Skip to main content
SpringerLink
Log in

Synthesis of Sulfur-containing Heterocyclic Compounds Based on Isothiocyanate Derivatives of Perfluoroolefins. (Review)

  • Published:
Chemistry of Heterocyclic Compounds Aims and scope

    We’re sorry, something doesn't seem to be working properly.

    Please try refreshing the page. If that doesn't work, please contact support so we can address the problem.

Abstract

The paper reviews data on the synthesis of heterocyclic compounds with perfluoroalkyl groups based on the reaction of thiocyanate and isothiocyanate derivatives of perfluoroolefins with mononucleophilic reagents (C-, O-, S-, P-, and N-nucleophiles). It was shown that such derivatives are prospective synthons for the production of 1,3-thiazoles and 1,3-thiazolines. The factors affecting the formation of the heterocyclic system are identified.

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

Similar content being viewed by others

REFERENCES

  1. G. A. Olah, R. D. Chambers, and G. K. S. Prakash (eds.), Synthetic Fluorine Chemistry, Wiley, New York (1992).

    Google Scholar 

  2. N. Isikawa (Ed.), Advances in the Technology of Fluorine Compounds [Russian translation from Japanese], Mir, Moscow (1984).

    Google Scholar 

  3. S. Scheithauer and R. Mayer, in: A. Senning (ed.), Topics in Sulfur Chemistry, Georg Thieme Verlag, Stuttgart (1979), 4, p. 373.

    Google Scholar 

  4. J. Elguero, A. Fruchier, N. Jogerovic, and A. Werner, Org. Prep. Prod Int., 27, 33 (1995); Chem. Abstr., 122, 187437 (1995).

    Google Scholar 

  5. R. D. Chambers and C. R. Sargent, in: A. R. Katritzky and A. J. Boulton (eds.), Adv. Heterocycl. Chem., Academic Press, New York, 28, 1 (1981).

    Google Scholar 

  6. R. Filler, Y. Kobayashi, and L. M. Yagupolskii (eds.), Studies in Organic Chemistry. 48. Organofluorine Compounds in Medicinal Chemistry and Biomedical Applications, Elsevier, Amsterdam (1993), 386 pp.

    Google Scholar 

  7. J. T. Welch and S. Eswarakrishnan, Fluorine in Bioorganic Chemistry, Wiley, New York (1991).

    Google Scholar 

  8. R. Filler and Y. Kobayashi, Biomedical Aspects of Fluorine Chemistry, Elsevier Biomed. Press, Kodansha, Tokyo, New York (1982).

    Google Scholar 

  9. G. G. Furin, Chem. Rev., 20, Pt. 4, 1 (1996); Overseas Publ. Assoc. Amsterdam B. V., Published in The Netherlands by Horwood Acad. Publ. GmbH. Printed in Malaya.

    Google Scholar 

  10. G. G. Furin, Zh. Org. Khim., 30, 1704 (1994).

    Google Scholar 

  11. G. G. Furin, Targets Heterocycl. Syst., Italian Society Chemistry, Rome, 2, 355 (1998); Chem. Abstr., 131, 87838 (1999).

    Google Scholar 

  12. K. Burger, U. Wucherpfenning, and E. Brunner, Adv. Heterocycl. Chem., 60, 1 (1994); Chem. Abstr., 122, 187423 (1995).

    Google Scholar 

  13. S. K. Ritter and C. Washington, Chem. Eng. News, 73, 39 (1995).

    Google Scholar 

  14. K. Tanaka, Yuki Gosei Kagaku Kyokai Shi., 48, 16 (1990).

    Google Scholar 

  15. T. Obata, K. Fujii, Y. Fukuda, K. Tsutsuminchi, and Y. Yamanaka, Jpn. Patent 0504979 (1993); Chem. Abstr., 118, 207578 (1993).

    Google Scholar 

  16. S. Patai (ed.), The Chemistry of Cyanates and Their Thio Derivatives, Wiley, Chichester (1977).

    Google Scholar 

  17. V. Ya. Popkova, Dis. Dokt. Khim. Nauk v Vide Naychn. Dokl., Moscow (1995).

    Google Scholar 

  18. V. Ya. Popkova, M. Yu. Antipin, L. E. Vinogradova, L. A. Leites, and Yu. T. Struchkov, Heteroat. Chem., 3, 101 (1995).

    Google Scholar 

  19. A. B. Zolotoi, V. Ya. Popkova, M. Yu. Antipin, and Yu. T. Struchkov, Izv. Akad. Nauk, Ser. Khim., 343 (1992).

  20. V. Ya. Popkova, L. E. Vinogradova, L. A. Leites, and V. K. Osmanov, Izv. Akad. Nauk, Ser. Khim., 2366 (1991).

  21. V. Ya. Popkova and V. A. Nikanorov, Izv. Akad. Nauk SSSR. Ser. Khim., 2148 (1989).

  22. V. Ya. Popkova, E. I. Mysov, M. V. Galakhov, V. K. Osmanov, and L. S. German, Izv. Akad. Nauk SSSR. Ser. Khim., 2862 (1990).

  23. S. R. Sterlin, L. G. Zheravkova, B. L. Dyatkin, and I. L. Knunyants, Izv. Akad. Nauk SSSR. Ser. Khim., 2517 (1971).

  24. S. R. Sterlin, B. L. Dyatkin, L. G. Zhuravkova, and I. L. Knunyants, Izv. Akad. Nauk SSSR. Ser. Khim., 1176 (1969).

  25. G. G. Furin, Zh. Org. Khim., 31, 508 (1995).

    Google Scholar 

  26. V. Ya. Popkova, F. M. Dolgushin, M. Yu. Antipin, A. I. Yanovsky, Yu. T. Struchkov, and K. Burger, Heterocycles, 40, 1015 (1995).

    Google Scholar 

  27. G. G. Furin and E. L. Zhuzhgov, in: Abstracts of 12th European Symposium on Fluorine Chemistry, Berlin. Germany, 1998, PI-11.

  28. G. G. Furin, A. V. Rogoza, I. Yu. Bagryanskaya, and Yu. V. Gatilov, Zh. Org. Khim., 33, 787 (1997).

    Google Scholar 

  29. G. G. Furin and E. L. Zhuzhgov, Zh. Obshch. Khim., 67, 1560 (1997).

    Google Scholar 

  30. A. V. Rogoza and G. G. Furin, Zh. Org. Khim., 33, 777 (1997).

    Google Scholar 

  31. A. V. Rogoza, G. G. Furin, Yu. V. Gatilov, and I. Yu. Bagryanskaya, Izv. Akad. Nauk, Ser. Khim., 831 (1997).

  32. G. G. Furin and Yu. V. Gatilov, Khim. Geterotsikl. Soedin., 253 (1993).

  33. A. V. Rogoza, G. G. Furin, Yu. V. Gatilov, and I. Yu. Bagryanskaya, Izv. Akad. Nauk, Ser. Khim., 1027 (2001).

  34. G. G. Furin, I. Yu. Bagryanskaya, and Yu. V. Gatilov, Izv. Akad. Nauk, Ser. Khim., 1355 (1997).

  35. G. G. Furin, L. S. Pressman, A. V. Rogoza, and I. A. Salmanov, Zh. Org. Khim., 33, 782 (1997).

    Google Scholar 

  36. G. G. Furin, Yu. V. Gatilov, B. G. Kiriyanko, T. V. Rybalova, and E. L. Zhuzhgov, Zh. Org. Khim., 35, 1481 (1999).

    Google Scholar 

  37. G. G. Furin, in: Abstr. of 14th Intern. Symp. on Fluorine Chemistry, Yokohama, Japan (1994), p. 170.

  38. A. V. Rogoza and G. G. Furin, Zh. Obshch. Khim., 69, 1491 (1999).

    Google Scholar 

  39. G. G. Furin and E. L. Zhuzhgov, Zh. Obshch. Khim., 67, 1708 (1997).

    Google Scholar 

  40. G. G. Furin, L. S. Pressman, I. A. Salmanov, and E. L. Zhuzhgov, Zh. Obshch. Khim., 69, 1499 (1999).

    Google Scholar 

  41. G. G. Furin, I. Yu. Bagryanskaya, Yu. V. Gatilov, and E. K. Zhuzhgov, Izv. Akad. Nauk, Ser. Khim., 2021 (1998).

  42. T. Mukaiyama, H. Nambu, and M. Okamoto, J. Org. Chem., 27, 3651 (1962).

    Google Scholar 

  43. D. Barton and W.D. Ollis, Comprehensive Organic Chemistry [Russian translation], Vol. 3, Khimiya, Moscow (1982), p. 660.

    Google Scholar 

  44. Houben-Weyl, Methoden der Organischen Chemie, Thieme Verlag, Stuttgart, 1963, 12/1, p. 110.

    Google Scholar 

  45. A. V. Rogoza and G. G. Furin, Zh. Obshch. Khim., 68, 798 (1998).

    Google Scholar 

  46. S. A. Lermontov, I. M. Rakov, and I. V. Martynov, Sixth All-Union Conference on Organofluorine Compounds. Abstracts (1990), p. 193.

  47. A. V. Rogoza and G. G. Furin, Zh. Obshch. Khim., in press.

  48. V. Ya. Popkova, J. Fluor. Chem., 58, 343 (1992).

    Google Scholar 

  49. V. Ya. Popkova, K. Burger, and E. Herdtweck, J. Fluor. Chem., 75, 131 (1996).

    Google Scholar 

  50. Daikin Kogyo Co., Ltd., Jpn. Patent 8357371 (1983); Chem. Abstr., 99, 53740 (1983).

    Google Scholar 

Download references

Author information

Authors and Affiliations

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

    G. G. Furin

  2. Novosibirsk State University, Novosibirsk, Russia

    E. L. Zhuzhgov

Authors
  1. G. G. Furin
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. E. L. Zhuzhgov
    View author publications

    You can also search for this author in PubMed Google Scholar

Rights and permissions

Reprints and permissions

About this article

Cite this article

Furin, G.G., Zhuzhgov, E.L. Synthesis of Sulfur-containing Heterocyclic Compounds Based on Isothiocyanate Derivatives of Perfluoroolefins. (Review). Chemistry of Heterocyclic Compounds 38, 129–150 (2002). https://doi.org/10.1023/A:1015320822860

Download citation

  • Issue Date:

  • DOI: https://doi.org/10.1023/A:1015320822860

Search

Navigation