Skip to main content
SpringerLink
Log in

Synthesis of heterocycles with polyfluoroalkyl substituents from unsaturated compounds containing polyfluoroalkyl groups. (Review)

  • Published:
Chemistry of Heterocyclic Compounds Aims and scope

Abstract

Methods for the construction of heterocyclic systems containing polyfluoroalkyl substituents from derivatives of ethylene and acetylene are discussed. It is shown that various compounds with polyfluoroalkyl groups can be used as building blocks: α,β-unsaturated carbonyl compounds, their synthetic organosilicon equivalents (silyl-substituted alcohols, silyl ethers of enols), and also sulfones, nitriles, polyfluoroalkenes (in reactions at the double bond), acetylenecarboxylic acids, their esters, and polyfluoroalkynes.

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.

Similar content being viewed by others

References

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

    Google Scholar 

  2. N. Ishikawa (Ed.), Fluorine Compounds, Modern Technology and Applications, Mir, Moscow, 1984.

    Google Scholar 

  3. S. Scheithauer and R. Mayer, in: A. Senning (editor), Topics in Sulfur Chemistry, Georg Thieme Publ., Vol. 4, Stuttgart (1979).

  4. J. Elguero, A. Fruchier, N. Jogerovic, and A. Werner, Org. Prep. Proced. Int., 27, 33 (1995).

    Article  CAS  Google Scholar 

  5. R. Filler, Y. Kobayashi, and L. M. Yagupolskii (editors), Studies in Organic Chemistry. 48. Organofluorine Compounds in Medicinal Chemistry and Biomedical Applications, Elsevier Sci. Publ., Amsterdam (1993).

    Google Scholar 

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

    Google Scholar 

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

    Google Scholar 

  8. K. Burger, U. Wucherpfenning, and E. Brunner, Adv. Heterocycl. Chem., 60, 1 (1994).

    CAS  Google Scholar 

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

    Google Scholar 

  10. R. D. Chambers and C. R. Sargent, Adv. Heterocycl. Chem., 28, 1 (1981).

    Article  CAS  Google Scholar 

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

    CAS  Google Scholar 

  12. G. G. Furin, Chemistry Rev., 20, Pt. 4, 1 (1996); OPA (Oversear Publishers Association), Amsterdam, Harwood Academic Publishers GmbH.

    Google Scholar 

  13. G. G. Furin, in: O. A. Attanasi and D. Spinelli (editors), Targets in Heterocyclic Systems (Chemistry and Properties), Italian Society of Chemistry, Roma, 2, 355 (1998).

    Google Scholar 

  14. G. G. Furin and E. L. Zhuzhgov, Khim. Geterotsikl. Soedin., 147 (2002).

  15. G. G. Furin, Adv. Heterocycl. Chem., 87, 273 (2004).

    Article  CAS  Google Scholar 

  16. B. Dondy and C. Portella, J. Org. Chem., 58, 6671 (1993).

    Article  CAS  Google Scholar 

  17. B. Dondy, P. Doussot, and C. Portella, Tetrahedron Lett., 35, 409 (1994).

    Article  CAS  Google Scholar 

  18. B. Dondy, P. Doussot, B. Didier, R. Plantier-Rouon, J. P. Bouillon, and C. Portella, in: Abstracts of 16th International Symposium on Fluorine Chemistry, Durham, England (2000), 1P-114.

  19. J.-P. Bouillon, B. Didier, B. Dondy, P. Doussot, R. Plantier-Royon, and C. Portella, Eur. J. Org. Chem., No. 1, 187 (2001); Chem. Abstr., 134, 266239 (2001).

  20. W.-Y. Huang, L. Lu, and Y. F. Zhang, Chin. J. Chem., 8, 281 (1990).

    Google Scholar 

  21. C. Zuczek, C. Gerardin-Charbonnier, S. Rocca, S. Thiebaut, and C. Selve, J. Fluorine Chem., 99, 41 (1999); Chem. Abstr., 113, 966994 (1990).

    Article  CAS  Google Scholar 

  22. K. Kato, M. Takemitsu, H. Mizumoto, K. Tokoyada, and S. Arai, Ger. Offen DE 19835866 (1999); Chem. Abstr., 130, 168166 (1999).

  23. J.-T. Liu and H.-J. Lu, J. Fluorine Chem., 111, 207 (2001).

    Article  CAS  Google Scholar 

  24. W.-Y. Huang, Y.-S. Liu, and L. Lu, Chin. Chem. Lett., 3, 583 (1992); Chem. Abstr., 118, 22131 (1993).

    CAS  Google Scholar 

  25. J.-T. Liu and H.-J. Lu, in: Abstracts of 13th European Symposium on Fluorine Chemistry, Bordeaux, France (2001), 1-P16.

  26. J.-T. Liu and H.-J. Lu, J. Fluorine Chem., 111, 213 (2001).

    Article  CAS  Google Scholar 

  27. H. Yamanaka, T. Takekawa, K. Morita, and T. Ishihara, Tetrahedron Lett., 37, 1829 (1996).

    Article  CAS  Google Scholar 

  28. H. Yamanaka and T. Ishihara, J. Fluorine Chem., 105, 295 (2000).

    Article  CAS  Google Scholar 

  29. W.-Y. Huang, Y.-S. Liu, and L. Lu, Chin. J. Chem., 12, 79 (1994); Chem. Abstr., 121, 9182 (1994).

    Article  CAS  Google Scholar 

  30. Q.-S. Hu, H.-P. Guan, and C.-M. Hu, J. Fluorine Chem., 75, 51 (1995).

    Article  CAS  Google Scholar 

  31. H.-P. Guan, Q.-S. Hu, and C.-M. Hu, Synthesis, 997 (1996).

  32. X.-C. Zhang and W.-Y. Huang, J. Fluorine Chem., 87, 57 (1998).

    Article  CAS  Google Scholar 

  33. X.-C. Zhang and W.-Y. Huang, Tetrahedron, 54, 12465 (1998).

    Google Scholar 

  34. Y.-S. Liu and W.-Y. Huang, J. Chem. Soc, Perkin Trans. 1, 981 (1997).

  35. A. Kameyama, Y. Hatakeyama, and T. Nishikubo, Tetrahedron Lett., 36, 2781 (1995).

    Article  CAS  Google Scholar 

  36. V. Kameswaran, Eur. Pat. Appl. EP 816337 (1998); Chem. Abstr., 128, 127929 (1998).

    Google Scholar 

  37. D. C. England, E. A. Donald, and F. J. Weigert, J. Org. Chem., 46, 144 (1981).

    Article  CAS  Google Scholar 

  38. W.-Y. Huang and L. Lu, Chin. J. Chem., 9, 167 (1991); Chem. Abstr., 115, 136068 (1991).

    Article  CAS  Google Scholar 

  39. S.-Z. Zhu, C.-Y. Qin, and B. Xu, J. Fluorine Chem., 79, 77 (1996).

    Article  CAS  Google Scholar 

  40. X.-Q. Tang and C.-M. Hu, J. Chem. Soc, Perkin Trans. 1, 2161 (1994).

  41. X.-Q. Tang and C.-M. Hu, J. Chem. Soc., Perkin Trans. 1, 1039 (1995).

  42. X.-Q. Tang and C.-M. Hu, Chin. Chem. Lett., 6, 281 (1995); Chem. Abstr., 123, 83264 (1995).

    CAS  Google Scholar 

  43. Q.-F. Wang, Y.-Y. Mao, and C.-M. Hu, J. Fluorine Chem., 94, 79 (1999).

    Article  CAS  Google Scholar 

  44. Q.-F. Wang, D. Hu, B.-H. Luo, and C.-M. Hu, Tetrahedron Lett., 39, 2377 (1998).

    Article  CAS  Google Scholar 

  45. B.-H. Luo, H.-P. Guan, and C.-M. Hu, Synlett, 1261 (1997).

  46. Q.-F. Wang, Y.-Y. Mao, S.-Z. Zhu, and C.-M. Hu, J. Fluorine Chem., 95, 141 (1999).

    Article  CAS  Google Scholar 

  47. D. Greif, U. Eilitz, M. Pulst, D. Riedel, and M. Weeks, J. Fluorine Chem., 94, 91 (1999).

    Article  CAS  Google Scholar 

  48. T. Ishihara, Jpn. Kokai Tokkyo Koho JP 01 22855 (1989); Chem. Abstr., 111, 134144 (1989).

  49. T. Ishihara, Y. Okata, M. Kuroboshi, T. Shinozaki, and T. Ando, Chem. Lett., 819 (1988); Chem. Abstr., 109, 210998 (1988).

    Google Scholar 

  50. R. D. Chambers, C. G. P. Jones, M. J. Silvester, and D. B. Speight, J. Fluorine Chem., 25, 47 (1984).

    Article  CAS  Google Scholar 

  51. X.-Q. Tang and C.-M. Hu, J. Fluorine Chem., 73, 133 (1995).

    Article  CAS  Google Scholar 

  52. X.-Q. Tang and C.-M. Hu, J. Chem. Soc, Chem. Commun., 631 (1994).

  53. X.-Q. Tang and C.-M. Hu, J. Fluorine Chem., 74, 9 (1995).

    Article  CAS  Google Scholar 

  54. V. Ya. Sosnovskikh, Yu. G. Yatluk, and V. A. Kutsenko, Izv. Akad. Nauk. Ser. Khim., 1825 (1999).

  55. G. G. Levkovskaya, G. V. Bozhenkov, L. I. Larina, I. T. Evstaf’eva, and A. N. Mirskova, Zh. Org. Khim., 37, 684 (2001).

    Google Scholar 

  56. H.-B. Yu and W.-Y. Huang, J. Fluorine Chem., 84, 65 (1997).

    Article  CAS  Google Scholar 

  57. B. Dondy, P. Doussot, M. Iznaden, M. Muzard, and C. Portella, Tetrahedron Lett., 35, 4357 (1994).

    Article  CAS  Google Scholar 

  58. P. P. Righetti, A. Gamra, G. Tacconi, and G. Desimoni, Tetrahedron, 37, 1779 (1981).

    Article  CAS  Google Scholar 

  59. D. C. England, J. Org. Chem., 46, 147 (1981).

    Article  CAS  Google Scholar 

  60. K. Burger, N. Sewald, E. Huber, and R. Ottlinger, Z. Naturforsch., 44b, 1298 (1989); Chem. Abstr., 113, 23805 (1990).

    Google Scholar 

  61. C Portella and B. Dondy, Tetrahedron Lett., 32, 83 (1991).

    Article  CAS  Google Scholar 

  62. B. Dondy, P. Doussot, and C. Portella, Synthesis, 995 (1992).

  63. P. Doussot and C. Portella, J. Org. Chem., 58, 6675 (1993).

    Article  CAS  Google Scholar 

  64. X.-C. Zhang and W.-Y. Huang, Synthesis, 51 (1999).

  65. H. Abele, A. Haas, M. Lieb, and M. Schelvis, J. Fluorine Chem., 84, 75 (1997).

    Article  CAS  Google Scholar 

  66. H.-B. Yu, Q.-S. Zhang, and W.-Y. Huang, Chin. J. Chem., 15, 278 (1997); Chem. Abstr., 127, 248004 (1997).

    Article  CAS  Google Scholar 

  67. Yu. Shermolovich and V. Timoshenko, J. Fluorine Chem., 114, 157 (2002).

    Article  CAS  Google Scholar 

  68. V. M. Timoshenko, Ya. V. Nikolin, N. P. Kolesnik, and Yu. G. Shermolovich, Zh. Org. Khim., 37, 666 (2001).

    Google Scholar 

  69. K. V. Komarov, N. D. Chkanikov, S. V. Sereda, M. Yu. Antipin, Yu. T. Struchkov, A. F. Kolomiets, and A. V. Fokin, Izv. Akad. Nauk SSSR. Ser. Khim., 2417 (1988); Chem. Abstr., 110, 192703 (1989).

    Google Scholar 

  70. K. V. Komarov, N. D. Chkanikov, S. V. Sereda, M. Yu. Antipin, Yu. T. Struchkov, A. F. Kolomiets, and A. V. Fokin, Izv. Akad. Nauk SSSR. Ser. Khim., 1920 (1988).

  71. A. F. Shidlovskii, A. Yu. Sizov, L. N. Luleshova, V. V. Nesterov, M. Yu. Antipin, A. S. Pereguzov, and N. D. Chkanikov, Izv. Akad. Nauk. Ser. Khim., 1261 (2000).

  72. A. V. Form and A. F. Kolomiyets, in: Abstracts of the Seventh Regular Meeting of Japanese-Soviet Fluorine Chemists, Fukuoka (1991), 2, p. 4–1.

    Google Scholar 

  73. A. S. Golubev, P. V. Pasternak, A. F. Shidlowskii, L. N. Saveleva, B. B. Averkin, V. N. Nesterov, M. Yu. Antipin, A. S. Peregudov, and N. D. Chkanikov, J. Fluorine Chem., 114, 63 (2002).

    Article  CAS  Google Scholar 

  74. W.-S. Huang, C.-Y. Yuan, and Z.-Q. Wang, J. Fluorine Chem., 74, 279 (1995).

    Article  CAS  Google Scholar 

  75. W.-S. Huang and C.-Y. Yung, Synthesis, 511 (1996).

  76. K. Uneyama, O. Morimoto, and F. Yamashita, Tetrahedron Lett., 36, 4821 (1986).

    Google Scholar 

  77. J.-B. Xiao, X.-M. Zhang, D.-I. Wang, and C.-G. Yuan, J. Fluorine Chem., 99, 83 (1999).

    Article  CAS  Google Scholar 

  78. H.-B. Yu, Q.-S. Zhang, and W.-Y. Huang, Chin. J. Chem., 15, 278 (1997); Chem. Abstr., 127, 248004 (1997).

    Article  CAS  Google Scholar 

  79. O. E. Petrova, M. A. Kurykin, and D. V. Gorlov, Izv. Akad. Nauk. Ser. Khim., 2195 (1999).

  80. H. Yamanaka, A. Murakami, M. Kuwabara, K. Fukunishi, and M. Norura, Nippon Kagaku Kaishi, 1864 (1989); Chem. Abstr., 112, 197575 (1990).

  81. H. Yamanaka, K. Tamura, K. Funabiki, K. Fukunishi, and T. Ishihara, J. Fluorine Chem., 57, 177 (1992).

    Article  CAS  Google Scholar 

  82. K. Funabiki, K. Tamura, T. Ishihara, and H. Yamanaka, Bull. Chem. Soc. Jpn., 67, 3021 (1994).

    CAS  Google Scholar 

  83. A. Chauvin, J. Greiner, R. Pastor, and A. Cambon, Tetrahedron, 42, 663 (1986).

    Article  CAS  Google Scholar 

  84. B. C. Hamper, M. L. Kurtzweil, and J. P. Beck, J. Org. Chem., 57, 5680 (1992).

    Article  CAS  Google Scholar 

  85. X.-Q. Tang and C.-M. Hu, J. Fluorine Chem., 73, 129 (1995).

    Article  Google Scholar 

  86. H.-B. Yu and W.-Y. Huang, J. Fluorine Chem., 87, 69 (1998).

    Article  CAS  Google Scholar 

  87. R. J. De Pasquale, C. D. Padgett, and R. W. Rosser, J. Org. Chem., 40, 810 (1975).

    Article  Google Scholar 

  88. N. P. Stepanova, N. A. Orlova, V. A. Galishev, E. S. Turbanova, and A. A. Petrov, Zh. Org. Khim., 21, 979 (1985).

    CAS  Google Scholar 

  89. E. S. Turbanova, N. P. Stepanova, V. A. Lebedev, V. A. Galishev, and A. A. Petrov, Zh. Org. Khim., 19, 221 (1983).

    CAS  Google Scholar 

  90. J. Froissard, J. Greiner, R. Pastor, and A. Cambon, J. Fluorine Chem., 26, 47 (1984).

    Article  CAS  Google Scholar 

  91. N. Seewald and K. Burger, Liebigs Ann. Chem., 947 (1992).

  92. G. Meazza and G. Zanardi, J. Fluorine Chem., 55, 199 (1991).

    Article  CAS  Google Scholar 

  93. Y.-C. Shen, J.-H. Zheng, and Y.-Z. Huang, Synthesis, 970 (1985).

  94. G. B. Blackwell, R. N. Haszeldine, and D. R. Taylor, J. Chem. Soc., Perkin Trans. 1, 1 (1983).

  95. R. E. Banks and S. N. Mohialdin, J. Fluorine Chem., 38, 289 (1988).

    Article  CAS  Google Scholar 

  96. V. M. Koshelev, T. D. Taruskanova, A. N. Chekhlov, N. V. Vasil’ev, and A. F. Gontar’, Izv. Akad. Nauk SSSR. Ser. Khim., 1445 (1989).

  97. R. E. Banks and S. N. Khaffaff, J. Fluorine Chem., 51, 407 (1991).

    Article  CAS  Google Scholar 

  98. K. Burger and R. Ottlinger, Chem.-Ztg., 101, 402 (1977).

    CAS  Google Scholar 

  99. Z. V. Safronova, L. A. Simonyan, Yu. V. Zeifman, and N. P. Gambaryan, Izv. Akad. Nauk SSSR. Ser. Khim., 1826 (1979).

  100. K. Burger, U. Wassmuth, and S. Penninger, J. Fluorine Chem., 20, 813 (1983).

    Article  Google Scholar 

  101. G. Meazza and G. Zanardi, J. Fluorine Chem., 67, 183 (1994).

    Article  CAS  Google Scholar 

  102. T. Mantani, T. Konno, T. Ishihara, and H. Yamanaka, Chem. Lett., 666 (2000); Chem. Abstr., 133, 176943 (2000).

    Google Scholar 

  103. A. Nezis, J. Fayn, and A. R. Cambon, J. Fluorine Chem., 53, 285 (1991).

    Article  CAS  Google Scholar 

  104. A. Nezis, J. Fayn, and A. R. Cambon, J. Fluorine Chem., 53, 297 (1991).

    Article  CAS  Google Scholar 

  105. R. D. Chambers, Synth. Fluorine Chem., 359 (1992).

  106. M. Nishida, Y. Hayakawa, M. Matsui, K. Shibata, and H. Muramatsu, J. Heterocycl. Chem., 29, 113 (1992).

    CAS  Google Scholar 

  107. A. B. Abubakar, B. L. Booth, N. N. Suliman, and A. E. Tipping, J. Fluorine Chem., 56, 359 (1992).

    Article  CAS  Google Scholar 

  108. M. G. Barlow, N. N. Suliman, and A. E. Tipping, J. Fluorine Chem., 70, 59 (1995).

    Article  CAS  Google Scholar 

  109. P. Muller and Z. Miao, Helv. Chim. Acta., 77, 1826 (1994).

    Article  Google Scholar 

  110. R. N. Warrener, D. Margetic, E. R. Tiekink, and R. A. Russel, Synlett, 197 (1997).

  111. B. C. Hamper and K. L. Leschinsky, J. Heterocycl. Chem., 40, 575 (2003).

    Article  CAS  Google Scholar 

  112. M. Kawabara, K. Fukunishi, M. Nomura, and H. Yamanaka, J. Fluorine Chem., 41, 227 (1988).

    Article  Google Scholar 

  113. R. D. Chambers, C. G. P. Jones, M. J. Silvester, and D. B. Speight, J. Fluorine Chem., 26, 47 (1984).

    Article  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, 630090

    G. G. Furin

Authors
  1. G. G. Furin
    View author publications

    You can also search for this author in PubMed Google Scholar

Additional information

__________

Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 3, pp. 323–360, March, 2006.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Furin, G.G. Synthesis of heterocycles with polyfluoroalkyl substituents from unsaturated compounds containing polyfluoroalkyl groups. (Review). Chem Heterocycl Compd 42, 285–319 (2006). https://doi.org/10.1007/s10593-006-0087-1

Download citation

  • Received:

  • Revised:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s10593-006-0087-1

Keywords

Search

Navigation