Advertisement

Chemistry of Heterocyclic Compounds

, Volume 45, Issue 3, pp 317–326 | Cite as

Dzhemilev reaction in the synthesis of five-membered sulfur and selenium heterocycles*

  • V. A. D’yakonovEmail author
  • A. G. Ibragimov
  • L. M. Khalilov
  • A. A. Makarov
  • R. K. Timerkhanov
  • R. A. Tuktarova
  • O. A. Trapeznikova
  • L. F. Galimova
Article

A one-pot methods were developed for the synthesis of five-membered sulfur and selenium heterocycles based on the consecutive cyclometallation of olefins, allenes, and acetylenes using alkyl and haloalkyl derivatives of Al and Mg in the presence of catalytic amounts of titanium and zirconium complexes to give the corresponding alumina- and magnesacarbocycles in situ, which, without further purification, were introduced into reaction with sulfur or selenium, leading to various tetrahydrothiophenes, thiophenes, tetrahydroselenophenes, and selenophenes.

Keywords

aluminacyclopentanes magnesacyclopentanes selenophenes tetrahydroselenophenes tetrahydrothiophenes thiophenes metal complex synthesis 

Preview

Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.

References

  1. 1.
    S. Gronowitz (editor), Thiophene and its Derivatives, Part 1, J. Wiley & Sons, New York (1985), p. 1.Google Scholar
  2. 2.
    L. I. Belen'kii, E. P. Zakharov, M. A. Kalik, V. P. Litvinov, F. M. Stoyanovich, S. Z. Taits, and B. P. Fabrichnyi, New Directions in Thiophene Chemistry [in Russian], Nauka, Moscow (1976), 424 pp.Google Scholar
  3. 3.
    L. I. Belen'kii, in: L. I. Belen'kii (editor), Preparation and Properties of Organosulfur Compounds [in Russian], Khimiya, Moscow (1998); p. 344.Google Scholar
  4. 4.
    Yu. K. Yur'ev, Zh. Obshch. Khim., 6, 1669 (1936).Google Scholar
  5. 5.
    Belg. Pat. 623801; Chem. Abstr., 59, 8705 (1963).Google Scholar
  6. 6.
    P. J. Fagan, W. A. Nugent, and J. C. Calabrese, J. Am. Chem. Soc., 116, 1880 (1994).CrossRefGoogle Scholar
  7. 7.
    M. Mizza-Aghayan, R. Boukherroub, G. Etemad-Moghadam, G. Manuel, and M. Koenig, Tetrahedron Lett., 37, 3109 (1996).CrossRefGoogle Scholar
  8. 8.
    M. Zablocka, A. Igau, B. Donnadieu, J. P. Majoral, A. Skowronska, and P. Meunier, J. Chem. Soc., Chem. Commun., 1239 (1997).Google Scholar
  9. 9.
    Y. Miguel, A. Igau, B. Donnadieu, J. P. Majoral, N. Pirio, and P. Meunier, J. Chem. Soc., Chem. Commun., 279 (1997).Google Scholar
  10. 10.
    U. M. Dzhemilev and A. G. Ibragimov, J. Organomet. Chem., 466, 1 (1994).CrossRefGoogle Scholar
  11. 11.
    U. M. Dzhemilev and A. G. Ibragimov, Izv. Akad. Nauk, Ser. Khim., 816 (1998).Google Scholar
  12. 12.
    U. M. Dzhemilev and A. G. Ibragimov, Usp. Khim., 69, 134 (2000).Google Scholar
  13. 13.
    U. M. Dzhemilev, Tetrahedron, 51, 4333 (1995).CrossRefGoogle Scholar
  14. 14.
    U. M. Dzhemilev and A. G. Ibragimov, Usp. Khim., 74, 886 (2005).Google Scholar
  15. 15.
    U. M. Dzhemilev, A. G. Ibragimov, A. P. Zolotarev, and G. A. Tolstikov, Izv. Akad. Nauk SSSR, Ser. Khim., 1444 (1989).Google Scholar
  16. 16.
    U. M. Dzhemilev, A. G. Ibragimov, A. P. Zolotarev, R. R. Muslukhov, and G. A. Tolstikov, Izv. Akad. Nauk SSSR, Ser. Khim., 2831 (1990).Google Scholar
  17. 17.
    U. M. Dzhemilev, A. G. Ibragimov, A. B. Morozov, R. R. Muslukhov, and G. A. Tolstikov, Izv. Akad. Nauk SSSR, Ser. Khim., 1607 (1991).Google Scholar
  18. 18.
    U. M. Dzhemilev, A. G. Ibragimov, R. R. Gilyazev, and L. O. Khafizova, Tetrahedron, 60, 1281 (2004).CrossRefGoogle Scholar
  19. 19.
    U. M. Dzhemilev, A. G. Ibragimov, A. P. Zolotarev, L. M. Khalilov, and R. R. Muslukhov, Izv. Akad. Nauk SSSR, Ser. Khim., 386 (1992).Google Scholar
  20. 20.
    L. O. Khafizova, A. G. Ibragimov, G. N. Gil'fanova, L. M. Khalilov, and U. M. Dzhemilev, Izv. Akad. Nauk, Ser. Khim., 2089 (2001).Google Scholar
  21. 21.
    A. G. Ibragimov, L. O. Khafizova, G. N. Gil'fanova, and U. M. Dzhemilev, Izv. Akad. Nauk, Ser. Khim., 2095 (2002).Google Scholar
  22. 22.
    U. M. Dzhemilev, A. G. Ibragimov, L. O. Khafizova, L. P. Yakupova, and L. M. Khalilov, Zh. Org. Khim., 40, 684 (2004).Google Scholar
  23. 23.
    V. A. D'yakonov, E. Sh. Finkelshtein, and A. G. Ibragimov, Tetrahedron Lett., 48, 8583 (2007).CrossRefGoogle Scholar
  24. 24.
    A. Gordon and R. Ford, Chemist's Companion [Russian translation], Mir, Moscow (1976), p. 301.Google Scholar
  25. 25.
    V. V. D'yakonov, R. K. Timerkhanov, A. G. Ibragimov, and U. M. Dzhemilev, Izv. Akad. Nauk, Ser. Khim., 2156 (2007).Google Scholar
  26. 26.
    U. M. Dzhemilev, A. G. Ibragimov, V. A. D'yakonov, and R. A. Zinnurova, Zh. Org. Khim., 43, 184 (2007).Google Scholar
  27. 27.
    S. T. Ioffe and A. M. Nesmeyanov, Methods in Organoelement Chemistry. Magnesium, Beryllium, Calcium, Strontium, Barium Subgroup [in Russian], Izd. Akad. Nauk SSSR, Moscow (1963); p. 561.Google Scholar
  28. 28.
    R. Kh. Freidlina, E. M. Brainina, and A. N. Nesmeyanov, Dokl. Akad. Nauk SSSR, 138, 1369 (1969).Google Scholar
  29. 29.
    P. Cagniant, Bull. Soc. Chim. France, 62 (1953).Google Scholar

Copyright information

© Springer Science+Business Media, Inc. 2009

Authors and Affiliations

  • V. A. D’yakonov
    • 1
    Email author
  • A. G. Ibragimov
    • 1
  • L. M. Khalilov
    • 1
  • A. A. Makarov
    • 1
  • R. K. Timerkhanov
    • 1
  • R. A. Tuktarova
    • 1
  • O. A. Trapeznikova
    • 1
  • L. F. Galimova
    • 1
  1. 1.Russian Academy of Science InstitutionInstitute of Petroleum Chemistry and Catalysis of the Russian Academy of SciencesUfaRussia

Personalised recommendations