Skip to main content
SpringerLink
Log in

Organometallic Tetrazole Derivatives: Preparation and Application to Organic Synthesis

  • Review
  • Published:
Russian Journal of Organic Chemistry Aims and scope Submit manuscript

Abstract

The data are integrated and systematized on preparation procedures and application to the organic synthesis of organometallic tetrazole derivatives, including 5-metallated tetrazoles and tetrazoles with a metal-carbon bond in a substituent, and also organotin tetrazoles.

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. Wittenberger, S.J., Org. Prep. Proc., 1994, vol. 26, p. 499.

    CAS  Google Scholar 

  2. Zubarev, V.Yu. and Ostrovskii, V.A., Khim. Geterotsikl. Soedin., 2002, p. 867.

  3. Herr, R.J., Bioorg. Med. Chem. Lett., 2002, vol. 10, p. 3379.

    CAS  Google Scholar 

  4. Koldobskii, G.I. and Kharbash, R.V., Zh. Org. Khim., 2003, vol. 39, p. 489.

    Google Scholar 

  5. Koldobskii, G.I., Grabalek, A., and Esikov, K.A., Zh. Org. Khim., 2004, vol. 40, p. 479.

    Google Scholar 

  6. Ostrovskii, V.A. and Koldobskii, G.I., Ros. Khim. Zh., 1997, vol. 41, no.2, p. 84.

    CAS  Google Scholar 

  7. Ilyushin, M.A., Tselinskii, I.V., and Chernai, A.V., Ros. Khim. Zh., 1997, vol. 41, no.4, p. 81.

    CAS  Google Scholar 

  8. Moderhack, D., J. Prakt. Chem./Chem. Ztg., 1998, vol. 340, p. 687.

    CAS  Google Scholar 

  9. Voitekhovich, C.V., Gaponik, P.H., and Ivashkevich, O.A., Usp. Khim., 2002, vol. 71, p. 819.

    Google Scholar 

  10. Grimmett, M.R. and Iddon, B., Heterocycles, 1995, vol. 41, p. 1525.

    CAS  Google Scholar 

  11. Gaponik, P.H., Grigor'ev, Yu.V., and Karavai, V.P., Metallorg. Khim., 1988, vol. 1, p. 846.

    CAS  Google Scholar 

  12. Grigor'ev, Yu.V. and Gaponik, P.H., Izv. Akad. Nauk Belarusi, Ser. Khim., 1992, no. 1, p. 73.

  13. USSR Inventor's Certificate 1428754; SSSR Byull. Izobr., 1988, no. 37, p. 2.

  14. Gaponik, P.H., Doctoral Sci. (Chem.) Dissertation, Minsk, 2000.

  15. Shvaika, O.P., Korotkikh, H.I., and Aslanov, A.F., Khim. Geterotsikl. Soed., 1992, p. 1155.

  16. Gaponik, P.H., Haumenko, V.H., Grigor'ev, Yu.V., and Madzievskaya, T.A., Vestn. BGU, 1995, p. 9.

  17. Belen'kii, L.I. and Chuvylkin, L.D., Khim. Geterotsikl. Soed., 1996, p. 1535.

  18. Araki, S., Wanibe, Y., Uno, F., Morikawa, A., Yamamoto, K., Chiba, K., Butsugan, Y., Chem. Ber., 1993, vol. 126, p. 1149.

    CAS  Google Scholar 

  19. Jazwinski, J., Staszewska, O., Stefaniak, L., Araki, S., and Webb, G.A., J. Mol. Str., 2000, vol. 523, p. 103.

    CAS  Google Scholar 

  20. Yi, K.Y. and Yoo, S.-E., Tetrahedron Lett., 1995, vol. 36, p. 1679.

    Article  CAS  Google Scholar 

  21. Satoh, Y. and Marcopulos, N., Tetrahedron Lett., 1995, vol. 36, p. 1759.

    CAS  Google Scholar 

  22. Satoh, Y. and Moliterni, J., Synlett., 1998, p. 528.

  23. Bookser, B.C., Kasibhatla, S.R., Appleman, J.R., and Erion, M.D., J. Med. Chem., 2000, vol. 43, p. 1495.

    CAS  Google Scholar 

  24. Bookser, B.C., Tetrahedron Lett., 2000, vol. 41, p. 2805.

    Article  CAS  Google Scholar 

  25. Jenkins, S.M., Wadsworth, H.J., Bromidge, S., Orlek, B.S., Wyman, P.A., Riley, G.J., and Hawkins, J., J. Med. Chem., 1992, vol. 35, p. 2392.

    Article  CAS  Google Scholar 

  26. Lowack, R.H. and Weiss, R., J. Am. Chem. Soc., 1990, vol. 112, p. 333.

    Article  CAS  Google Scholar 

  27. Weiss, R. and Lowack, R.H., Angew. Chem., 1991, vol. 103, p. 1183.

    CAS  Google Scholar 

  28. Fruhauf, H.-W., Chem. Rev., 1997, vol. 97, p. 523.

    Article  Google Scholar 

  29. Kim, Y.-J., Kim, D.-H., Lee, J.-Y., and Lee, S.-W., J. Organometal. Chem., 1997, vol. 538, p. 189.

    Article  CAS  Google Scholar 

  30. Kim, Y.-J., Kwak, Y.-S., and Lee, S.-W., J. Organometal. Chem., 2000, vol. 603, p. 152.

    Article  CAS  Google Scholar 

  31. Kim, Y.-J., Lee, S.-H., Lee, S.-H., Jeon, S.-I., Lim, M.-S., and Lee, S.-W., Inorg. Chim. Acta, 2005, vol. 358, p. 650.

    CAS  Google Scholar 

  32. Kim, Y.-J., Kwak, Y.-S., Joo, Y.-S., and Lee, S.-W., J. Chem. Soc., Dalton Trans., 2002, p. 144.

  33. Kim, Y.-J., Joo, Y.-S., Han, J.-T., Han, W.S., and Lee, S.W., J. Chem. Soc., Dalton Trans., 2002, p. 3611.

  34. Kim, W.S., Kim, Y.-J., and Lee, S.W., Bull. Korean, Chem. Soc., 2002, vol. 23, p. 1177.

    CAS  Google Scholar 

  35. Han, W.S., Li, H.K., Kim, Y.-J., and Lee, S.-W., Acta Cryst. E, 2004, vol. 60, m1813.

    Google Scholar 

  36. Wehlan, M., Thiel, R., Fuchs, J., Beck, W., and Fehlhammer, W.P., J.Organometal. Chem., 2000, vol. 613, p. 159.

    Article  CAS  Google Scholar 

  37. German Patent, 19736150.

  38. Caipa, M.A., Poveda, A., and Perilla, I.C., J. Coord. Chem., 2003, vol. 56, p. 353.

    Article  CAS  Google Scholar 

  39. Moody, C.J., Rees, C.W., and Young, R.G., J. Chem. Soc., Perkin Trans. I, 1991, p. 323.

  40. Thomas, E.W. and Cudahy, M.M., J. Org. Chem., 1993, vol. 58, p. 1623.

    Article  CAS  Google Scholar 

  41. Cheney, B.V., J. Org. Chem., 1994, vol. 59, p. 773.

    Article  CAS  Google Scholar 

  42. Moody, C.J., Rees, C.W., and Young, R.G., Synlett., 1990, p. 413.

  43. Moody, C.J., Rees, C.W., and Young, R.G., J. Chem. Soc., Perkin Trans. I, 1991, p. 323.

  44. Rhonnstad, P. and Wensbo, D., Tetrahedron Lett., 2002, vol. 43, p. 3137.

    Article  CAS  Google Scholar 

  45. Lo, Y.S., Rossano, L.T., Meloni, D.J., Moore, J.R., Lee, Y.-C., and Arnett, J.F., J. Heterocyclic. Chem., 1995, vol. 32, p. 355.

    CAS  Google Scholar 

  46. Larsen, R.D., King, A.O., Chen, C.Y., Corley, E.G., Foster, B.S., Roberts, F.E., Yang, C., Lieberman, D.R., Reamer, R.A., Tschaen, D.M., Verhoeven, T.R., and Reider, P.J., J. Org. Chem., 1994, vol. 59, p. 6391.

    Article  CAS  Google Scholar 

  47. Shuman, R.F., King, A.O., and Anderson, R.K., US Patent 5039814, 1991; Chem. Abstr., 1991, vol. 115, 183324.

  48. Villa, M., Allegrini, P., Arrighi, K., and Paiocchi, M., Patent 9901459, 1999; WO. Chem. Abstr., 1999, vol. 130, 125212.

  49. Ellingboe, J.W., Nikaido, M., Bagli, J.F., Europe Patent 539086, 1993; Chem. Abstr., 1993, vol. 119, p. 95558.

  50. Huff, B.E., LeTourneau, M.E., Staszak, M.A., and Ward, J.A., Tetrahedron Lett., 1996, vol. 37, p. 3655.

    Article  CAS  Google Scholar 

  51. Dashkovskaya, E.V., Ignat'ev, H.V., Shivanyuk, A.F., and Lozinskii, M.O., Zh. Org. Khim.,, 1990, vol. 26, p. 205.

    CAS  Google Scholar 

  52. Blakemore, P.R., Cole, W.J., Kocienski, P.J., and Morley, A., Synlett., 1998, vol. 26.

  53. Kocienski, P.J., Bell, A., and Blakemore, P.R., Synlett., 2000, p. 365.

  54. Blakemore, P.R., J. Chem. Soc., Perkin Trans. I, 2002, p. 2563.

  55. Williams, D.R., Brooks, D.A., and Berliner, M.A., J. Am. Chem. Soc., 1999, vol. 121, p. 4924.

    CAS  Google Scholar 

  56. Blakemore, P.R., Kocienski, P.J., Morley, A., and Muir, K., J. Chem. Soc., Perkin Trans. I, 1999, p. 955.

  57. Smith, III, A.B. and Wan, Z., J. Org. Chem., 2002, vol. 65, p. 3738.

    Google Scholar 

  58. Smith, III, A.B., Adams, C.M., Kozmin, S.A., and Paone, D.V., J. Am. Chem. Soc., 2001, vol. 123, p. 5925.

    CAS  Google Scholar 

  59. Smith, III, A.B., Safonov, I.G., and Corbett, R.M., J. Am. Chem. Soc., 2001, vol. 123, p. 12426.

    CAS  Google Scholar 

  60. Kim, Y.K., Min, S.J., Son, S.H., Lim, S.M., and Jang, W.S., Angew. Chem., 2002, 1 vol. 14, p. 184.

    Google Scholar 

  61. Ahmed, A., Hoegenauer, E.K., Enev, V.S., Hanbauer, M., Kaehlig, H., Ohler, E., and Mulzer, J., J. Org. Chem., 2003, vol. 68, p. 3026.

    Article  CAS  Google Scholar 

  62. Takano, D., Nagamitsu, T., Ui, H., Shiomi, K., Yamaguchi, Y., Masuma, R., Kuwajima, I., and Ohmura, S., Org. Lett., 2001, vol. 3, p. 2289.

    Article  CAS  Google Scholar 

  63. Smith, III, A.B. and Brandt, B.M., Org. Lett., 2001, vol. 3, p. 1685.

    CAS  Google Scholar 

  64. Hayes, P.Y. and Kitching, W., J. Am. Chem. Soc., 2002, vol. 124, p. 9718.

    CAS  Google Scholar 

  65. Trost, B.M. and Crawley, M.L., J. Am. Chem. Soc., 2002, vol. 124, p. 9328.

    CAS  Google Scholar 

  66. Song, H.Y., Joo, J.M., Kang, J.W., Kim, D.-S., Jung, C.-K., Kwak, H.S., Park, J.H., Lee, E., Hong, C.Y., Jeong, S.W., Jeon, K. and Park, J.H., J. Org. Chem., 2003, vol. 68, p. 8080.

    Google Scholar 

  67. Kang, S.H., Kang, S.Y., Kim, C.M., Choi, H.-W., Jun, H.-S., Lee, B.M., Park, C.M. and Jeong, J.W., Angew. Chem., 2003, vol. 115, p. 4927.

    Article  Google Scholar 

  68. Trost, B.M., Chisholm, J.D., Wrobleski, S.T., and Jung, M., J. Am. Chem. Soc., 2002, vol. 124, p. 12420.

    CAS  Google Scholar 

  69. Smith, III, A.B., Safonov, I.G., and Corbett, R.M., J. Am. Chem. Soc., 2002, vol. 124, p. 11102.

    CAS  Google Scholar 

  70. Fettes, A. and Carreira, E.M., J. Org. Chem., 2003, vol. 68, p. 9274.

    Article  CAS  Google Scholar 

  71. Lautens, M., Colucci, J.T., Hiebert, S., Smith, N.D., and Bouchain, G., Org. Lett., 2002, vol. 4, p. 1879.

    CAS  Google Scholar 

  72. Hanessian, S., Yang, Y., Giroux, S., Mascitti, V., Ma, J., and Raeppel, F., J. Am. Chem. Soc., 2003, vol. 125, p. 13784.

    CAS  Google Scholar 

  73. Furstner, A., Albert, M., Mlynarski, J., Matheu, M., and DeClercq, E., J. Am. Chem. Soc., 2003, vol. 125, p. 13132.

    Article  Google Scholar 

  74. Ishigami, K. and Kitahara, T., Heterocycles, 2004, vol. 63, p. 785.

    CAS  Google Scholar 

  75. Wang, X., Bowman, E.J., Bowman, B.J., and Porco, J.A. Jr., Angew. Chem., 2004, vol. 116, p. 3685.

    Google Scholar 

  76. Kowashi, S., Ogamino, T., Kamei, J., Ishikawa, Y., and Nishiyama, S., Tetrahedron Lett., 2004, vol. 45, p. 4393.

    Article  CAS  Google Scholar 

  77. Jankowski, P., Plesniak, K., and Wicha, J., Org. Lett., 2003, vol. 5, p. 2789.

    Article  CAS  Google Scholar 

  78. Liepa, A.J., Jones, D.A., McCarthy, Th.D., and Nearn, R.H., Austr. J. Chem., 2003, vol. 56, p. 619.

    Google Scholar 

  79. Flippin, L.A., Tetrahedron Lett., 1991, vol. 32, p. 6857.

    Article  CAS  Google Scholar 

  80. Ek, F., Wistrand, L.-G., and Freid, T., Tetrahedron, 2003, vol. 59, p. 6759.

    Article  CAS  Google Scholar 

  81. Katrizky, A.R., Aslan, D., Shcherbakova, I.V., Chen, J., and Belyakov, S.A., J. Heterocyclic. Chem., 1996, vol. 33, p. 1107.

    Google Scholar 

  82. Shvekhgeimer, M.-G.A., Usp. Khim., 1996, vol. 65, p. 43.

    CAS  Google Scholar 

  83. Boev, V.I., Cnegur, L.V., Babin, V.H., and Hekrasov, Yu.C., Usp. Khim., 1997, vol. 66, p. 677.

    CAS  Google Scholar 

  84. Cachivko, A.V., Tverdokhlebov, V.P., and Tselinskii, I.V., Ros. Khim. Zh., 1997, vol. 41, no.2, p. 119.

    Google Scholar 

  85. Boev, V.I., Krasnikova, E.M., Moskalenko, A.I., Pil'ko, E.I., Cnegur, L.V., Babin, V.H., and Hekrasov, Yu.C., Zh. Obshch. Khim., 1997, vol. 67, p. 1386.

    Google Scholar 

  86. Krasnikova, E.M., Ilyushina, T.H., Moskalenko, A.I., and Boev, V.I., Zh. Org. Khim.,, 2002, vol. 38, p. 952.

    Google Scholar 

  87. Hirose, M., Kawai, R., and Hayakawa, Y., Synlett., 1997, p. 495.

  88. Krasnikova, E.M., Moskalenko, A.I., Kopaeva, H.A., and Boev, V.I., Zh. Obshch. Khim., 2003, vol. 73, p. 1554.

    Google Scholar 

  89. Boev, V.I., Betankourt, P.M., Popova, L.V., and Babin, V.H., Zh. Obshch. Khim., 1991, vol. 61, p. 1651.

    CAS  Google Scholar 

  90. Karpov, M.G., Zavgorodnii, V.C., Denisov, V.R., Ostrovskii, V.A., and Zubarev, V.Yu., Zh. Org. Khim.,, 2001, vol. 37, p. 1252.

    Google Scholar 

  91. Munoz-Hernandez, M.-A., Hill, M.S., and Atwood, D.A., Polyhedron, 1998, vol. 17, p. 2237.

    CAS  Google Scholar 

  92. Becker, T.M., Krause-Bauer, J.A., Homrighausen, C.L., and Orchin, M., Polyhedron, 1999, vol. 18, p. 2563.

    Article  CAS  Google Scholar 

  93. Pallazzi, A., Stangi, S., Bordoni, S., Monari, M., and Selva, S., Organometallics, 2002, vol. 21, p. 3774.

    Google Scholar 

  94. Schollhammer, P., Cabon, N., Kervella, A.-C., Petillon, F.Y., Rumin, R., Talarmin, J., and Muir, K.W., Inorg. Chim. Acta, 2003, vol. 350, p. 495.

    Article  CAS  Google Scholar 

  95. Chang, C.-W. and Lee, G.-H., Organometallics, 2003, vol. 22, p. 3107.

    CAS  Google Scholar 

  96. Huang, C.C., Lin, Y.C., Huang, S.L., Lui, Y.H., and Wang., Y,, Organometallics, 2003, vol. 22, p. 1512.

    CAS  Google Scholar 

  97. Pinillos, M.T., Elduque, A., Berkovich, E., and Oro, L.A., J. Organometal. Chem., 1996, vol. 509, p. 89.

    Article  CAS  Google Scholar 

  98. Kopaeva, H.A., Moskalenko, A.I., Krasnikova, E.M., and Boev, V.I., Zh. Org. Khim.,, 2002, vol. 38, p. 950.

    Google Scholar 

  99. Bhandari, S., Mahon, M.F., Molloy, K.C., Palmer, J.S., and Sayers, S.F., J. Chem. Soc., Dalton Trans., 2000, p. 1053.

  100. Semenov, B.B. and Smushkevich, Yu.I., Izv. Akad. Nauk, Ser. Khim., 2002, p. 334.

  101. Hill, M.S., Hitchcock, P.B., and Smith, N., Polyhedron, 2004, vol. 23, p. 801.

    Article  CAS  Google Scholar 

  102. Blunden, S.J., Mahon, M.F., Molloy, K.C., and Waterfield, P.C., J. Chem. Soc., Dalton Trans., 1994, p. 2135.

  103. Cheikh, Diop, A.K., and Molloy, K.C., Main Group Metal Chem., 2002, vol. 25, p. 267.

    Google Scholar 

  104. Bhandari, S., Frost, C.G., Hague, C.E., Mahon, M.F., and Molloy, K.C., J. Chem. Soc., Dalton Trans., 2000, p. 663.

  105. Goodger, A., Hill, M., Mahon, M.F., McGinley, J., and Molloy, K.C., J. Chem. Soc., Dalton Trans., 1996, p. 847.

  106. Hill, M., Mahon, M.F., McGinley, J., and Molloy, K.C., J. Chem. Soc., Dalton Trans., 1996, p. 835.

  107. Hill, M., Mahon, M.F., and Molloy, K.C., J. Chem. Soc., Dalton Trans., 1996, p. 1857.

  108. Bhandari, S.M., Mahon, F., and Molloy, K.C., J. Chem. Soc., Dalton Trans., 1999, p. 1951.

  109. Diop, C.A.K., Mahon, M.F., Molloy, K.C., Ooi, L., Raithby, P.R., Venter, M.M., and Teat, S., J. Cryst. Eng. Comm., 2002, vol. 4, p. 462.

    CAS  Google Scholar 

  110. Duncia, J.V., Pierce, M.E., and Santella, III, J.B., J. Org. Chem., 1991, vol. 56, p. 2395.

    Article  CAS  Google Scholar 

  111. Carini, D.J., Duncia, J.V., Aldrich, P.E., Chiu, A.T., Johnson, A.L., Pierce, M.E., Price, W.A., Santella, J.B. III, Wells, G.J., Wexler, R.R., Wong, P.C., Yoo, S.-E., and Timmermans, P.B.M.W.M., J. Med. Chem., 1991, vol. 34, p. 2525.

    Article  CAS  Google Scholar 

  112. O'Brien, P.M., Sliskovic, D.R., Picard, J.A., Lee, H.T., Purchase, C.F., Roth, B.D., White, A.D., Anderson, M., Bak, Mueller, S., Bocan, T., Bousley, R., Hamelehle, K.L., Homan, R., Lee, P., Krause, B.R., Reindel, J.F., Stanfield, R.L., and Turluck, D., J. Med. Chem., 1996, vol. 39, p. 2354.

    Article  Google Scholar 

  113. Ornstein, P.L., Arnold, M.B., Lunn, W.H.W., Heinz, L.J., Leander, J.D., Lodge, D., and Schoepp, D.D., Bioorg. Med. Chem. Lett., 1998, p. 389.

  114. McMurray, J.S., Khabashesku, O., Birtwistle, J.S., and Wang, W., Tetrahedron Lett., 2000, vol. 41, p. 6555.

    Article  CAS  Google Scholar 

  115. Butler, R.N., Comprehensive Heterocyclic Chemistry, Katritzky, A.R., Rees, C.W., Scriven, E.F.V., New York: Pergamon, 1996, vol. 4, p. 621.

    Google Scholar 

  116. Meier, H.R. and Heimgartner, H., Houben-Weyl Meth. Org. Chem., 1994, E8d, p. 664.

  117. Curran, D.P., Hadida, S., and Kim, S.Y., Tetrahedron, 1999, vol. 55, p. 8997.

    CAS  Google Scholar 

  118. Davydov, D.V., Beletskaya, I.P., Semenov, B.B., and Smushkevich, Y.I., Tetrahedron Lett., 2002, vol. 43, p. 6217.

    Article  CAS  Google Scholar 

  119. Bethel, P.A., Hill, M.S., Mahon, M.F., and Molloy, K.C., J. Chem. Soc., Perkin Trans. I, 1999, p. 3507.

Download references

Author information

Authors and Affiliations

  1. Research Institute of Physicochemical Problems, Belarussian State University, Minsk, 220050, Belarus

    S. V. Voitekhovich & P. N. Gaponik

  2. Saint-Petersburg State Technological Institute, St. Petersburg, 198013, Russia

    G. I. Koldobskii

Authors
  1. S. V. Voitekhovich
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. P. N. Gaponik
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. G. I. Koldobskii
    View author publications

    You can also search for this author in PubMed Google Scholar

Additional information

__________

Translated from Zhurnal Organicheskoi Khimii, Vol. 41, No. 11, 2005, pp. 1599–1616.

Original Russian Text Copyright © 2005 by Voitekhovich, Gaponik, Koldobskii.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Voitekhovich, S.V., Gaponik, P.N. & Koldobskii, G.I. Organometallic Tetrazole Derivatives: Preparation and Application to Organic Synthesis. Russ J Org Chem 41, 1565–1582 (2005). https://doi.org/10.1007/s11178-006-0001-4

Download citation

  • Received:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s11178-006-0001-4

Keywords

Search

Navigation