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Synthesis of New Pinane-Type Hetarylsulfides

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Chemistry of Natural Compounds Aims and scope

New bicyclic thioterpenoids with heterocyclic fragments were prepared via reactions of (–)-β-pinene and its oxide with 1-phenyl-1H-tetrazole-5-thiol, 1-methylimidazole-2-thiol, and 4,6-dimethyl-2-pyrimidinesulfenylchloride.

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References

  1. R. Leurs, H. van der Goot, and H. Timmerman, Adv. Drug Res., 20, 217 (1991).

    Article  CAS  Google Scholar 

  2. M. D. Mashkovskii, Drugs [in Russian], 16th Ed., Revised, Corrected, and Supplemented, Novaya Volna, Moscow, 2010, 1216 pp.

  3. G. L. Vyshkovskii (ed.), Registry of Russian Drugs. Encyclopedia of Medicines [in Russian], 19th Ed., RLS-MEDIA, Moscow, 2010, 1368 pp.

    Google Scholar 

  4. L. E. Nikitina, N. P. Artemova, and V. A. Startseva, Natural and Thio-modified Monoterpenoids [in Russian], LAP LAMBERT, Germany, 2012, 167 pp.

    Google Scholar 

  5. L. E. Nikitina, V. A. Startseva, N. P. Artemova, L. Yu. Dorofeeva, I. V. Kuznetsov, S. A. Lisovskaya, N. P. Glushko, and M. P. Kutyreva, Pharm. Chem. J., 45, 664 (2012).

    Article  CAS  Google Scholar 

  6. L. E. Nikitina, V. A. Startseva, I. A. Vakulenko, I. M. Khismatulina, S. A. Lisovskaya, N. P. Glushko, and R. S. Fassakhov, Pharm. Chem. J., 43, 251 (2009).

    Article  CAS  Google Scholar 

  7. L. E. Nikitina, V. A. Startseva, S. A. Dieva, I. A. Vakulenko, and G. A. Shamov, Chem. Nat. Compd., 42, 178 (2006).

    Article  CAS  Google Scholar 

  8. G. A. Tolstikov, F. Ya. Kanzafarov, U. M. Dzhemilev, R. G. Kantyukova, and L. M. Zelenova, Zh. Org. Khim., 19, 2075 (1982).

    Google Scholar 

  9. L. E. Nikitina, V. A. Startseva, I. A. Vakulenko, and V. V. Plemenkov, Russ. J. Gen. Chem., 72, 974 (2002).

    Article  CAS  Google Scholar 

  10. M. Firdaus, L. Montero De Espinosa, and M. A. R. Meier, Macromolecules, 44, 7253 (2011).

    Article  CAS  Google Scholar 

  11. A. V. Bodrov, L. E. Nikitina, V. A. Startseva, O. A. Lodochnikova, R. Z. Musin, and O. I. Gnezdilov, Russ. J. Gen. Chem., 83, 80 (2013).

    Article  CAS  Google Scholar 

  12. D. I. Davies and M. I. Parrot, Tetrahedron Lett., 27, 2719 (1972).

    Article  Google Scholar 

  13. P. Brunelle, T. S. Sorensen, and C. Taeschler, J. Org. Chem., 66, 7294 (2001).

    Article  PubMed  CAS  Google Scholar 

  14. N. Biswas, S. Thomas, and A. Sarkar, Chem. Phys. Lett., 4, 248 (2009).

    Article  Google Scholar 

  15. M. Garner, D. R. Armstrong, and J. Reglinski, Bioorg. Med. Chem. Lett., 11, 1357 (1994).

    Article  Google Scholar 

  16. R. S. Balestrero, D. M. Forkey, and J. G. Russel, Magn. Reson. Chem., 24, 651 (1986).

    Article  CAS  Google Scholar 

  17. O. A. Lodochnikova, A. V. Bodrov, A. F. Saifina, L. E. Nikitina, and I. A. Litvinov, J. Struct. Chem., 54, 140 (2013).

    Article  CAS  Google Scholar 

  18. L. E. Nikitina, S. A. Dieva, V. V. Plemenkov, O. A. Lodochnikova, A. T. Gubaidullin, O. N. Kataeva, and I. A. Litvinov, Russ. J. Gen. Chem., 71, 1161 (2001).

    Article  CAS  Google Scholar 

  19. V. A. Startseva, L. E. Nikitina, N. P. Artemova, S. A. Dieva, and V. V. Plemenkov, Chem. Nat. Compd., 36, 587 (2000).

    Article  CAS  Google Scholar 

  20. L. E. Nikitina, V. A. Startseva, V. V. Plemenkov, S. A. Dieva, O. A. Lodochnikova, and I. A. Litvinov, Chem. Nat. Compd., 43, 263 (2007).

    Article  CAS  Google Scholar 

  21. G. Yu. Ishmuratov, M. P. Yakovleva, V. S. Tukhvatshin, R. F. Talipov, L. E. Nikitina, N. P. Artemova, V. A. Startseva, and A. G. Tolstikov, Chem. Nat. Compd., 50, 22 (2014).

    Article  CAS  Google Scholar 

  22. I. V. Kuznetsov, L. E. Nikitina, and V. A. Startseva, Khim. Interesakh Ustoich. Razvit., 2, 217 (2011).

    Google Scholar 

  23. G. M. Sheldrick, SADABS, University of Goettingen, Goettingen, Germany, 2004.

    Google Scholar 

  24. G. M. Sheldrick, Acta Crystallogr., Sect. A: Found. Crystallogr., 64, 112 (2008).

  25. G. M. Sheldrick, SHELXL-97: Program for Crystal Structure Refinement, University of Goettingen, Goettingen, Germany, 1997.

    Google Scholar 

  26. L. J. Farrugia, J. Appl. Crystallogr., 4, 837 (1999).

    Article  Google Scholar 

  27. APEX (Version 2.1), SAINTPlus. Data Reduction and Correction Program. Version 7.31A, Bruker Advanced X-ray Solutions, BrukerXS Inc., Madison, Wisconsin (USA), 2006.

  28. A. L. Spek, Acta Crystallogr., Sect. A: Found. Crystallogr., 46, c34 (1990).

  29. V. K. Osmanov, Dissertation, KNITU, Kazan, 2009, 283 pp.

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Acknowledgment

The work was performed under the auspices of state support for K(VR)FU for improving its competitiveness as a leading world-wide scientific and educational center.

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Correspondence to L. E. Nikitina.

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Translated from Khimiya Prirodnykh Soedinenii, No. 4, July–August, 2014, pp. 566–570.

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Startseva, V.A., Bodrov, A.V., Aref’ev, A.V. et al. Synthesis of New Pinane-Type Hetarylsulfides. Chem Nat Compd 50, 652–657 (2014). https://doi.org/10.1007/s10600-014-1045-2

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