikov, V.A., Russ. J. Org. Chem., 2010, vol. 46, p. 1. https://doi.org/10.1134/S107042801001001X

    Article  CAS  Google Scholar 

  5. Kuehnel, M.F., Orchard, K.L., Dalle, K.E., and Reisner, E., J. Am. Chem. Soc., 2017, vol. 139, p. 7217. https://doi.org/10.1021/jacs.7b00369

    Article  PubMed  CAS  Google Scholar 

  6. Heinemann, F., Karges, J., and Gasser, G., Acc. Chem. Res., 2017, vol. 50, p. 2727. https://doi.org/10.1021/acs.accounts.7b00180

    Article  PubMed  CAS  Google Scholar 

  7. Korotkikh, N.I., Losev, G.A., Lipnitskii, V.F., Kalistratov, S.G., Sokolova, A.S., and Shvaika, O.P., Pharm. Chem. J., 1993, vol. 25, p. 67. https://doi.org/10.1007/BF00772856

    Article  Google Scholar 

  8. de Souza Fernandes, F., Fernandes, T.S., da Silveira, L.G., Caneschi, W., Lourenço, M.C.S, Diniz, C.G., de Oliveira, P.F., Martins, S.P.L., Pereira, D.E., Tavares, D.C., Le Hyaric, M., de Almeida, M.V., and Couri, M.R.C., Eur. J. Med. Chem., 2016, vol. 108, p. 203. https://doi.org/10.1016/j.ejmech.2015.11.037

    Article  PubMed  CAS  Google Scholar 

  9. Pal’chikov, V.A., Russ. J. Org. Chem., 2013, vol. 49, p. 787. https://doi.org/10.1134/S1070428013060018

    Article  CAS  Google Scholar 

  10. Kuliev, A.M., Khimiya i tekhnologiya prisadok k maslam i toplivam (Chemistry and Technology of Oil and Fuel Additives), Moscow: Khimiya, 1985.

  11. Mashkovskii, M.D., Lekarstvennye sredstva (Medicines), Moscow: Meditsina, 2002, 14th ed.

  12. Tandon, V.K., Kumar, M., Awasthi, A.K., Saxena, H.O., and Goswamy, G.K., Bioorg. Med. Chem. Lett., 2004, vol. 14, p. 3177. https://doi.org/10.1016/j.bmcl.2004.04.009

    Article  PubMed  CAS  Google Scholar 

  13. Kas’yan, L.I., Kas’yan, A.O., Okovityi, S.I., and Tarabara, I.N., Alitsiklicheskie epoksidnye soedineniya. Reaktsionnaya sposobnost’ (Alicyclic Epoxy Compounds. Reactivity), Dnepropetrovsk: Dnepropetr. Nats. Univ., 2003.

  14. Alimardanov, Kh.M., Sadygov, O.A., Suleimanova, E.T., Dzhafarova, N.A., Abdullaeva, M.Ya., and Babaev, N.R., Russ. J. Appl. Chem., 2009, vol. 82, p. 1255. https://doi.org/10.1134/S1070427209070180

    Article  CAS  Google Scholar 

  15. Malinovskii, M.S., Okisi olefinov i ikh proizvodnykh (Olefin Oxides), M.: Goskhimizdat, 1961.

  16. Sadygov, O.A., Alimardanov, Kh.M., and Ismailova, Sh.I., Russ. J. Gen. Chem., 2018, vol. 88, p. 862. https://doi.org/10.1134/S1070363218050031

    Article  CAS  Google Scholar 

  17. Martınez, A.G., Vilar, E.T., Fraile, A.G., de la Moya Cerero, S., and Martı́nez Ruiz, P., Tetrahedron: Asymmetry, 1998, vol. 9, no. 10, p. 1737. https://doi.org/10.1016/S0957-4166(98)00132-3

    Article  Google Scholar 

  18. Martı́nez, A.G., Vilar, E.T., Fraile, A.G., de la Moya Cerero, S., Martı́nez-Ruiz, P., and Villas, P.Ch., Tetrahedron: Asymmetry, 2002, vol. 13, p. 1. https://doi.org/10.1016/S0957-4166(02)00011-3

    Article  Google Scholar 

  19. Sadygov, O.A., Alimardanov, Kh.M., Ismailova, Sh.I., and Babaev, N.R., Russ. J. Gen. Chem., 2018, vol. 88, p. 650. https://doi.org/10.1134/S1070363218040072

    Article  CAS  Google Scholar 

  20. Alimardanov, Kh.M., Sadigov, O.A., Garibov, N.I., Dadashova, N.R., Almardanov, M.B., and Kuliev, A.D., Pet. Chem., 2017, vol. 57, p. 415. https://doi.org/10.1134/S0965544117050024

    Article  CAS  Google Scholar 

  21. Alimardanov, Kh.M., Sadygov, O.A., Dzhalilova, A.A, Almardanova, M.B., and Kuliev, A.D., Azerb. Khim. Zh., 2015, no. 3, p. 67.

    Google Scholar 

  22. Colthup, N.B., Daly, L.H., and Wiberley, S.E., Introduction to Infrared and Raman Spectroscopy, Boston: Academic, 1990, 3rd ed.

  23. Derome, A.E., Modern NMR Techniques for Chemistry Research, Oxford: Pergamon, 1987.

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Authors and Affiliations

  1. Mamedaliev Institute of Petrochemical Processes, National Academy of Sciences of Azerbaijan, 1025, Baku, Azerbaijan

    O. A. Sadigov, H. M. Alimardanov, Sh. I. Ismailova & N. R. Babayev

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  1. O. A. Sadigov
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  2. H. M. Alimardanov
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  3. Sh. I. Ismailova
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  4. N. R. Babayev
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Correspondence to O. A. Sadigov.

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Sadigov, O.A., Alimardanov, H.M., Ismailova, S.I. et al. Synthesis of Amino Alcohols of the Cyclododecane and Decahydro-1,4-ethanonaphthalene Series. Russ J Org Chem 56, 1001–1005 (2020). https://doi.org/10.1134/S1070428020060068

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