Advertisement

Russian Chemical Bulletin

, Volume 67, Issue 12, pp 2316–2319 | Cite as

Efficient synthesis of 3,4-diarylpyrrole-2-carboxylates, the key fragments of natural antimitotic agents

  • E. A. SilyanovaEmail author
  • A. V. Samet
  • V. V. Semenov
Brief Communications
  • 7 Downloads

Abstract

Barton-Zard reaction of nitrostilbenes with ethyl isocyanoacetate carried out in EtOH in the presence of K2CO3 allowed us to minimize the formation of side products and to obtain 3,4-diarylpyrrole-2-carboxylates in high yields.

Key words

combretastatin analogs lamellarins nitrostilbenes ethyl isocyanoacetate Barton-Zard reaction 3,4-diarylpyrroles 

Preview

Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.

References

  1. 1.
    D. V. Demchuk, A. V. Samet, N. B. Chernysheva, V. I. Ushkarov, G. A. Stashina, L. D. Konyushkin, M. M. Raihstat, S. I. Firgang, A. A. Philchenkov, M. P. Zavelevich, L. M. Kuiava, V. F. Chekhun, D. Y. Blokhin, A. S. Kiselyov, M. N. Semenova, V. V. Semenov, Bioorg. Med. Chem., 2014, 22, 738.CrossRefGoogle Scholar
  2. 2.
    D. V. Tsyganov, L. D. Konyushkin, I. B. Karmanova, S. I. Firgang, Y. A. Strelenko, M. N. Semenova, A. S. Kiselyov, V. V. Semenov, J. Nat. Prod., 2013, 76, 1485.CrossRefGoogle Scholar
  3. 3.
    N. B. Chernysheva, A. S. Maksimenko, F. A. Andreyanov, V. P. Kislyi, Y. A. Strelenko, V. N. Khrustalev, M. N. Semenova, V. V. Semenov, Eur. J. Med. Chem., 2018, 146, 511.CrossRefGoogle Scholar
  4. 4.
    V. V. Semenov, M. N. Semenova, Russ. Chem. Rev., 2015, 84, 134.CrossRefGoogle Scholar
  5. 5.
    M. N. Semenova, D. V. Demchuk, D. V. Tsyganov, N. B. Chernysheva, A. V. Samet, E. A. Silyanova, V. P. Kislyi, A. S. Maksimenko, A. E. Varakutin, L. D. Konyushkin, M. M. Raihstat, A. S. Kiselyov, V. V. Semenov, ACS Comb.Sci., 20, 700–721; DOI: 10.1021/acscombsci.8b00113.Google Scholar
  6. 6.
    A. V. Samet, E. A. Sil´yanova, V. I. Ushkarov, M. N. Semenova, V. V. Semenov, Russ. Chem. Bull., 2018, 67, 858.CrossRefGoogle Scholar
  7. 7.
    D. H. R. Barton, S. Z. Zard, J. Chem. Soc., Chem. Commun., 1985, 1098.Google Scholar
  8. 8.
    D. H. R. Barton, J. Kervagoret, S. Z. Zard, Tetrahedron, 1990, 46, 7587.CrossRefGoogle Scholar
  9. 9.
    N. Ono, Heterocycles, 2008, 75, 243.CrossRefGoogle Scholar
  10. 10.
    H. Fan, J. Peng, M. T. Hamann, J.-F. Hu, Chem. Rev., 2008, 108, 264.CrossRefGoogle Scholar
  11. 11.
    N. Ono, H. Miyagawa, T. Ueta, T. Ogawa, H. Tani, J. Chem. Soc. Perkin Trans. 1, 1998, 1595.Google Scholar
  12. 12.
    A. Bhattacharya, S. Cherukuri, R. E. Plata, N. Patel, V. Tamez, J. A. Grosso, M. Peddicord, V. A. Palaniswamy, Tetrahedron Lett., 2006, 47, 5481.CrossRefGoogle Scholar
  13. 13.
    P. Bobál, D. A. Lightner, J. Heterocycl. Chem., 2001, 38, 527.aaaaaaaaCrossRefGoogle Scholar
  14. 14.
    J. A. Pfefferkorn, D. M. Bowles, W. Kissel, D. C. Boyles, C. Choi, S. D. Larsen, Y. Song, K.-L. Sun, S. R. Miller, B. K. Trivedi, Tetrahedron, 2007, 63, 8124.CrossRefGoogle Scholar
  15. 15.
    Q. F. Liu, Adv. Mater. Res., 2014, 884–885, 465.Google Scholar
  16. 16.
    H. Uno, M. Tanaka, T. Inoue, N. Ono, Synthesis, 1999, 471.Google Scholar
  17. 17.
    J. G. Greger, S. J. P. Yoon-Miller, N. R. Bechtold, S. A. Flewelling, J. P. MacDonald, C. R. Downey, E. A. Cohen, E. T. Pelkey, J. Org. Chem., 2011, 76, 8203.CrossRefGoogle Scholar
  18. 18.
    U. Robben, I. Lindner, W. Gärtner, J. Am. Chem. Soc., 2008, 130, 11303.CrossRefGoogle Scholar
  19. 19.
    M. Caldarelli, J. Habermann, S. V. Ley, J. Chem. Soc., Perkin Trans. 1, 1999, 107.Google Scholar

Copyright information

© Springer Science+Business Media, LLC, part of Springer Nature 2018

Authors and Affiliations

  • E. A. Silyanova
    • 1
    Email author
  • A. V. Samet
    • 1
  • V. V. Semenov
    • 1
  1. 1.N. D. Zelinsky Institute of Organic ChemistryRussian Academy of SciencesMoscowRussian Federation

Personalised recommendations