Skip to main content
SpringerLink
Log in

Synthetic Transformations of Sesquiterpene Lactones. 8*. Synthesis of 13-(2-Oxofuro- [2,3-d]pyrimidin-3(2H)-yl)eudesmanolides

  • Published:
Chemistry of Heterocyclic Compounds Aims and scope

An aza-Michael reaction of isoalantolactone with 5-bromo- or 5-iodo-substituted uracils gave (11R)-13-[5-bromo(iodo)-2,4-dioxotetrahydropyrimidin-1-yl]eudesma-4(15)-en-8β,12-olides, which were highly active in Pd-catalyzed cross-coupling reaction with terminal alkynes. Copper-catalyzed Mannich reaction of (11R)-13-(5-ethynyl-2,4-dioxotetrahydropyrimidin-1-yl)eudesma-4(15)-en-8β,12-olide with secondary amines and formaldehyde was used for the synthesis of (11R)-13-[5-(diethyl-amino)propynyl]-, (11R)-13-[5-(pyrrolidinyl-1-yl)propynyl]-, (11R)-13-[5-(4-oxopiperidin-1-yl)-propynyl]-, (11R)-13-[5-(4-methylpiperazin-1-yl)propynyl]-, and (11R)-13-(5-{[2-(pyridin-3-yl)piperidin-1-yl]propynyl}-2,4-dioxotetrahydropyrimidin-1-yl)eudesmanolides. The treatment of 13-[5(propargyl-amino)tetrahydropyrimidin-1-yl]eudesmanolides with silver nitrate led to the corresponding (11R)-13-(2-oxofuro[2,3-d]pyrimidin-3(2H)-yl)eudesmanolides. The structures of two compounds were proved by X-ray structural analysis.

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

Fig 1

Similar content being viewed by others

References

  1. S. S. Patrushev, M. M. Shakirov, T. V. Rybalova, and E. E. Shul’ts, Zh. Org. Khim., 49, 1802 (2013). [Russ. J. Org. Chem., 49, 1783 (2013).]

    Article  CAS  Google Scholar 

  2. A. Gangjee, Y. Zeng, J. J. McGuire, and R. L. Kisliuk, J. Med. Chem., 48, 5329 (2005).

    Article  CAS  Google Scholar 

  3. F. Amblard, V. Aucagne, P. Guenot, R. F. Schinazi, and L. A. Agrofoglio, Bioorg. Med. Chem., 13, 1239 (2005).

    Article  CAS  Google Scholar 

  4. T. Gazivoda, M. Šokčević, M. Kralj, L. Šuman, K. Pavelić, E. De Clercq, G. Andrei, R. Snoeck, J. Balzarini, M. Mintas, and S. Raić-Malić, J. Med. Chem., 50, 4105 (2007).

    Article  CAS  Google Scholar 

  5. M. J. Robins, I. Nowak, V. K. Rajwanshi, K. Miranda, J. F. Cannon, M. A. Peterson, G. Andrei, R. Snoeck, E. De Clercq, and J. Balzarini, J. Med. Chem., 50, 3897 (2007).

    Article  CAS  Google Scholar 

  6. N. Foloppe, L. M. Fisher, R. Howes, P. Kierstan, A. Potter, A. G. S. Robertson, and A. E. Surgenor, J. Med. Chem., 48, 4332 (2005).

    Article  CAS  Google Scholar 

  7. Y. Miyazaki, Y. Maeda, H. Sato, M. Nakano, and G. W. Mellor, Bioorg. Med. Chem. Lett., 18, 1967 (2008).

    Article  CAS  Google Scholar 

  8. A. Zhao, X. Gao, Y. Wang, J. Ai, Y. Wang, Y. Chen, M. Geng, and A. Shang, Bioorg. Med. Chem., 19, 3906 (2011).

    Article  CAS  Google Scholar 

  9. X. Y. Jiao, D. J. Kopecky, J. S. Liu, J. Q. Liu, J. C. Jaen, M.G. Cardozo, R. Sharma, N. Walker, H. Wesche, S. Li, E. Farrelly, S.-H. Xiao, Z. Wang, and F. Kayser, Bioorg. Med. Chem. Lett., 22, 6212 (2012).

    Article  CAS  Google Scholar 

  10. P. A. Harris, D. Bandyopadhyay, S. B. Berger, N. Campobasso, C. A. Capriotti, J. A. Cox, L. Dare, J. N. Finger, S. J. Hoffman, K. M. Kahler, R. Lehr, J. D. Lich, R. Nagilla, R. T. Nolte, M. T. Ouellette, C. S. Pao, M. C. Schaeffer, A. Smallwood, H. H. Sun, B. A. Swift, R. D. Totoritis, P. Ward, R. W. Marquis, J. Bertin, and P. J. Gough, ACS Med. Chem. Lett., 4, 1238 (2013).

    Article  CAS  Google Scholar 

  11. A. V. Belovodskii, E. E. Shults, M. M. Shakirov, I. Yu. Bagryanskaya, Yu. V. Gatilov, and G. A. Tolstikov, Zh. Org. Khim., 46, 1710 (2010). [Russ. J. Org. Chem., 46, 1719 (2010).]

    Article  CAS  Google Scholar 

  12. E. E. Shults, A. V. Belovodskii, T. G. Tolstikova, M. P. Dolgikh, E. A. Morozova, and G. A. Tolstikov, RU Pat. 2413724; Byul. Izobret., No. 7, 10 (2011).

  13. E. E. Shul’ts, A. V. Belovodskii, M. M. Shakirov, Yu. V. Gatilov, A. G. Pokrovskii, M. A. Pokrovskii, and G. A. Tolstikov, Khim. Prirodn. Soedin., 48, 215 (2012). [Chem. Nat. Compd., 48, 238 (2012).]

    Article  Google Scholar 

  14. S. G. Klochkov, I. V. Anan’ev, S. A. Pukhov, and S. V. Afanas’eva, Khim. Geterotsikl. Soedin., 750 (2012). [Chem. Heterocycl. Compd., 48, 698 (2012).]

    Article  CAS  Google Scholar 

  15. F. J. B. Mendonca, Jr., J. V. dos Anjos, D. Sinou, S. J. de Melo, and R. M. Srivastava, Synthesis, 1890 (2007).

  16. N. Fresneau, M.-A. Hiebel, L. A. Agrofoglio, and S. Berteina-Raboin, Tetrahedron Lett., 53, 1760 (2012).

    Article  CAS  Google Scholar 

  17. T. G. Kraljević, A. Bistrović, M. Dedić, S. K. Pavelić, M. Sedić, and S. Raić-Malić, Tetrahedron Lett., 53, 5144 (2012).

    Article  Google Scholar 

  18. V. Aucagne, F. Amblard, and L. A. Agrofoglio, Synlett, 2406 (2004).

  19. A. Sniady, A. Durham, M. S. Morreale, A. Marcinek, S. Szafert, T. Lis, K. R. Brzezinska, T. Iwasaki, T. Ohshima, K. Mashima, and R. Dembinski, J. Org. Chem., 73, 5881 (2008).

    Article  CAS  Google Scholar 

  20. Z. Janeba, J. Balzarini, G. Andrei, R. Snoeck, E. De Clercq, and M. J. Robins, J. Med. Chem., 48, 4690 (2005).

    Article  CAS  Google Scholar 

  21. S. A. Osadchii, E. E. Shults, E. V. Polukhina, M. M. Shakirov, S. F. Vasilevskii, A. A. Stepanov, and G. A. Tolstikov, Izv. Akad. Nauk, Ser. Khim., 1215 (2007). [Russ. Chem. Bull., Int. Ed., 56, 1261 (2007).]

    Article  CAS  Google Scholar 

  22. V. T. Bauman, E. E. Shults, M. M. Shakirov, and G. A. Tolstikov, Zh. Org. Khim., 48, 1489 (2012). [Russ. J. Org. Chem., 48, 1473 (2012).]

    Article  CAS  Google Scholar 

  23. R. Csuk, C. Nitsche, R. Sczepek, S. Schwarz, and B. Siewert, Arch. Pharm. Chem. Life Sci., 346, 232 (2013).

    Article  CAS  Google Scholar 

  24. K. Nakanishi, Infrared Spectra and the Structure of Organic Compounds [Russian translation], Mir, Moscow (1965), p. 33.

    Google Scholar 

  25. F. H. Allen, Acta Crystallogr., Sect. B: Struct. Sci., B58, 380 (2002).

    Article  CAS  Google Scholar 

  26. M. Currie and G. A. Sim, J. Chem. Soc., Perkin Trans. 2, 400 (1973).

  27. R. S. Rowland and R. Taylor, J. Phys. Chem., 100, 7384 (1996).

    Article  CAS  Google Scholar 

  28. F. H. Allen, O. Kennard, D. G. Watson, L. Brammer, A. G. Orpen, and R. Taylor, J. Chem. Soc., Perkin Trans. 2, S1 (1987).

  29. U. M. Dzhemilev, N. R. Popod’ko, and E. V. Kozlova, Metal Complex Catalysis in Organic Synthesis [in Russian], Khimiya, Moscow (1999), p.104.

    Google Scholar 

  30. S. C. Srivastava, M. M. Mehra, G. K. Trivedi, and S. C. Bhattacharyya, Indian J. Chem., 9, 512 (1971).

    CAS  Google Scholar 

  31. A. S. Sadykov, Chemistry of Anabasis aphylla alkaloids [in Russian], Izd-vo Academy of Sciences of Uzbekistan SSR, Tashkent (1956), p. 166.

    Google Scholar 

  32. G. M. Sheldrick, SADABS. Version 2.01, Bruker AXS Inc. Madison, Wisconsin, USA (2004).

  33. G. M. Sheldrick, SHELXS-97 – Programs for Crystal Structure Analysis (Release 97-2), Univ. Göttingen, Germany (1997).

    Google Scholar 

  34. G. M. Sheldrick, SHELXL-97 – A Program for Exploiting the Redundancy of Area-detector X-ray Data, Univ. Göttingen, Germany (1999).

    Google Scholar 

Download references

This work was performed with financial support from the Russian Science Foundation (project 14-13-00822) and the Grants Council of the President of the Russian Federation (grant NSh-2625.2014.3).

The analytical and spectral studies were performed at the Collective Use Center of the Chemical Services Center, Siberian Branch of the Russian Academy of Sciences.

Author information

Authors and Affiliations

  1. N. N. Vorozhtsov Novosibirsk Institute of Organic Chemistry, Siberian Branch of the Russian Academy of Sciences, 9 Lavrentieva Ave., Novosibirsk, 630090, Russia

    S. S. Patrushev, M. M. Shakirov, T. V. Rybalova & E. E. Shults

  2. Novosibirsk State University, 2 Pirogova St., Novosibirsk, 630090, Russia

    S. S. Patrushev & E. E. Shults

Authors
  1. S. S. Patrushev
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. M. M. Shakirov
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. T. V. Rybalova
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. E. E. Shults
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to E. E. Shults.

Additional information

*For Communication 7, see [1].

Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 8, pp. 1155-1173, August, 2014.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Patrushev, S.S., Shakirov, M.M., Rybalova, T.V. et al. Synthetic Transformations of Sesquiterpene Lactones. 8*. Synthesis of 13-(2-Oxofuro- [2,3-d]pyrimidin-3(2H)-yl)eudesmanolides. Chem Heterocycl Comp 50, 1063–1080 (2014). https://doi.org/10.1007/s10593-014-1566-4

Download citation

  • Received:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s10593-014-1566-4

Keywords

Search

Navigation