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Study of alkaloids of the Siberian and Altai flora

12. Synthesis of new lappaconitine derivatives containing olefinic substituents

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Russian Chemical Bulletin Aims and scope

Abstract

Lappaconitine and N-deacetyllappaconitine derivatives containing bromine and iodine atoms in the aromatic moiety were synthesized. The Heck cross-coupling of these halides with ethyl acrylate or 2-methyl-5-vinylpyridine afforded new olefinated lappaconitine derivatives.

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References

  1. N. V. Anferova, I. Yu. Bagryanskaya, Yu. V. Gatilov, S. A. Osadchii, M. M. Shakirov, E. E. Shults, and G. A. Tolstikov, Izv. Akad. Nauk, Ser. Khim., 2003, 2363 [Russ. Chem. Bull., Int. Ed., 2003, 52, 2500].

    Google Scholar 

  2. M. D. Mashkovskii, Lekarstvennye sredstva [Drugs], Torsing, Kharkov, 1998, 1, 380 (in Russian).

    Google Scholar 

  3. R. D. Kurbanov and T. A. Abdullaev, Klinicheskaya Meditsina [Clinical Medicine], 1988, 66, No. 10, 52 (in Russian).

    CAS  Google Scholar 

  4. A. S. Smetnev, S. P. Golitsin, and E. Z. Levin, Terapevticheskii Arkhiv [Therapeutical Archive], 1988, 60, No. 8, 34 (in Russian).

    CAS  Google Scholar 

  5. V. S. Gasilin, E. V. Dorofeev, and N. I. Rozova, Kardiologiya [Cardiology], 1990, 30, No. 9, 30 (in Russian).

    CAS  Google Scholar 

  6. M. S. Yunusov, Bashkir. Khim. Zh. [Bashkir. Chem. J.], 1997, 4, No. 4, 16 (in Russian).

    CAS  Google Scholar 

  7. F. N. Dzhakhangirov, M. N. Sultankhadzhaev, B. Tashkhodzhaev, and B. T. Salimov, Khim. Prirod. Soedin., 1997, 254 [Chem. Nat. Compd., 1997 (Engl. Transl.)].

  8. H. K. Desai, B. P. Hart, R. W. Caldwell, J. Huang, and S. W. Pelletier, J. Nat. Prod., 1998, 61, 743.

    Article  CAS  Google Scholar 

  9. F. N. Dzhakhangirov, Diterpenovye alkaloidy — novyi klass prirodnykh veshchestv s antiaritmicheskoi aktivnost’yu [Diterpene Alkaloids — A New Class of Natural Compounds with Antiarrhythmic Activity], in Azotistye geterotsikly I alkaloidy [Nitrogen Heterocycles and Alkaloids], Eds V. G. Kartsev and G. A. Tolstikov, Iridium-press, 2001, U2, 296 (in Russian).

  10. J. F. Heubach and A. Schuele, Planta Med., 1998, 64, 22.

    CAS  Google Scholar 

  11. T. G. Tolstikova, T. V. Voevoda, and M. P. Dolgikh, Eksp. Klinich. Farmak. [Exp. Clinic. Pharmacol.], 2001, 64, No. 4, 7 (in Russian).

    CAS  Google Scholar 

  12. U. T. Gutser, J. Friese, J. F. Heubach, T. Matthiesen, N. Selve, B. Wilffert, and J. Gleitz, Arch. Pharm., 1998, 357, 39.

    CAS  Google Scholar 

  13. Pat. RF 2180583; Byul. izobret. [Invention Bull.], 2002, 148 (in Russian).

  14. S. A. Osadchii, N. A. Pankrushina, M. M. Shakirov, E. E. Shults, and G. A. Tolstikov, Izv. Akad. Nauk, Ser. Khim., 2000, 552 [Russ. Chem. Bull., Int. Ed., 2000, 49, 557].

    Google Scholar 

  15. N. A. Pankrushina, I. A. Nikitina, N. V. Anferova, S. A. Osadchii, M. M. Shakirov, E. E. Shults, and G. A. Tolstikov, Izv. Akad. Nauk, Ser. Khim., 2003, 2354 [Russ. Chem. Bull., Int. Ed., 2003, 52, 2490].

    Google Scholar 

  16. S. A. Ross and S. W. Pelletier, Heterocycles, 1991, 32, 1307.

    Article  CAS  Google Scholar 

  17. N. V. Malykhina, S. A. Osadchii, M. M. Shakirov, E. E. Shults, and G. A. Tolstikov, Dokl. Akad. Nauk, 2004, 394, 343 [Dokl. Chem., 2004 (Engl. Transl.)].

    Google Scholar 

  18. Q.-H. Chen and F.-P. Wang, Chines Chem. Lett., 2001, 12, 421.

    CAS  Google Scholar 

  19. R. F. Heck, Palladium Reagents in Organic Synthesis, Academic Press, New York, 1985, 276.

    Google Scholar 

  20. J. Tsuji, Palladium Reagents and Catalysts: Innovation in Organic Chemistry, Wiley, Chichester, 1995, 95.

    Google Scholar 

  21. M. Larhed and A. Hallberg, The Heck Reaction, in Handbook of Organopalladium Chemistry for Organic Synthesis, Wiley, New York, 2002, 1133.

    Chapter  Google Scholar 

  22. I. P. Beletskaya and A. V. Cheprakov, Chem. Rev., 2000, 3009.

  23. US Pat. 5068392; Chem. Abstrs, 1992, 116, 83386.

    Google Scholar 

  24. P. A. Petyunin and M. E. Konshin, Zh. Obshch. Khim., 1957, 27, 475 [J. Gen. Chem. USSR, 1957, 27 (Engl. Transl.)].

    CAS  Google Scholar 

  25. P. Beinker, J. R. Hanson, N. Meindl, and I. C. R. Medina, J. Chem. Res. S., 1998, 4, 204.

    Article  Google Scholar 

  26. P. A. Galenko-Yaroshevskii, O. A. Chekanova, V. V. Skibitskii, V. V. Bartashevich, A. I. Khankoeva, and T. I. Polyashova, Byul. Eksp. Biol. Med., Farmak. Toksik. [Bull. Exp. Biol. Med., Pharmac. Toxic. (Engl. Transl.)].

  27. D. Barker, M. D. McLeod, M. A. Brimble, and G. P. Savage, Tetrahedron Lett., 2001, 42, 1785.

    Article  CAS  Google Scholar 

  28. H. Schulze, Arch. Pharm. Ber. Deutsch. Pharm. Ges., 1922, 260, 230.

    CAS  Google Scholar 

  29. G. B. Shul’pin, Organicheskie reaktsii, kataliziruemye kompleksami metallov [Metal Complex Catalyzed Organic Reactions], Nauka, Moscow, 1988, 275 (in Russian).

    Google Scholar 

  30. Y. Takahashi, Ts. Ito, S. Sakai, and Y. Ishii, Chem. Commun., 1970, 1065.

  31. J. B. Stothers, Carbon-13 NMR Spectroscopy, Academic Press, New York—London, 1972.

    Google Scholar 

  32. W. Bremser, L. Ernst, B. Franke, R. Gerhards, and A. Hardt, Carbon-13 NMR Spectral Data, 4th ed., Verlag Chemie, 1987, Spectrum No. 36303.

  33. S. G. Davies, C. J. Goodwin, D. Pyatt, and A. D. Smith, J. Chem. Soc., Perkin Trans. 1, 2001, 1413.

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Authors and Affiliations

  1. N. N. Vorozhtsov Novosibirsk Institute of Organic Chemistry, Siberian Branch of the Russian Academy of Sciences, 9 prosp. Akad. Lavrent’eva, 630090, Novosibirsk, Russian Federation

    S. A. Osadchii, E. E. Shul’ts, E. V. Polukhina, M. M. Shakirov & G. A. Tolstikov

Authors
  1. S. A. Osadchii
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  2. E. E. Shul’ts
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  3. E. V. Polukhina
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  4. M. M. Shakirov
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  5. G. A. Tolstikov
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Dedicated to the memory of Academician V. A. Koptyug on the occasion of the 75th anniversary of his birth.

Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 6, pp. 1038–1044, June, 2006.

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Osadchii, S.A., Shul’ts, E.E., Polukhina, E.V. et al. Study of alkaloids of the Siberian and Altai flora. Russ Chem Bull 55, 1077–1084 (2006). https://doi.org/10.1007/s11172-006-0380-2

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  • DOI: https://doi.org/10.1007/s11172-006-0380-2

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