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Chemistry of Heterocyclic Compounds

, Volume 49, Issue 12, pp 1691–1714 | Cite as

Fluoroimidazoles and their Heteroannelated Derivatives: Synthesis and Properties (Review)

  • G. N. Lipunova
  • E. V. Nosova
  • V. N. Charushin
Article

Published data on methods of synthesis, chemical properties, and biological activity of fluoroimidazoles and their heteroannelated derivatives are summarized and classified.

Keywords

fluoroimidazoles annelation biological activity cycloaddition nucleophilic substitution photoisomerization 

References

  1. 1.
    E. V. Nosova, G. N. Lipunova, and V. N. Charushin, Fluorine-Containing Azines and Benzazines [in Russian], Ural Branch, Russian Academy of Sciences, Yekaterinburg (2011), 456 pp.Google Scholar
  2. 2.
    P. Bouchet, C. Coquelet, and J. Elguero, Bull. Soc. Chim. Fr., 171 (1977).Google Scholar
  3. 3.
    M. J. Silvester, Aldrichimica Acta, 24, 29 (1991).Google Scholar
  4. 4.
    E. V. Aleksandrova, A. N. Kravchenko, and P. M. Kochergin, Khim. Geterotsikl. Soedin., 1603 (2010). [Chem. Heterocycl. Compd., 46, 1295 (2010).]Google Scholar
  5. 5.
    E. V. Aleksandrova, A. N. Kravchenko, and P. M. Kochergin, Khim. Geterotsikl. Soedin., 323 (2011). [Chem. Heterocycl. Compd., 47, 261 (2011).]Google Scholar
  6. 6.
    K. Takahashi, K. L. Kirk, and L. A. Cohen, J. Org. Chem., 49, 1951 (1984).CrossRefGoogle Scholar
  7. 7.
    T. Brown, G. Shaw, and G. J. Durant, J. Chem. Soc., Perkin Trans 1, 2310 (1980).Google Scholar
  8. 8.
    J. Hajduch, C. Cramer, and K. L. Kirk, J. Fluorine Chem., 129, 807 (2008).CrossRefGoogle Scholar
  9. 9.
    J. Heredia-Moya and K. L. Kirk, J. Fluorine Chem., 128, 674 (2007).CrossRefGoogle Scholar
  10. 10.
    K. L. Kirk, W. Nagai, and L. A. Cohen, J. Am. Chem. Soc., 95, 8389 (1973).CrossRefGoogle Scholar
  11. 11.
    H. Levine-Pinto, B. Bouabdallah, J. L. Morgat, D. Gourdji, and P. Fromageot, Biochem. Biophys. Res. Commun., 103, 1121 (1981).CrossRefGoogle Scholar
  12. 12.
    R. Ottlinger, K. Burger, and H. Goth, Tetrahedron Lett., 19, 5003 (1978).CrossRefGoogle Scholar
  13. 13.
    K. Burger, R. Ottlinger, H. Goth, and J. Firl, Chem. Ber., 115, 2494 (1982).CrossRefGoogle Scholar
  14. 14.
    K. Burger, K. Geith, and D. Hübl, Synthesis, 189 (1988).Google Scholar
  15. 15.
    K. Burger, K. Geith, and D. Hübl, Synthesis, 199 (1988).Google Scholar
  16. 16.
    K. Burger, H. Geith, and N. Sewald, J. Fluorine Chem., 46, 105 (1990).CrossRefGoogle Scholar
  17. 17.
    H. H. Karsch, F. Bienlein, and O. Gelmann, Z. Naturforsch., 50, 289 (1995).Google Scholar
  18. 18.
    H. H. Karsch, F. Bienlein, A. Sladek, M. Heckel, and K. Burger, J. Am. Chem. Soc., 117, 5160 (1995).CrossRefGoogle Scholar
  19. 19.
    Z. Jiang, T. Ni, C. Wei, S. Tian, Y. Li, L. Dai, H. Liu, and D. Zhang, Synlett, 24, 215 (2013).CrossRefGoogle Scholar
  20. 20.
    N. Kuhn, H. Bohnen, J. Fahl, D. Blaser, and R. Boese, Chem. Ber., 129, 1579 (1996).CrossRefGoogle Scholar
  21. 21.
    M. El Borai, A. H. Moustafa, M. Anwar, and F. I. Abdel Hay, Pol. J. Chem., 55, 1659 (1981).Google Scholar
  22. 22.
    G. Pawelke, H. Borger, D. J. Brauer, and J. Wilke, J. Fluorine Chem., 36, 185 (1987).CrossRefGoogle Scholar
  23. 23.
    H. Hidetoshi, S. Hiroshi, G. Kenichi, F. Takanori, N. Junko, and N. Teruyuki, JP Pat. Appl. 053650.Google Scholar
  24. 24.
    H. Hidetoshi, S. Hiroshi, F. Takanori, and K. Masahiko, JP Pat. Appl. 275160.Google Scholar
  25. 25.
    O. Mitsuki, N. Shiro, S. Ryoichi, and A. Naoki, JP Pat. Appl. 284711.Google Scholar
  26. 26.
    N. Shiro, O. Mitsuki, S. Ryoichi, and A. Naoki, JP Pat. Appl. 322156.Google Scholar
  27. 27.
    R. P. Subrayan and P. G. Rasmussen, Tetrahedron, 51, 6167 (1995).CrossRefGoogle Scholar
  28. 28.
    M. R. Bryce, R. D. Chambers, S. T. Mullins, and A. Parkin, Bull. Soc. Chim. Fr., 930 (1986).Google Scholar
  29. 29.
    H. Y. Li, I. De Lucca, S. Drummond, and G. A. Boswell, J. Org. Chem., 62, 2550 (1997).CrossRefGoogle Scholar
  30. 30.
    J. W. Pavlik and E. M. Kurzweil, J. Org. Chem., 56, 6313 (1991).CrossRefGoogle Scholar
  31. 31.
    A. M. Ravbaldi and G. Locatalli, Eur. J. Med. Chem., 29, 339 (1994).CrossRefGoogle Scholar
  32. 32.
    S. Langer, S. Arbilla, J. Benavides, and B. Scatton, Adv. Biochem. Psychopharmacol., 46, 61 (1990).Google Scholar
  33. 33.
    O. J. Sanger and B. Zivkovic, Psychopharmacol., 89, 317 (1986).Google Scholar
  34. 34.
    F. Huq, H. Daghriri, J. Q. Yu, P. Beale, and K. Fisher, Eur. J. Med. Chem., 39, 691 (2004).CrossRefGoogle Scholar
  35. 35.
    F. Zeng, J. A. Southerland, R. J. Voll, J. R. Votaw, L. Williams, B. J. Ciliax, A. I. Levey, and M. M. Goodman, Bioorg. Med. Chem. Lett., 16, 3015 (2006).CrossRefGoogle Scholar
  36. 36.
    F. Shibahara, E. Yamaguchi, A. Kitagawa, A. Imai, and T. Murai, Tetrahedron, 65, 5062 (2009).CrossRefGoogle Scholar
  37. 37.
    V. B. Sokolov, A. Yu. Aksinenko, and I. V. Martynov, Izv. Akad. Nauk, Ser. Khim., 460 (2005). [Russ. Chem. Bull., 54, 470 (2005).]Google Scholar
  38. 38.
    A. N. Levov, V. B. Sokolov, A. Yu. Aksinenko, A. V. Il'ina, and V. P. Varlamov, Zh. Obshch. Khim., 81, 1005 (2011). [Russ. J. Gen. Chem., 81, 1198 (2011).]Google Scholar
  39. 39.
    V. B. Sokolov, A. Yu. Aksinenko, T. A. Epishina, and T. V. Goreva, Izv. Akad. Nauk, Ser. Khim., 614 (2009). [Russ. Chem. Bull., 58, 631 (2009).]Google Scholar
  40. 40.
    V. B. Sokolov and A. Yu. Aksinenko, Izv. Akad. Nauk, Ser. Khim., 1433 (2009). [Russ. Chem. Bull., 58, 1476 (2009).]Google Scholar
  41. 41.
    Y. V. Rassukana, Y. Y. Khomutnyk, P. P. Onys‘ko, A. D. Sinitsa, and A. A. Gakh, J. Fluorine Chem., 131, 1044 (2010).CrossRefGoogle Scholar
  42. 42.
    A. Yu. Aksinenko, T. V. Goreva, T. A. Epishina, and V. B. Sokolov, J. Fluorine Chem., 137, 105 (2012).CrossRefGoogle Scholar
  43. 43.
    Y. Y. Khomutnyk, Y. V. Rassukana, P. P. Onys’ko, and A. D. Synytsya, Phosphorus, Sulfur Silicon Relat. Elem., 188, 179 (2013).CrossRefGoogle Scholar
  44. 44.
    M. Kurzepa, J. Cz. Dobrowolski, and A. P. Mazurek, J. Mol. Struct., 565-566, 107 (2001).CrossRefGoogle Scholar
  45. 45.
    G. Galley, Z. K. Groebke, R. Norcross, and H. Stalder, WO Pat. Appl. 2008058867.Google Scholar
  46. 46.
    J. Fan, B. Dolensky, I. H. Kim, and K. L. Kirk, J. Fluorine Chem., 115, 137 (2002).CrossRefGoogle Scholar
  47. 47.
    G. Alvaro, D. Amantini, E. Castiglioni, R. Di Fabio, and F. Pavone, US Pat. Appl. 20100144760.Google Scholar
  48. 48.
    F. Jung and G. M. Davies, US Pat. Appl. 4486426.Google Scholar
  49. 49.
    F. H. Jung, US Pat. Appl. 4463173.Google Scholar
  50. 50.
    A. J. Barker and C. Johnstone, US Pat. Appl. 5866572.Google Scholar
  51. 51.
    J. Geiwiz, E. Goetschi, P. Hebeisen, H. Link, and T. Luebbers, US Pat. Appl. 5589473.Google Scholar
  52. 52.
    R. A. Kunetskiy, S. M. Polyakova, J. Vavrik, I. Cisarova, J. Saame, E. R. Nerut, I. Koppel, A. Kutt, I. Leito, and I. M. Lyapkalo, Chem.–Eur. J., 18, 3621 (2012).CrossRefGoogle Scholar
  53. 53.
    Y. Takeuchi, K. L. Kirk, and L. A. Cohen, J. Org. Chem., 44, 4243 (1979).CrossRefGoogle Scholar
  54. 54.
    E. C. Coad, J. Kampf, and P. G. Rasmussen, J. Org. Chem., 61, 6666 (1996).CrossRefGoogle Scholar
  55. 55.
    K. Burger, D. Hübl, and K. Geith, Synthesis, 194 (1988).Google Scholar
  56. 56.
    K. Burger, E. Hoess, and K. Geith, Synthesis, 360 (1990).Google Scholar
  57. 57.
    R. A. Egolf and D. M. Bilder, J. Heterocycl. Chem., 31, 541 (1994).CrossRefGoogle Scholar
  58. 58.
    Y. Hayakawa, H. Kimoto, L. A. Cohen, and K. L. Kirk, J. Org. Chem., 63, 9448 (1998).CrossRefGoogle Scholar
  59. 59.
    J. A. Finkelstein, R. M. Keenan, and J. Weinstock, US Pat. Appl. 5185351.Google Scholar
  60. 60.
    J. Finkelstein, J. Hempel, R. M. Keenan, J. Samanen, and J. Weinstock, US Pat. Appl. 5234917.Google Scholar
  61. 61.
    G. P. Luke, G. Maynard, S. Mitchell, A. Thurkauf, L. Xie, L. Zhang, S. Zhang, H. Zhao, B. Chenard, Y. Gao, B. Han, and X. S. He, WO Pat. Appl. 03082829.Google Scholar
  62. 62.
    C. Thibeault, P. J. Edwards, C. Kuhn, B. Moreau, M. Poirier, and S. Surprenant, WO Pat. Appl. 2012048421.Google Scholar
  63. 63.
    H. Zhang, L. Zhou, F. Amblard, J. Shi, D. R. Bobeck, S. Tao, T. R. McBrayer, P. M. Tharnish, T. Whitaker, S. J. Coats, and R. F. Schinazi, Bioorg. Med. Chem. Lett., 22, 4864 (2012).CrossRefGoogle Scholar
  64. 64.
    C. A. Coburn, H. Wu, B. Hu, B. Zhong, D. Wang, Z. Xu, F. Sun, T. Ji, and Z. Dan, WO Pat. Appl. 2012003642.Google Scholar
  65. 65.
    B. W. Metcalf and M. Jung, US Pat. Appl. 4100349.Google Scholar
  66. 66.
    B. W. Metcalf and M. Jung, US Pat. Appl. 4103089.Google Scholar
  67. 67.
    N. Machinaga, J. Chiba, F. Muro, H. Yuita, and J. Watanabe, WO Pat. Appl. 2011102404.Google Scholar
  68. 68.
    C. S. Burgey, Z. J. Deng, D. N. Nguyen, D. V. Paone, C. M. Potteiger, S. R. Stauffer, C. Segerdell, A. Nomland, and J. J. Lim, WO Pat. Appl. 2010111058.Google Scholar
  69. 69.
    B. B. Busch, B. T. Flatt, X. H. Gu, S. P. Lu, R. Martin, R. Mohan, M. C. Nyman, E. Schweiger, W. C. Stevens, Jr., T. L. Wang, and Y. Xie, WO Pat. Appl. 2007002563.Google Scholar
  70. 70.
    R. M. Keenan and J. Weinstock, EP Pat. Appl. 0425211.Google Scholar
  71. 71.
    W. C. Pringle, J. M. Peterson, L. Xie, P. Ge, Y. Gao, J. W. Ochterski, and J. Lan, US Pat. Appl. 2010297035.Google Scholar
  72. 72.
    V. M. Labroo, K. L. Kirk, L. A. Cohen, D. Delbeke, and P. S. Dannies, Biochem. Biophys. Res. Commun., 113, 581 (1983).CrossRefGoogle Scholar
  73. 73.
    G. Feuerstein, D. Lozovsky, L. A. Cohen, V. M. Labroo, K. L. Kirk, I. J. Kopin, and A. I. Faden, Neuropeptides, 4, 303 (1984).CrossRefGoogle Scholar
  74. 74.
    S. Vonhof, I. Paakkari, G. Feuerstein, L. A. Cohen, and V. M. Labroo, Eur. J. Pharmacol., 164, 77 (1989).CrossRefGoogle Scholar
  75. 75.
    T. Chandra, X. Zou, E. J. Valente, and K. L. Brown, J. Org. Chem., 71, 5000 (2006).CrossRefGoogle Scholar
  76. 76.
    P. Pevarello, A. M. Garcia Collazo, and A. B. Garcia Garcia, WO Pat. Appl. 2009040552.Google Scholar
  77. 77.
    P. Pevarello, A. M. Garcia Collazo, H. A. Rodriguez, C.-G. P. Saluste, F. J. Ramos Lima, C. E. Gonzalez, and S. J. Oyarzabal, WO Pat. Appl. 2009060197.Google Scholar
  78. 78.
    W. Vaccaro, Z. Chen, D. S. Dodd, T. N. Huynh, J. Lin, C. Liu, C. P. Mussari, J. Tokarski, D. R. Tortolani, and S. T. Wrobleski, US Pat. Appl. 2007078136.Google Scholar
  79. 79.
    M. Vennemann, T. Maier, S. Hoelder, G. Beneke, F. Dehmel, A. Zuelch, A. Strub, T. Beckers, S. Ince, H. Rehwinkel, N. Liu, and U. Boemer, WO Pat. Appl. 2010091808.Google Scholar
  80. 80.
    N. Miyamoto, S. Matsumoto, and S. Imamura, WO Pat. Appl. 2009136663.Google Scholar
  81. 81.
    K. Bando and K. Taguchi, WO Pat. Appl. 2007063946.Google Scholar
  82. 82.
    J. L. Duffy, S. D. Edmondson, D. Kim, B. A. Kirk, L. Wang, and A. E. Weber, WO Pat. Appl. 2004058266.Google Scholar
  83. 83.
    M. Gianotti, C. Corti, S. Delle Fratte, R. Di Fabio, C. P. Leslie, F. Pavone, L. Piccoli, L. Stasi, and M. J. Wigglesworth, Bioorg. Med. Chem. Lett., 20, 5069 (2010).CrossRefGoogle Scholar
  84. 84.
    R. Di Fabio, M. Gianotti, C. P. Leslie, and L. P. Stasi, WO Pat. Appl. 2010142652.Google Scholar
  85. 85.
    S. Hoelder, M. Vennemann, G. Beneke, A. Zuelch, V. Gekeler, T. Beckers, A. Zimmermann, and H. Joshi, WO Pat. Appl. 2009021992.Google Scholar
  86. 86.
    G. Alvaro, D. Amantini, and S. Belvedere, US Pat. Appl. 2009022670.Google Scholar
  87. 87.
    Y. Kano, T. Sasaki, Y. Sambongi, K. Tanabe, Y. Akiyama, H. Kitagawa, T. Maruyama, H. Takizawa, T. Ando, K. Aihara, K. Atsumi, K. Iwamatsu, and T. Ida, US Pat. Appl. 6458780.Google Scholar
  88. 88.
    R. Dumeunier, C. Lamberth, S. Trah, and S. Wendeborn, WO Pat. Appl. 2009053102.Google Scholar
  89. 89.
    Y. Tanaka, Y. Kajiwara, M. Noguchi, T. Kajiwara, and T. Tabuchi, PT Pat. Appl. 1466527.Google Scholar
  90. 90.
    W. Q. Deng, V. Molinero, and W. A. Goddard III, J. Am. Chem. Soc., 126, 15644 (2004).CrossRefGoogle Scholar
  91. 91.
    N. Nagakura, JP Pat. Appl. 2005112733.Google Scholar
  92. 92.
    Y. Nakayama, K. Hiyama, and T. Iwasaki, WO Pat. Appl. 2010001830.Google Scholar
  93. 93.
    S. Takada, JP Pat. Appl. 4474492.Google Scholar
  94. 94.
    K. K. Laali, M. Tanaka, F. Forohar, M. Cheng, and J. C. Fetzer, J. Fluorine Chem., 91, 185 (1998).CrossRefGoogle Scholar
  95. 95.
    P. Tang, W. Wang, and T. Ritter, J. Am. Chem. Soc., 133, 11482 (2011).CrossRefGoogle Scholar

Copyright information

© Springer Science+Business Media New York 2014

Authors and Affiliations

  • G. N. Lipunova
    • 1
  • E. V. Nosova
    • 2
  • V. N. Charushin
    • 1
    • 2
  1. 1.I. Ya. Postovskii Institute of Organic Chemistry, Urals BranchRussian Academy of SciencesYekaterinburgRussia
  2. 2.Ural Federal University named after the First President of Russia B. N. YeltsinYekaterinburgRussia

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