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Catalytic Synthesis of N-Aryl-1,5,3-dithiazocanes

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Abstract

An efficient procedure has been developed for the synthesis of N-aryl-1,5,3-dithiazocanes and 1,1′-biphenylenebis(1,5,3-dithiazocanes) by heterocyclization of N1,N1,N7,N7-tetramethyl-2,6-dithiaheptane-1,7-diamine with aromatic amines or 4,4′-methylene(or sulfonyl)dianiline in the presence of Sm(NO3)3·6H2O as catalyst.

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REFERENCES

  1. Pozharskii, A.F., Soldatenkov, A.T., and Katritzky, A.R., Heterocycles in Life and Society, Chichester: Wiley, 2011, 2nd ed.

  2. Katritzky, A.R. and Pozharskii, A.F., Handbook of Heterocyclic Chemistry, Amsterdam: Elsevier, 2000, 2nd ed.

  3. Mashkovskii, M.D., Lekarstvennye sredstva (Medicines), Moscow: Novaya Volna, 2008, 15th ed., p. 1119.

  4. Bioactive Heterocycles: Synthesis and Biological Evaluation, Ameta, K.L., Pawar, R.P., and Domb, A.J., New York: Nova Biomedical, 2013.

  5. Akhmetova, V.R. and Rakhimova, E.B., Russ. J. Org. Chem., 2014, vol. 50, p. 1711. https://doi.org/10.1134/S107042801412001X

    Article  CAS  Google Scholar 

  6. Rakhimova, E.B., Vasilieva, I.V., Khalilov, L.M., Ibragimov, A.G., and Dzhemilev, U.M., Chem. Heterocycl. Compd., 2012, vol. 48, p. 1050. https://doi.org/10.1007/s10593-012-1098-8

    Article  CAS  Google Scholar 

  7. Niatshina, Z.T., Murzakova, N.N., Vasilieva, I.V., Rakhimova, E.B., Akhmetova, V.R., and Ibragimov, A.G., Arkivoc, 2011, vol. 2011, part (viii), p. 141. https://doi.org/10.3998/ark.5550190.0012.810

    Article  Google Scholar 

  8. Murzakova, N.N., Rakhimova, E.B., Vasilieva, I.V., Prokof’yev, K.I., Ibragimov, A.G., and Dzhemilev, U.M., Tetrahedron Lett., 2011, vol. 52, p. 4090. https://doi.org/10.1016/j.tetlet.2011.05.097

    Article  CAS  Google Scholar 

  9. Rakhimova, E.B., Vasilieva, I.V., Khalilov, L.M., Ibragimov, A.G., and Dzhemilev, U.M., Russ. J. Org. Chem., 2011, vol. 47, p. 1300. https://doi.org/10.1134/S1070428011090065

    Article  CAS  Google Scholar 

  10. Rakhimova, E.B., Meshcheryakova, E.S., Khalilov, L.M., Ibragimov, A.G., and Dzhemilev, U.M., Russ. J. Org. Chem., 2014, vol. 50, p. 1613. https://doi.org/10.1134/S1070428014110128

    Article  CAS  Google Scholar 

  11. Rakhimova, E.B., Ozden, I.V., Meshcheryakova, E.S., Khalilov, L.M., and Ibragimov, A.G., Russ. J. Org. Chem., 2015, vol. 51, p. 1788. https://doi.org/10.1134/S1070428015120222

    Article  CAS  Google Scholar 

  12. Rakhimova, E.B., Ozden, I.V., Ibragimov, A.G., and Dzhemilev, U.M.,Russ. J. Org. Chem., 2016, vol. 52, p. 571. https://doi.org/10.1134/S1070428016040175

    Article  CAS  Google Scholar 

  13. Rakhimova, E.B., Ozden, I.V., and Ibragimov, A.G., Russ. J. Org. Chem., 2018, vol. 54, p. 961. https://doi.org/10.1134/S1070428018070011

    Article  CAS  Google Scholar 

  14. Khairullina, R.R., Akmanov, B.F., Tyumkina, T.V., Kunakova, R.V., and Ibragimov, A.G., Russ. J. Org. Chem., 2012, vol. 48, p. 175. https://doi.org/10.1134/S1070428012020042

    Article  CAS  Google Scholar 

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ACKNOWLEDGMENTS

The spectral and analytical data were obtained using the facilities of the Agidel joint center (Institute of Petrochemistry and Catalysis, Ufa Federal Research Center, Russian Academy of Sciences).

Funding

This study was performed in accordance with the research program of the Institute of Petrochemistry and Catalysis (Ufa Federal Research Center, Russian Academy of Sciences; project no. AAAA-A19-119022290010-9 for 2019–2021 “Metal Complex and Heterogeneous Catalysis in the Synthesis of Macroheterocycles and Heteroatom Compounds”), as well as under financial support by the Ministry of Science and Education of the Russian Federation (project no. 2019-05-595-000-058).

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Correspondence to E. B. Rakhimova.

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Rakhimova, E.B., Ozden, I.V. & Ibragimov, A.G. Catalytic Synthesis of N-Aryl-1,5,3-dithiazocanes. Russ J Org Chem 56, 544–547 (2020). https://doi.org/10.1134/S107042802003029X

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  • DOI: https://doi.org/10.1134/S107042802003029X

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