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Synthesis of N-Hydroxyalkyl-1,5,3-Dithiazepanes Based on Amino Alcohols

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Chemistry of Heterocyclic Compounds Aims and scope

Catalytic methods were developed for the synthesis of N-hydroxyalkyl-1,5,3-dithiazepanes by recyclization of 1-oxa-3,6-dithiacycloheptane with amino alcohols and by intermolecular cyclization of 1,2-ethanedithiol with methoxymethylamino alcohols.

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References

  1. K. Ito and M. Sekiya, Chem. Pharm. Bull., 27, 1691 (1979).

    Article  CAS  Google Scholar 

  2. U. Wellmar, J. Heterocycl. Chem., 35, 1531 (1998).

    Article  CAS  Google Scholar 

  3. E. B. Rakhimova, I. V. Vasil'yeva, L. M. Khalilov, A. G. Ibragimov, and U. M. Dzhemilev, Khim. Geterotsikl. Soedin., 1132 (2012). [Chem. Heterocycl. Compd., 48, 1050 (2012).]

    Article  CAS  Google Scholar 

  4. E. B. Rakhimova, E. A. Efremova, I. S. Bushmarinov, A. S. Goloveshkin, L. M. Khalilov, A. G. Ibragimov, and U. M. Dzhemilev, Tetrahedron Lett., 53, 4225 (2012).

    Article  CAS  Google Scholar 

  5. K. L. Ameta, R. P. Pawar, and A. J. Domb, Bioactive Heterocycles: Synthesis and Biological Evaluation, Nova Science Publishers, Inc. (2013).

  6. E. B. Rakhimova, R. A. Ismagilov, R. A. Zainullin, N. F. Galimzyanova, and A. G. Ibragimov, Zh. Prikl. Khim., 1547 (2013). [Russ. J. Appl. Chem., 86, 1504 (2013).]

    Article  CAS  Google Scholar 

  7. Z. T. Niatshina, N. N. Murzakova, I. V. Vasilieva, E. B. Rakhimova, V. R. Akhmetova, and A. G. Ibragimov, ARKIVOC, viii, 141 (2011).

    Article  Google Scholar 

  8. N. N. Murzakova, E. B. Rakhimova, I. V. Vasilieva, K. I. Prokof’yev, A. G. Ibragimov, and U. M. Dzhemilev, Tetrahedron Lett., 52, 4090 (2011).

    Article  CAS  Google Scholar 

  9. B. P. Nikolsky (editor), Chemist’s Handbook [in Russian], Vol. 2, Goskhimizdat, Leningrad branch, Leningrad (1963), p. 193.

  10. E. B. Rakhimova, R. A. Ismagilov, R. A. Zainullin, A. G. Ibragimov, and U. M. Dzhemilev, Khim. Geterotsikl. Soedin., 1325 (2013). [Chem. Heterocycl. Compd., 49, 1237 (2013).]

    Article  CAS  Google Scholar 

  11. N. L. Weinberg and E. A. Brown, J. Org. Chem., 31, 4058 (1966).

    Article  CAS  Google Scholar 

  12. R. F. Borch and A. I. Hassid, J. Org. Chem., 37, 1673 (1972).

    Article  CAS  Google Scholar 

  13. D. M. Barnes, J. Barkalow, and D. J. Plata, Org. Lett., 11, 273 (2009).

    Article  CAS  Google Scholar 

  14. Yu. N. Kukushkin, Reactivity of Coordination Compounds [in Russian], Khimiya, Leningrad (1987), p. 288.

    Google Scholar 

  15. V. G. Kharchenko, T. I. Gubina, and I. A. Markushina, Zh. Org. Khim., 394 (1982).

  16. S. P. Voronin, T. I. Gubina, S. A. Trushin, I. A. Markushina, and V. G. Kharchenko, Khim. Geterotsikl. Soedin., 1458 (1989). [Chem. Heterocycl. Compd., 25, 1216 (1989).]

    Article  Google Scholar 

  17. G. V. Mokrov, A. M. Likhosherstov, V. P. Lezina, T. A. Gudasheva, I. S. Bushmarinov, and M. Yu. Antipin, Izv. Akad. Nauk, Ser. Khim., 1228 (2010). [Russ. Chem. Bull., Int. Ed., 59, 1254 (2010).]

    Article  CAS  Google Scholar 

  18. K. Krohn and S. Cludius-Brandt, Synthesis, 1344 (2010).

  19. G. M. Sheldrick, Acta Crystallogr., Sect. A: Found. Crystallogr., A64, 112 (2008).

    Article  Google Scholar 

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This work received financial support from the Russian Foundation for Basic Research (grants 13-03-12027 ofi_m, 14-03-00240-а, 14-03-97023-r_povolzhye_а), and NSh-2136.2014.3.

The authors would like to express their gratitude to V. A. Veklov from the laboratory of catalyst preparation, Institute of Petrochemistry and Catalysis, Russian Academy of Sciences, for the contribution of heterogeneous catalysts.

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Correspondence to E. B. Rakhimova.

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Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 5, pp. 782-787, May, 2014.

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Rakhimova, E.B., Ismagilov, R.A., Meshcheryakova, E.S. et al. Synthesis of N-Hydroxyalkyl-1,5,3-Dithiazepanes Based on Amino Alcohols. Chem Heterocycl Comp 50, 720–725 (2014). https://doi.org/10.1007/s10593-014-1526-z

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  • DOI: https://doi.org/10.1007/s10593-014-1526-z

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