Skip to main content
SpringerLink
Log in

Properties of haloimidazoles (review)

  • Published:
Chemistry of Heterocyclic Compounds Aims and scope

Published data on the chemical and physicochemical properties of haloimidazoles are reviewed and classified.

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. E. V. Aleksandrova, A. N. Kravchenko, and P. M. Kochergin, Khim. Geterotsikl. Soedin., 1603 (2010). [Chem. Heterocycl. Comp., 46, 1295 (2010)].

    Article  Google Scholar 

  2. E. C. Coard, Liu Hui, and P. G. Rasmussen, Tetrahedron, 55, 2811 (1999).

    Article  Google Scholar 

  3. H. J. C. Yeh, K. L. Kirk, L. A. Cohen, and J. S. Cohen, J. Chem. Soc., Perkin Trans. 2, 928 (1975).

  4. J. E. Oliver and E. B. Stokes, J. Heterocycl. Chem., 7, 961 (1970).

    Article  CAS  Google Scholar 

  5. B. Nagaraj, T. Narasimhamurthy, H. S. Yathirajan, P. Nagaraja, R. S. Narasegowda, and R. S. Rathore, Acta Crystallogr., C61, 177 (2005).

    Google Scholar 

  6. H. S. Yathirajan, B. Nagaraj, R. S. Narasegowda, P. Nagaraja, and M. Bolte, Acta Crystallogr., E61, 1193 (2005).

    Google Scholar 

  7. H. S. Yathirajan, C. R. Raju, K. M. Rai, K. Jailakshmi, P. Nagaraja, K. Palani, M. N. Ponnuswamy, and M. Nethaji, J. Chem. Cristallogr., 35, 211 (2005).

    Article  CAS  Google Scholar 

  8. J. Garcia and J. Villarasa, Heterocycles, 27, 803 (1988).

    Google Scholar 

  9. A. N. Nesmeyanov, D. N. Kravtsov, A. P. Zhukov, P. M. Kochergin, and G. K. Semin, Dokl. Akad. Nauk SSSR, 179, 102 (1968).

    CAS  Google Scholar 

  10. M. L. S. Garcia, J. A. S. Smith, P. M. G. Bavin, and C. R. Genellin, J. Chem. Soc., Perkin Trans. 2, 1391 (1983).

  11. I. Suwinski and E. Salwinska, Pol. J. Chem., 55, 2525 (1981).

    CAS  Google Scholar 

  12. Y. Takeuchi, K. L. Kirk, and L. A. Cohen, J. Org. Chem., 43, 3570 (1978).

    Article  CAS  Google Scholar 

  13. Y. Takeuchi, K. L. Kirk, and L. A. Cohen, J. Org. Chem., 44, 4240 (1979).

    Article  CAS  Google Scholar 

  14. H. B. Bensusan and M. S. R. Naidu, Biochemistry, 6, 12 (1967).

    Article  CAS  Google Scholar 

  15. M. S. R. Naidu and H. B. Bensusan, J. Org. Chem., 33, 1307 (1968).

    Article  Google Scholar 

  16. M. E. Borai, A. N. Moustafa, M. Anwar, and F. I. Abdel Hay, Pol. J. Chem., 55, 1659 (1981).

    Google Scholar 

  17. A. R. Katritzky, I. I. Slavinsky, and F. Brunner, J. Chem. Soc., Perkin Trans. 1, 1139 (1989).

  18. P. M. Kochergin, Khim. Geterotsikl. Soedin., 402 (1965). [Chem. Heterocycl. Comp., 1, 268 (1965)].

    Article  Google Scholar 

  19. G. L. Schmir and L. A. Cohen, Biochemistry, 4, 533 (1965).

    Article  CAS  Google Scholar 

  20. M. P. Groziak and L. Wei, J. Org. Chem., 56, 4296 (1991).

    Article  CAS  Google Scholar 

  21. G. E. Trout and P. R. Levy, Recl. Trav. Chim. Pays-Bas, 84, 1257 (1965).

    Article  CAS  Google Scholar 

  22. G. E. Trout and P. R. Levy, Recl. Trav. Chim. Pays-Bas, 85, 765 (1966).

    Article  CAS  Google Scholar 

  23. P. M. Kochergin and I. S. Mikhailova, USSR Inventor's Certificate 225201; Byul. Izobr., No. 27, 20 (1968).

    Google Scholar 

  24. P. M. Kochergin, M. A. Klykov, and I. S. Mikhailova, Khim. Geterotsikl. Soedin., 820 (1972). [Chem. Heterocycl. Comp., 8, 742 (1972)].

    Article  Google Scholar 

  25. M. A. Klykov, Author’s Thesis Cand. Chem. Sci. [in Russian], Moscow (1982).

  26. M. S. Shvartsberg, L. N. Bizhan, A. N. Sinyakov, and N. R. Myasnikov, Izv. Akad. Nauk SSSR, Ser. Khim., 1563 (1979).

  27. W. E. Allen, Ch. J. Fowler, V. M. Lynch, and J. L. Sessler, Chem. Eur. J., 7, 721 (2001).

    Article  CAS  Google Scholar 

  28. B. Iddon and N. Khan, Tetrahedron Lett., 27, 1635 (1986).

    Article  CAS  Google Scholar 

  29. B. Iddon and N. Khan, J. Chem. Soc., Perkin Trans. 1, 1445 (1987).

  30. B. Iddon, N. Khan, and B. L. Lim, J. Chem. Soc., Perkin Trans. 1, 1437 (1987).

  31. B. Iddon, N. Khan, and B. L. Lim, J. Chem. Soc., Chem. Commun., 1428 (1985).

  32. B. Iddon and N. Khan, J. Chem. Soc., Perkin Trans. 1, 1453 (1987).

  33. E. V. Aleksandrova and P. M. Kochergin, Khim. Farm. Zh., 44, No. 7, 34 (2010).

    Google Scholar 

  34. A. W. Lutz and S. Delorenzo, J. Heterocycl. Chem., 4, 399 (1967).

    Article  CAS  Google Scholar 

  35. M. S. Shvartsberg, L. N. Bizhan, and I. L. Kotlyarevskii, Izv. Akad. Nauk SSSR, Ser. Khim., 1534 (1971).

  36. F. Farba, C. Galvez, A. Goncalez, P. Viladoms, and J. Vilarrasa, J. Heterocycl. Chem., 15, 1227 (1978).

    Article  Google Scholar 

  37. J. D. Albright and D. R. Moran, J. Heterocycl. Chem., 23, 913 (1986).

    Article  CAS  Google Scholar 

  38. Boots Pure Drug Co. Ltd., Netherlands Pat. Appl. 660959; Chem. Abstr., 67, 643986 (1967).

    Google Scholar 

  39. B. Laksmi, H. P. Ramiya, D. J. Plata, S. A. King, and E. Morton-Howard, Heterocycles, 53, 729 (2000).

    Article  Google Scholar 

  40. T. Chandra, X. Zou, E. J. Valente, and K. L. Brown, J. Org. Chem., 71, 5000 (2006).

    Article  CAS  Google Scholar 

  41. H. Wamhoff, W. Kleimann, G. Kunz, and C. H. Theis, Angew. Chem., Int. Ed., 20, 612 (1981).

    Article  Google Scholar 

  42. K. L. Kirk and L. A. Cohen, J. Am. Chem. Soc., 93, 3060 (1971).

    Article  CAS  Google Scholar 

  43. M. Hoffer, V. Toome, and A. Brossi, J. Heterocycl. Chem., 3, 454 (1966).

    Article  CAS  Google Scholar 

  44. C. P. Whittle, Aust. J. Chem., 33, 1545 (1980).

    Article  CAS  Google Scholar 

  45. M. Moreno-Manas, J. Bassa, N. Liado, and R. J. Pleixtats, J. Heterocycl. Chem., 27, 673 (1990).

    Article  CAS  Google Scholar 

  46. M. A. Clyne and F. Aldabbagh, Org. Biomol. Chem., 4, 268 (2006).

    Article  CAS  Google Scholar 

  47. R. M. de Figueiredo, S. Thoret, C. Huet, and J. Dubois, Synthesis, 529 (2007).

  48. P. M. Kochergin, B. A. Priimenko, V. S. Ponomar’, M. V. Povstyanoi, A. A. Tkachenko, I. A. Mazur, A. N. Krasovskii, E. G. Khysh, and M. I. Yurchenko, Khim. Geterotsikl. Soedin., 177 (1969). [Chem. Heterocycl. Comp., 5, 135 (1969)].

    Article  Google Scholar 

  49. B. A. Priimenko, Khim. Geterotsikl. Soedin., 1243 (1971). [Chem. Heterocycl. Comp., 7, 1168 (1971)].

    Article  Google Scholar 

  50. I. A. Mazur, P. M. Kochergin, and G. S. Tkachenko, Khim. Geterotsikl. Soedin., 824 (1970). [Chem. Heterocycl. Comp., 6, 763 (1970)].

    Article  Google Scholar 

  51. P. M. Kochergin, B. A. Priimenko, V. S. Ponomar’, M. V. Povstyanoi, A. A. Tkachenko, I. A. Mazur, A. N. Krasovskii, E. G. Knysh, and M. I. Yurchenko, Khim. Geterotsikl. Soedin., 129 (1970). [Chem. Heterocycl. Comp., 6, 125 (1970)].

    Article  Google Scholar 

  52. B. A. Priimenko and P. M. Kochergin, Khim. Geterotsikl. Soedin., 1252 (1971). [Chem. Heterocycl. Comp., 7, 1177 (1971)].

    Article  Google Scholar 

  53. K. L. Kirk, J. Heterocycl. Chem., 22, 57 (1985).

    Article  CAS  Google Scholar 

  54. K. E. Stensio, K. Wahlberg, and R. Wahren, Acta Chem. Scand., 27, 2179 (1973).

    Article  CAS  Google Scholar 

  55. H. Rutz and K. Gubler, Pat. SAR 6802643; Chem. Abstr., 71, 38964 (1969).

  56. G. Pissiotas, Ger. Offen. No. 2031400; Chem. Abstr., 74, 100059 (1971).

  57. J. C. Reepmeyer, K. L. Kirk, and L. A. Cohen, Tetrahedron Lett., 4107 (1975).

  58. M. Fuentes, S. R. Naik, R. K. Robins, and J. T. Witkowsky, in: Res. Commun. V Intern. Congr. Chem. Heterocycles, Lublana, Yugoslavia, 1975, c. 348.

  59. P. M. Kochergin, Khim. Geterotsikl. Soedin., 754 (1965). [Chem. Heterocycl. Comp., 1, 511 (1965)].

    Article  Google Scholar 

  60. K. Shimada, J. Pharm. Soc. Jpn., 91, 221 (1971).

    CAS  Google Scholar 

  61. D. S. Noyce and G. T. Stowe, J. Org. Chem., 38, 3762 (1973).

    Article  CAS  Google Scholar 

  62. J. Permak, A. Skrzypczak, and J. Krysinsky, Pharmazie, 38, 752 (1983).

    Google Scholar 

  63. J. Howarth, J.-L. Thomas, K. Hanlon, and D. McGuirk, Synth. Commun., 30, 1865 (2000); Chem. Abstr., 133, 43605 (2000).

    Google Scholar 

  64. K. L. Kirk, J. Org. Chem., 43, 4381 (1978).

    Article  CAS  Google Scholar 

  65. M. S. Neelakandha, J. A. Jablonowski, and J. K. Todd, J. Org. Chem., 69, 8115 (2004).

    Article  Google Scholar 

  66. B. D. Palmer and W. A. Denny, J. Chem. Soc., Perkin Trans. 1, 95 (1989).

  67. B. Iddon, Heterocycles, 23, 417 (1985).

    Article  CAS  Google Scholar 

  68. V. S. Mokrushin, V. I. Nifontov, Z. V. Pushkareva, and V. I. Ofitserov, Khim. Geterotsikl. Soedin., 1421 (1971). [Chem. Heterocycl. Comp., 7, 1326 (1971)].

    Article  Google Scholar 

  69. D. A. De Bie and H. C. Van Der Plas, Recl. Trav. Chim. Pays-Bas, 88, 1246 (1969).

    Article  Google Scholar 

  70. T. Kauffmann, R. Nurnberg, J. Schulz, R. Stabba, and X. Hetarine, Tetrahedron Lett., 4273 (1967).

  71. D. A. De Bie, H. C. Van Der Plas, and G. Geurtsen, Recl. Trav. Chim. Pays-Bas, 90, 594 (1971).

    Google Scholar 

  72. F. Bellina, S. Cauteruccio, and R. Rossi, J. Org. Chem., 72, 8543 (2007).

    Article  CAS  Google Scholar 

  73. M. R. Bhandari, R. Sivappa, and C. J. Lovely, Org. Lett., 11, 1535 (2009).

    Article  CAS  Google Scholar 

  74. E. V. Aleksandrova, A. N. Kravchenko, and P. M. Kochergin, Khim. Geterotsikl. Soedin., 3 (2010). [Chem. Heterocycl. Comp., 46, 1 (2010)].

    Article  CAS  Google Scholar 

  75. K. Burger, R. Ottinger, H. Goth, J. Firl, Chem. Ber., 115, 2494 (1982).

    Article  CAS  Google Scholar 

  76. R. V. Khozeva, I. Ya. Kvitko, A. V. El’tsov, E. L. Baranov, USSR Inventor’s Certificate No. 525676 (1976); Chem. Abstr., 86, 89818 (1977).

  77. R. V. Khozeva, I. Ya. Kvitko, E. L. Baranov, and A. V. El'tsov. Zh. Org. Khim., 13, 232 (1977).

    Google Scholar 

  78. B. Iddon, N. Khan, B. L. Lim, and J. Chem. Soc., Perkin Trans. 1, 1457 (1987).

  79. H.-T. Wang, Y.-Y. Song, M. Y. Chiang, and W.-F. Zeng, Acta Cristallogr., E62, 2464 (2006).

    Google Scholar 

  80. K. L. Kirk, W. Nagai, and L. A. Cohen, J. Am. Chem. Soc., 95, 8389 (1973).

    Article  CAS  Google Scholar 

  81. B. A. Priimenko and P. M. Kochergin, Khim. Geterotsikl. Soedin., 1248 (1971). [Chem. Heterocycl. Comp., 7, 1173 (1971)].

    Article  Google Scholar 

  82. W. Nagai, K. L. Kirk, and L. A. Cohen, J. Org. Chem., 38, 1971 (1973).

    Article  CAS  Google Scholar 

  83. K. Zauer-Csüllog and K. Lempert, Chem. Ber., 106, 1628 (1973).

    Article  Google Scholar 

  84. A. Tranti and E. Bellasio, J. Heterocycl. Chem., 11, 257 (1974).

    Article  Google Scholar 

  85. F. Saczewski, M. Gdaniec, and K. Osmiatowski, J. Chem. Soc., Perkin Trans. 1, 1033 (1987).

  86. G. I. Gofen, Ch. Sh. Kadyrov, and M. N. Kosyakovskaya, Khim. Geterotsikl. Soedin., 282 (1971). [Chem. Heterocycl. Comp., 7, 261 (1971)].

    Article  Google Scholar 

  87. E. R. Lavagnino and D. C. Thompson, J. Heterocycl. Chem., 9, 149 (1972).

    Article  CAS  Google Scholar 

  88. M. S. Shvartsberg, L. N. Bizhan, E. E. Zaev, and I. L. Kotlyarevskii, Izv. Akad. Nauk SSSR, Ser. Khim., 1472 (1972).

  89. L. N. Bizhan, P. A. Slabuka, A. R. Kolpakov, O. R. Grek, E. G. Izyumov, M. S. Shvartsberg, and I. L. Kotlyarevskii, Izv. Akad. Nauk SSSR, Ser. Khim., 2638 (1973).

  90. J. Kerherve, C. Botuha, and J. Dubois, Org. Biomol. Chem., 7, 2214 (2009).

    Article  CAS  Google Scholar 

  91. A. K. Nadipuram, W. M. David, D. Kumar, and S. M. Kerwin, Org. Lett., 4, 4545 (2002).

    Article  Google Scholar 

  92. T. Sakamoto, H. Nagata, Y. Kondo, M. Shiraiwa, and H. Yamanaka, Chem. Pharm. Bull., 35, 823 (1987).

    CAS  Google Scholar 

  93. D. A. Evans and T. Bach, Angew. Chem., Int. Ed., 32, 1326 (1993).

    Article  Google Scholar 

  94. M. R. Eberhard, Org. Lett., 6, 2125 (2004).

    Article  CAS  Google Scholar 

  95. S. B. Prasad, T. M. Stevenson, J. R. Citineni, V. Nysam, and P. Knochel, Tetrahedron, 53, 7237 (2004).

    Article  Google Scholar 

  96. R. F. M. Schnürch, A. F. Khan, M. Spina, M. D. Mihovilovic, and P. Stanetty, Eur. J. Org. Chem., 3283 (2006).

  97. P. J. Garegg and B. Samuelsson, Synthesis, 469 (1979).

  98. P. J. Garegg and B. Samuelsson, Synthesis, 813 (1979).

  99. P. J. Garegg and B. Samuelsson, J. Chem. Soc., Chem. Commun., 978 (1979).

  100. P. J. Garegg and B. Samuelsson, J. Chem. Soc., Perkin Trans. 1, 2866 (1980).

  101. P. J. Garegg and B. Samuelsson, Can. J. Chem., 59, 339 (1981).

    Article  Google Scholar 

  102. P. J. Garegg, R. Johnson, C. Ortega, and B. Samuelsson, J. Chem. Soc., Perkin Trans. 1, 681 (1982).

  103. M. D. Mashkovskii, Drugs [in Russian], Novaya Volna, Moscow (2005), p. 444.

    Google Scholar 

  104. C. Almansa, J. Bartroli, J. Billoc, F. L. Cavalcanti, R. Ferrando, L. A. Gomez, I. Ramis, E. Carieller, M. Merlos, and J. Garcia-Rafanell, J. Med. Chem., 47, 5579 (2004).

    Article  CAS  Google Scholar 

  105. C. Almansa, J. Alfon, A. F. de Arriba, F. L. Cavalcanti, I. Escamilla, L. A. Gomez, A. Miralles, R. Soliva, J. Bartroli, E. Carceller, M. Merlos, and J. Garcia-Rafanell, J. Med. Chem., 46, 3463 (2003).

    Article  CAS  Google Scholar 

  106. C. S. A. Kumar, S. N. Swamy, S. L. Gaonkar, Basappa, B. P. Salimath, and K. S. Rangappa, Med. Chem., 3, 269 (2007).

    Article  CAS  Google Scholar 

  107. R. D. Verscheyle, A. W. Brown, and C. A. Tompson, Arch. Toxicol., 56, 109 (1984).

    Article  Google Scholar 

  108. H. Yamaga, H. Yamaguchi, K. Maruta, M. Yasuchi, F. Hirota, and J. Ichihara. Jpn. Pat. 109467; Chem. Abstr., 132, 279218 (2000).

    Google Scholar 

  109. G. Courtemanche, O. Crespin, and C. Pascal, PCT Int. Appl. WO 0164631; Chem. Abstr., 135, 226993 (2001).

  110. P. R. Bovy, G. Courtemanche, and O. Crespin, PCT Int. Appl. WO 0164671; Chem. Abstr., 135, 226994 (2001).

    Google Scholar 

  111. R. Soliva, C. Almansa, S. J. Kalko, F. J. Luque, and M. Orosco, J. Med. Chem., 46, 1372 (2003).

    Article  CAS  Google Scholar 

  112. B. Schmidt and B. Schieffer, J. Med. Chem., 46, 2262 (2003).

    Google Scholar 

  113. J. Zamora, L. Afzelius, and G. Cruciani, J. Med. Chem., 46, 2313 (2003).

    Article  CAS  Google Scholar 

  114. M. Amini, A. Foroumadi, M. Vosooghi, H. R. Vahdatizadeh, and A. Shafiee, Asian J. Chem., 19, 4679 (2007).

    CAS  Google Scholar 

  115. K. L. Kirk and L. A. Cohen, J. Am. Chem. Soc., 95, 4619 (1973).

    Article  CAS  Google Scholar 

  116. K. L. Kirk, L. A. Cohen, Symp. Am. Chem. Soc., 28, 23 (1976).

    CAS  Google Scholar 

  117. C. B. Klee, L. E. LaJohn, K. L. Kirk, and L. A. Cohen, Biochem. Biophys. Res. Commun., 75, 674 (1977).

    Article  CAS  Google Scholar 

  118. C. R. Creveling, K. L. Kirk, and B. Highman, Res. Commun. Chem. Pathol. Pharmacol., 16, 507 (1977); Chem. Abstr., 87, 296 (1977).

    Google Scholar 

  119. D. C. Klein, I. L. Weller, K. L. Kirk, and R. W. Hartley, Mol. Pharmacol., 13, 1105 (1977); Chem. Abstr., 88, 32538 (1978).

    Google Scholar 

  120. B. W. Metcalf and M. Jung, Belg. Pat. 868595; Chem. Abstr., 90, 1378196 (1979).

    Google Scholar 

  121. E. De Clercq, A. Billiau, V. G. Edy, K. L. Kirk, and L. A. Cohen, Biochem. Biophys. Res. Commun., 82, 840 (1978); Chem. Abstr., 89, 100939 (1978).

    Google Scholar 

  122. P. F. Torrence, R. M. Friedman, K. L. Kirk, L. A. Cohen, and C. R. Creveling, Biochem. Pharmacol., 28, 2565 (1979); Chem. Abstr., 92, 15242 (1980).

    Google Scholar 

  123. K. L. Kirk, J. Fluor Chem., 127, 1013 (2006).

    Article  CAS  Google Scholar 

  124. B. Heckmann, J.-P. Vevert, and J. Zhang, PCT Int. Appl. WO 9604275; Chem. Abstr., 125, 58527 (1996).

    Google Scholar 

  125. B. Heckmann, J.-P. Vevert, and J. Zhang, PCT Int. Appl. WO 9604276; Chem. Abstr., 125, 33659 (1996).

    Google Scholar 

  126. R. Betageri and R. P. Raymond, PCT Int. Appl. WO 0170703; Chem. Abstr., 135, 272956 (2001).

    Google Scholar 

  127. X. Chen and X. He, US Pat. 6288230; Chem. Abstr., 135, 226996 (2001).

  128. G. Beck, K. Sasse, H. Heitzer, H. Eue, R. Schmidt, and H. Scheinpflug Ger. Offen. 2610527; Chem. Abstr., 88, 6886 (1978).

  129. R. Seele, S. Karbach, H. Sauter, E. Ammermann, G. Lorenz, and N. Götz, Ger. Offen. DE 3825586; Chem. Abstr., 113, 6340 (1990).

    Google Scholar 

  130. M. Ogawa, A. Nishimura, Eur. Pat. 1417887; Ref. Zh. Khim., 04.18-190.271P (2004).

    Google Scholar 

Download references

Author information

Authors and Affiliations

  1. Zaporozhye State Medical University, 26 Mayakovskyi Ave, Zaporozhye, 69035, Ukraine

    E. V. Aleksandrova

  2. N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky Prospect, Moscow, 119991, Russia

    A. N. Kravchenko

  3. Drug Chemistry Center, All-Russian Pharmaceutical Chemistry Scientific Research Institute, 7 Zubovskaya St., Moscow, 119815, Russia

    P. M. Kochergin

Authors
  1. E. V. Aleksandrova
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. A. N. Kravchenko
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. P. M. Kochergin
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to E. V. Aleksandrova.

Additional information

Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 3, pp. 323–356, March, 2011.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Aleksandrova, E.V., Kravchenko, A.N. & Kochergin, P.M. Properties of haloimidazoles (review). Chem Heterocycl Comp 47, 261–289 (2011). https://doi.org/10.1007/s10593-011-0754-8

Download citation

  • Received:

  • Revised:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s10593-011-0754-8

Keywords

Search

Navigation