Skip to main content

Advertisement

Log in

Study of plant coumarins. 12*. Synthesis of 2-(1,2,3-triazolyl)-modified furocoumarins

  • Published:
Chemistry of Heterocyclic Compounds Aims and scope

Bromooreoselone reacted with sodium azide to give 2-azidooreoselone, which was highly reactive in a catalytic Huisgen reaction with various terminal alkynes. These reactions yielded 4-substituted 2-(triazol-1-yl)furocoumarins. The reaction of oreoselone azide with dimethyl acetylene-1,2-di-carboxylate gave 2-[(4,5-dimethoxycarbonyl)triazolyl]oreoselone and reaction with 7-ethynyl-6-methoxycarbonylcoumarin gave 1,4-dicoumarin-substituted 1,2,3-triazole.

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

Access this article

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. E. A. Makhneva, A. V. Lipeeva, E. E. Shults, M. M. Shakirov, and G. A. Tolstikov, Zh. Org. Khim., 48, 1097 (2012). [Russ. J. Org. Chem., 48, 1094 (2012)].

    Google Scholar 

  2. M. A. Lowes, A. M. Bowcock, and J. G. Krueger, Nature, 445, 866 (2007).

    Article  CAS  Google Scholar 

  3. L. D. Via, J. C. González-Gómez, L. G. Pérez-Montoto, L. Santana, E. Uriarte, S. M. Magno, and O. Gia, Bioorg. Med. Chem. Lett., 19, 2874 (2009).

    Article  Google Scholar 

  4. S. Chittaboina, F. Xie, and Q. Wang, Tetrahedron Lett., 46, 2331 (2005).

    Article  CAS  Google Scholar 

  5. B. H. M. Kuijpers, S. Groothuys, A. R. Keereweer, P. J. L. M. Quaedflieg, R. H. Blaauw, F. L. van Delft, and F. P. J. T. Rutjes, Org. Lett., 6, 3123 (2004).

    Article  CAS  Google Scholar 

  6. R. L. Weller and S. R. Rajski, Org. Lett., 7, 2141 (2005).

    Article  CAS  Google Scholar 

  7. N. A. Al-Masoudi, Y. A. Al-Soud, and A. Abdul-Zahra, Heteroat. Chem., 15, 380 (2004).

    Article  CAS  Google Scholar 

  8. M. Whiting, J. C. Tripp, Y.-C. Lin, W. Lindstrom, A. J. Olson, J. H. Elder, K. B. Sharpless, and V. V. Fokin, J. Med. Chem., 49, 7697 (2006).

    Article  CAS  Google Scholar 

  9. S. Palhågen, R. Canger, O. Henriksen, J. A. van Parys, M.-E. Rivière, and M. A. Karolchyk, Epilepsy Res., 43, 115 (2001).

    Article  Google Scholar 

  10. M. J. Genin, D. A. Allwine, D. J. Anderson, M. R. Barbachyn, D. E. Emmert, S. A. Garmon, D. R. Graber, K. C. Greda, J. B. Hester, D. K. Hutchinson, J. C. Morris, R. J. Reischer, C. W. Ford, G. E. Zurenco, J. C. Hamel, R. D. Schaadt, D. Stapert, and B. H. Yagi, J. Med. Chem. 43, 953 (2000).

    Article  CAS  Google Scholar 

  11. J. C. Morris, J. C. McMurtrie, S. E. Bottle, and K. E. Fairfull-Smith, J. Org. Chem., 76, 4964 (2011).

    Article  CAS  Google Scholar 

  12. Y. H. Lau, J. R. Price, M. H. Todd, and P. J. Rutledge, Chem.–Eur. J., 17, 2850 (2011).

    Article  CAS  Google Scholar 

  13. X.-P. He, Z. Song, Z.-Z. Wang, X.-X. Shi, K. Chen, and G.-R. Chen, Tetrahedron, 67, 3343 (2011).

    Article  CAS  Google Scholar 

  14. M.-K. Jeon, M.-K. Kang, and K. H. Park, Tetrahedron, 68, 6038 (2012).

    Article  CAS  Google Scholar 

  15. E. E. Shults, T. N. Petrova, M. M. Shakirov, E. I. Chernyak, L. M. Pokrovskii, S. A. Nekhoroshev, and G. A. Tolstikov, Chemistry for Sustainable Development [in Russian], 4, 683 (2003).

  16. V. V. Rostovtsev, L. G. Green, V. V. Fokin, and K. B. Sharpless, Angew. Chem., Int. Ed., 41, 2596 (2002).

    Article  CAS  Google Scholar 

  17. L.-T. Li, L.-F. Zhou, Y.-J. Li, J. Huang, R.-H. Liu, B. Wang, and P. Wang, Bioorg. Med. Chem. Lett., 22, 642 (2012).

    Article  CAS  Google Scholar 

  18. F. Reck, F. Zhou, M. Girardot, G. Kern, C. J. Eyermann, N. J. Hales, R. R. Ramsay, and M. B. Gravestock, J. Med. Chem., 48, 499 (2005).

    Article  CAS  Google Scholar 

  19. H. Hussain, J. Hussain, A. Al-Harrasi, and K. Krohn, Tetrahedron, 68, 2553 (2012).

    Article  CAS  Google Scholar 

  20. S. A. Osadchii, E. E. Shults, M. M. Shakirov, and G. A. Tolstikov, Izv. Akad. Nauk, Ser. Khim., 362 (2006). [Russ. Chem. Bull., 55, 375 (2006)].

  21. R. M. Claramunt, D. Sanz, C. Lόpez, J. A. Jiménez, M. L. Jimeno, J. Elguero, and A. Fruchier, Magn. Reson. Chem., 35, 35 (1997).

    Article  CAS  Google Scholar 

  22. 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., 56, 1261 (2007)].

  23. R. N. Nair, P. J. Lee, A. L. Rheingold, and D. B. Grotjahn, Chem.–Eur. J., 16, 7992 (2010).

    CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to E. E. Shults.

Additional information

*For Communication 11, see [1].

Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 4, pp. 591-601, April, 2012.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Lipeeva, A.V., Shults, E.E., Makhneva, E.A. et al. Study of plant coumarins. 12*. Synthesis of 2-(1,2,3-triazolyl)-modified furocoumarins. Chem Heterocycl Comp 49, 551–560 (2013). https://doi.org/10.1007/s10593-013-1281-6

Download citation

  • Received:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s10593-013-1281-6

Keywords

Navigation