Skip to main content
SpringerLink
Log in

Study of alkaloids of the Siberian and Altai flora 14. Synthesis of alkaloid-based tertiary N-(3-arylprop-2-ynyl)amines

  • Published:
Russian Chemical Bulletin Aims and scope

Abstract

3-Arylprop-2-ynylamines containing the key fragment of known alkaloids of the Altai flora were synthesized by the Sonogashira and Mannich reactions.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Log in via an institution

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Institutional subscriptions

Similar content being viewed by others

References

  1. S. A. Osadchii, E. E. Shults, S. F. Vasilevskii, E. V. Polukhina, A. A. Stepanov, and G. A. Tolstikov, Izv. Akad. Nauk, Ser. Khim., 2007, 344 [Russ. Chem. Bull., Int. Ed., 2007, 56, 356].

    Google Scholar 

  2. V. M. Dembitsky and D. O. Levitsky, Nat. Prod. Commun., 2006, 1, 405.

    CAS  Google Scholar 

  3. V. M. Dembitskii, G. A. Tolstikov, and A. G. Tolstikov, Khim. Interes. Ustoichivogo Razvitiya, 2003, 11, 341 [Chem. Sustainable Development, 2003, 11 (Engl. Transl.)].

    CAS  Google Scholar 

  4. M. Konishi, H. Ohkuma, T. Tsuno, T. Oki, G. D. VanDuyne, and J. Clardy, J. Am. Chem. Soc., 1990, 112, 3715.

    Article  CAS  Google Scholar 

  5. M. A. Huffman, N. Yasuda, A. E. DeCamp, and E. J. J. Grabowski, J. Org. Chem., 1995, 60, 1590.

    Article  CAS  Google Scholar 

  6. M. Tramontini, Synthesis, 1973, 703.

  7. M. Tramontini and L. Anglioni, Tetrahedron, 1990, 46, 1791.

    Article  CAS  Google Scholar 

  8. S. V. Klyatskaya, E. V. Tret’yakov, and S. F. Vasilevskii, Izv. Akad. Nauk, Ser. Khim., 2002, 122 [Russ. Chem. Bull., Int. Ed., 2002, 51, 128].

    Google Scholar 

  9. K. Hattori, M. Miyata, and H. Yamamoto, J. Am. Chem. Soc., 1993, 115, 1151.

    Article  CAS  Google Scholar 

  10. M. Miura, M. Enna, K. Okuro, and M. Nomura, J. Org. Chem., 1995, 60, 4999.

    Article  CAS  Google Scholar 

  11. D. L. Musso, M. J. Clarke, J. L. Kelley, G. E. Boswell, and G. Chen, Org. Biomol. Chem., 2003, 1, 498.

    Article  CAS  Google Scholar 

  12. K. Sonogashira, Y. Tohda, and N. Hagihara, Tetrahedron Lett., 1975, 50, 4467.

    Article  Google Scholar 

  13. C. Mannich and F. T. Chang, Ber. Deutsch. Chem. Ges., 1933, 66, 418.

    Article  Google Scholar 

  14. J. J. Li, Name Reactions, Springer-Verlag, Berlin-Heidelberg, 2003.

    Google Scholar 

  15. L. W. Bieber and M. F. da Silva, Tetrahedron Lett., 2004, 45, 8281.

    Article  CAS  Google Scholar 

  16. K. Edo, T. Sakamoto, and H. Yamanaka, Chem. Pharm. Bull., 1978, 26, 3843.

    CAS  Google Scholar 

  17. H. Pfanz and G. Kirchner, Justus Liebigs Ann. Chem., 1958, 614, 149.

    Article  CAS  Google Scholar 

  18. E. J. Corey and A. Venkateswarlu, J. Am. Chem. Soc., 1972, 94, 6190.

    Article  CAS  Google Scholar 

  19. C. A. Osadchii, E. E. Shults, E. V. Polukhina, M. M. Shakirov, and G. A. Tolstikov, Izv. Akad. Nauk, Ser. Khim., 2006, 1038 [Russ. Chem. Bull., Int. Ed., 2006, 55, 1077].

    Google Scholar 

  20. V. B. Mochalin and T. S. Minervina, Zh. Org. Khim., 1965, 1, 1726 [J. Org. Chem. USSR, 1965, 1 (Engl. Transl.)].

    CAS  Google Scholar 

  21. N. Miyaura and A. Suzuki, in Organic Syntheses, 1993, Coll. Vol. 8, 532; 1990, Coll. Vol. 68, 130.

  22. G. Ferguson, R. McCrindle, A. J. McAlees, and M. Parvez, Acta Crystallogr., Sect. B, 1982, 38, 2679.

    Article  Google Scholar 

  23. T. A. Henry, The Plant Alkaloids, 4th ed., London, 1949.

  24. A. Orechov and G. Menschikoff, Ber. Deutsch. Chem. Ges., 1931, 64, 266.

    Article  Google Scholar 

  25. A. S. Sadykov, Khimiya alkaloidov Anabasis aphylla [Chemistry of Alkaloids from Anabasis aphylla], Izd-vo AN Uzb. SSR, Tashkent, 1956, 222 pp. (in Russian).

    Google Scholar 

  26. M. V. Tsarev, Dokl. Akad. Nauk SSSR, 1944, 42, 127 [Dokl. Chem., 1944 (Engl. Transl.)].

    Google Scholar 

  27. R. A. Konovalova, S. Yunusov, and A. P. Orekhov, Zh. Obshch. Khim., 1939, 9, 1356 [J. Gen. Chem. USSR, 1939, 9 (Engl. Transl.)].

    Google Scholar 

  28. V. G. Zakharov, N. I. Libizov, and Kh. A. Aslanov, Lekarstvennye veshchestva iz rastenii i sposoby ikh proizvodstva [Drugs from Plants and Methods of Their Production], Izd-vo FAN, Tashkent, 1980, 232 pp. (in Russian).

    Google Scholar 

  29. 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 

  30. M. Shamma and D. M. Hindenlang, Carbon-13 NMR Shift Assignments of Amines and Alkaloids, Plenum Press, New York-London, 1979, No. 24.

    Google Scholar 

  31. S. Takamatsu, K. Saito, S. Ohmiya, N. Ruangrundi, and J. Murakoshi, Phytochemistry, 1991, 30, 3793.

    Article  CAS  Google Scholar 

  32. T. Eckert and J. Ipaktschi, Monatsh. Chem., 1998, 129, 1035.

    CAS  Google Scholar 

  33. N. S. Khruscheva, N. M. Loim, V. I. Sokolov, and V. D. Makhaev, J. Chem. Soc., Perkin Trans. 1, 1997, 16, 2425.

    Article  Google Scholar 

  34. R. Contreras, F. Santiesteban, M. A. Paz-Sandoval, and B. Wrackmeyer, Tetrahedron, 1984, 40, 3829.

    Article  CAS  Google Scholar 

Download references

Author information

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. Shults, E. V. Polukhina, M. M. Shakirov & G. A. Tolstikov

  2. Institute of Chemical Kinetics and Combustion, Siberian Branch of the Russian Academy of Sciences, 3 ul. Institutskaya, 630090, Novosibirsk, Russian Federation

    S. F. Vasilevskii & A. A. Stepanov

Authors
  1. S. A. Osadchii
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. E. E. Shults
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. E. V. Polukhina
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. M. M. Shakirov
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. S. F. Vasilevskii
    View author publications

    You can also search for this author in PubMed Google Scholar

  6. A. A. Stepanov
    View author publications

    You can also search for this author in PubMed Google Scholar

  7. G. A. Tolstikov
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to E. E. Shults.

Additional information

Dedicated to the memory of Academician N. N. Vorozhtsov on the 100th anniversary of his birth.

Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 6, pp. 1215–1221, June, 2007.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Osadchii, S.A., Shults, E.E., Polukhina, E.V. et al. Study of alkaloids of the Siberian and Altai flora 14. Synthesis of alkaloid-based tertiary N-(3-arylprop-2-ynyl)amines. Russ Chem Bull 56, 1261–1267 (2007). https://doi.org/10.1007/s11172-007-0191-0

Download citation

  • Received:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s11172-007-0191-0

Key words

Search

Navigation