Advertisement

Chemistry of Heterocyclic Compounds

, Volume 47, Issue 11, pp 1367–1371 | Cite as

2-Phenylpyrrole: one-pot selective synthesis from acetophenone oxime and acetylene by a Trofimov reaction*

  • A. I. MikhalevaEmail author
  • O. V. Petrova
  • L. N. Sobenina
Article

We have developed a technologically orientated, one-pot way of synthesis of high purity 2-phenylpyrrole in 74% yield by treatment of acetophenone oxime with acetylene in the KOH–DMSO system. The reaction is carried out at 135-150°C under an acetylene atmospheric pressure. The synthesis was performed in laboratory (glass apparatus) and in a large scale (10 l reaction vessel).

Keywords

acetylene acetophenone oxime 2-phenylpyrrole 

Notes

This work was carried out with the financial support of the Russian Foundation for Fundamental Investigations (grants 08-03-12008-ofi, 10-03-91154-GFEN_a) and the Grants Council of the President of the Russian Federation (grant NSh 3230.2010.3).

References

  1. 1.
    G. Stemp and C. N. Johnson, US Pat. Appl. 5637609; Chem. Abstr., 123, 55690 (1995).Google Scholar
  2. 2.
    B. B. Lohray, V. B. Lohray, and V. K. G. Barot, US Pat. Appl. 6987123.Google Scholar
  3. 3.
    G. Zoller, R. Beyerle, U. Schindler, R.-E. Nitz, and P. A. Martorana, US Pat. Appl. 4785010; Chem. Abstr., 111, 23384 (1989).Google Scholar
  4. 4.
    L. C. López Cara, M. E. Camacho, M. Dora Carrión, V. Tapias, M. A. Gallo, G. Escames, D. Acuña-Castroviejo, A. Espinosa, and A. Entrena, Eur. J. Med. Chem., 44, 2655 (2009).CrossRefGoogle Scholar
  5. 5.
    M. Verdoes, B. I. Florea, U. Hillaert, L. I. Willems, W. A. van der Linden, M. Sae-Heng, D. V. Filippov, A. F. Kisselev, G. A. van der Marel, and H. S. Overkleeft, ChemBioChem, 9, 1735 (2008).CrossRefGoogle Scholar
  6. 6.
    R. D. Stremel, RF Pat.204614, Byul. Izobr., No. 29, 264 (1995).Google Scholar
  7. 7.
    W. Kung and P. O. Vogelhut, US Pat. Appl. 4560534; Chem. Abstr., 103, 67869 (1985).Google Scholar
  8. 8.
    D. Dhanak, C. B. Reese, S. Romana, and G. Zappia, J. Chem. Soc., Chem. Commun., 903 (1986).Google Scholar
  9. 9.
    L. Filippini, M. Gusmeroli, and R. Riva, Tetrahedron Lett., 33, 1755 (1992).CrossRefGoogle Scholar
  10. 10.
    B. Sezen and D. Sames, J. Am. Chem. Soc., 125, 5274 (2003).CrossRefGoogle Scholar
  11. 11.
    F. Jafarpour, S. Rahiminejadan, and H. Hazrati, J. Org. Chem., 75, 3109 (2010).CrossRefGoogle Scholar
  12. 12.
    N. R. Deprez, D. Kalyani, A. Krause, and M. Sanford, J. Am. Chem. Soc., 128, 4972 (2006).CrossRefGoogle Scholar
  13. 13.
    S. A. Carabineiro, R. M. Bellabarba, P. T. Gomes, and I. M. Fonseca, Catal. Lett., 111, 221 (2006).CrossRefGoogle Scholar
  14. 14.
    Y. Yada, Y. Miyake, and Y. Nishibayashi, Organometallics, 27, 3614 (2008).CrossRefGoogle Scholar
  15. 15.
    B. A. Trofimov, S. E. Korostova, A. I. Mikhaleva, L. N. Balabanova, A. N. Vasil'ev, and M. V. Sigalov, USSR Inventor's Sertificate 601282; Byul. Izobr., No. 13, 79 (1978).Google Scholar
  16. 16.
    B. A. Trofimov and A. I. Mikhaleva, N-Vinylpyrroles [in Russian], Nauka, Novosibirsk (1984).Google Scholar
  17. 17.
    E. Abele and E. Lukevics, Heterocycles, 53, 2285 (2000).CrossRefGoogle Scholar
  18. 18.
    A. I. Mikhaleva and E. Yu. Schmidt, in: V. G. Kartsev (editor), Selected Methods for Synthesis and Modification of Heterocycles [in Russian], Vol. 1, IBS Press, Moscow (2002), p. 334.Google Scholar
  19. 19.
    R. J. Tedeschi, in: R. A. Meyers (editor), Encyclopedia of Physical Science and Technology, Vol. 1, 3rd ed., Acad. Press, San Diego (2004), p. 55.CrossRefGoogle Scholar
  20. 20.
    E. Abele and E. Lukevics, in: Z. Rappoport and J. F. Liebman (editors), The Chemistry of Hydroxylamines, Oximes and Hydroxamic Acids, , Wiley, Chichester (2008), p. 241.Google Scholar
  21. 21.
    Z. Wang, in: Z. Wang (editor), Comprehensive Organic Name Reactions and Reagents, Part 3, Wiley, London (2009), p. 2793.Google Scholar
  22. 22.
    B. A. Trofimov, A. I. Mikhaleva, S. E. Korostova, A. N. Valil'ev, L. N. Balabanova, L. I. Sineva, and L. A. Ignat'eva, USSR Inventor's Sertificate 694505, Byul. Izobr., No. 40, 89 (1979).Google Scholar
  23. 23.
    B. A. Trofimov, A. I. Mikhaleva, L. N. Sobenina, and O. V. Petrova, RF Pat. 2397974, Byul. Izobr., No. 24 (2010).Google Scholar
  24. 24.
    B. A. Trofimov, in: A. R. Katritzky (editor), Advances in Heterocyclic Chemistry, Vol. 51, Academic Press, San Diego (1990), p. 177.CrossRefGoogle Scholar
  25. 25.
    B. A. Trofimov, in: R. A. Jones (editor), The Chemistry of Heterocyclic Compounds, Vol. 48, Part II, Wiley, New York (1992), p. 131.Google Scholar
  26. 26.
    B. A. Trofimov, Curr. Org. Chem., 6, 1121 (2002).CrossRefGoogle Scholar
  27. 27.
    B. A. Trofimov, Heterocyclic Acetylene Derivatives, Novel Polyfunctional Monomers, Reagents, and Intermediates [in Russian], Nauka, Moscow (1981), p. 14.Google Scholar

Copyright information

© Springer Science+Business Media, Inc. 2012

Authors and Affiliations

  • A. I. Mikhaleva
    • 1
    Email author
  • O. V. Petrova
    • 1
  • L. N. Sobenina
    • 1
  1. 1.A. E. Favorsky Irkutsk Institute of Chemistry, Siberian Branch, Russian Academy of SciencesIrkutskRussia

Personalised recommendations