Skip to main content
Log in

1-Substituted 5-Alkyl(aryl)sulfanyltetrazoles and Their Derivatives

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

Abstract

The review analyzes published data on the synthesis, chemical properties, and application of 1-substituted 5-alkyl(aryl)sulfanyltetrazoles. Specific attention is given to reactions of metalated 1-alkyl(aryl)-5-alkylsulfonyltetrazoles with electrophilic reagents as a general and highly stereoselective method for the preparation of functionally substituted olefins.

This is a preview of subscription content, log in via an institution to check access.

Access this article

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. Koldobskii, G.I., Ostrovskii, V.A., and Poplavskii, V.S., Khim. Geterotsikl. Soedin., 1981, p. 1299.

  2. Koldobskii, G.I. and Ostrovskii, V.A., Usp. Khim., 1994, vol. 63, p. 847.

    Google Scholar 

  3. Wittenberg, S.J., Org. Prep. Proced. Int., 1994, vol. 26, p. 499.

    Google Scholar 

  4. Butler, R.N., Comprehensive Heterocyclic Chemistry II, Katritzky, A.R., Rees, C.W., and Scriven, E.F.V., Eds., Oxford: Pergamon, 1996, vol. 4, p. 621.

    Google Scholar 

  5. Voitekhovich, S.V., Gaponik, P.N., and Ivashkevich, O.A., Usp. Khim., 2002, vol. 71, p. 819.

    Google Scholar 

  6. Kizhnyaev, V.N. and Vereshchagin, L.I., Usp. Khim., 2003, vol. 72, p. 159.

    Google Scholar 

  7. Koldobskii, G.I. and Kharbash, R.V., Russ. J. Org.Chem., 2003, vol. 39, p. 453.

    Google Scholar 

  8. Blakemore, P.R., Cole, W.J., Kocienski, P.J., and Morley, A., Synlett, 1998, p. 26.

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

  10. Blakemore, P.R., J. Chem. Sos. Perkin Trans. 1, 2002, p. 2563.

  11. Elguero, J., Marzin, C., Katritzky, A.R., and Linda, P., The Tautomerism of Heterocycles, New York: Academic, 1976.

    Google Scholar 

  12. Bojarska-Olejnik, E., Stefaniak, L., Witanowski, M., and Webb, G.A., Bull. Chem. Soc. Jpn., 1986, vol. 59, p. 3263.

    Google Scholar 

  13. Poplavskaya, Yu.V., Trifonov, R.E., Shcherbinin, M.B., and Koldobskii, G.I., Russ. J. Org. Chem., 2000, vol. 36, p. 1788.

    Google Scholar 

  14. Hunig, S. and Oette, K.H., Justus Liebigs Ann. Chem., 1961, vol. 641, p. 94.

    Google Scholar 

  15. Nirenburg, V.L., Postovskii, I.Ya., and Chertkova, E.I., Izv. Vyssh. Uchebn. Zaved., Ser. Khim. Khim. Tekhnol. 1965, vol. 8, p. 258.

    Google Scholar 

  16. Neidlein, R. and Tauber, J., Chem. Ber., 1967, vol. 100, p. 736.

    Google Scholar 

  17. Alper, H. and Stout, R.W., J. Heterocycl. Chem., 1973, vol. 10, p. 569.

    Google Scholar 

  18. Bartels-Keith, J.R., Mahoney, J.B., and Puttick, A.J., J. Org. Chem., 1985, vol. 50, p. 980.

    Google Scholar 

  19. Quast, H. and Nahr, U., Chem. Ber., 1985, vol. 118, p. 526.

    Google Scholar 

  20. Uchida, M., Komatsu, M., Morita, S., Kanbe, T., Yamasaki, K., and Nakagawa, K., Chem. Pharm. Bull., 1989, vol. 37, p. 958.

    Google Scholar 

  21. Waisser, K., Vanžura, J., Hrabalek, A., Vinšova, J., Grešak, Š., Hruška, J., and Odlerova, Ž., Collect. Czech.Chem. Commun., 1991, vol. 56, p. 2389.

    Google Scholar 

  22. Földényi, R., Monatsh. Chem., 1995, vol. 126, p. 1035.

    Google Scholar 

  23. Waisser, K., Kuneš, J., Hrabalek, A., Macháček, M., and Odlerova, Ž., Collect. Czech. Chem. Commun., 1996, vol. 61, p. 791.

    Google Scholar 

  24. Blakemore, P.R., Kocieński, P.J., Morley, A., and Muir, K., J. Chem. Soc. Perkin Trans. 1, 1999, p. 955.

  25. Compostella, F., Franchini, L., Panza, L., Prosperi, D., and Ronchetti, F., Tetrahedron, 2002, vol. 58, p. 4425.

    Google Scholar 

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

    Google Scholar 

  27. Mitsunobu, O., Synthesis, 1981, p. 1.

  28. Smith, A.B., III and Wan, Z., Org. Lett., 1999, vol. 1, p. 1491.

    Google Scholar 

  29. Metternich, R., Denni, D., Thai, B., and Sedrani, R., J. Org. Chem., 1999, vol. 64, p. 9632.

    Google Scholar 

  30. Smith, A.B., III and Wan, Z., J. Org. Chem., 2000, vol. 65, p. 3738.

    Google Scholar 

  31. Williams, D.R., Clark, M.P., Emde, U., and Berliner, M., Org. Lett., 2000, vol. 2, p. 3023.

    Google Scholar 

  32. Seki, M. and Mori, K., Eur. J. Org. Chem., 2001, p. 503.

  33. . Kang, S.H., Jeong, J.W., Hwang, Y.S., and Lee, S.B., Angew. Chem., Int. Ed., 2002, vol. 41, p. 1392.

    Google Scholar 

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

    Google Scholar 

  35. Quast, H. and Bieber, L., Chem. Ber., 1981, vol. 114, p. 3253.

    Google Scholar 

  36. Narisada, M., Terui, Y., Yamakawa, M., Watanabe, F., Ohtani, M., and Miyazaki, H., J. Org. Chem., 1985, vol. 50, p. 2794.

    Google Scholar 

  37. L'abbe, G., Vermeulen, G., Flémal, J., and Toppet, S., J. Org. Chem., 1976, vol. 41, p. 1875.

    Google Scholar 

  38. Lippmann, E. and Reifegerste, D., Z. Chem., 1975, vol. 15, p. 146.

    Google Scholar 

  39. Cheng, S. and Comer, D.D., Tetrahedron Lett., 2002, vol. 43, p. 1179.

    Google Scholar 

  40. 40. Nirinburg, V.L. and Postovskii, I.Ya., Zh. Obshch.Khim., 1964, vol. 34, p. 3200.

    Google Scholar 

  41. Krutak, J.J., Burpitt, R.D., Moore, W.H., and Hyatt, J.A., J. Org. Chem., 1979, vol. 44, p. 3847.

    Google Scholar 

  42. Waisser, K., Kuneš, J., Hrabalek, A., and Macháček, M., Proc. XIth Symp. on Chemistry of Heterocyclic Compounds, Prague, 1993, p. 68.

  43. Kuneš, J., Hrabalek, A., Macháček, M., Waisser, K., and Olderova, Ž., Proc. XIIth Symp. on Chemistry of Heterocyclic Compounds, Brno, 1996, p. 90.

  44. Gol'tsberg, M.A. and Koldobskii, G.I., Russ. J. Org.Chem., 1996, vol. 32, p. 1194.

    Google Scholar 

  45. Gol'tsberg, M.A., Hrabalek, A., Farsa, O., Krebs, A., Dolezhal, P., and Koldobskii, G.I., Russ. J. Org. Chem., 1996, vol. 32, p. 1367.

    Google Scholar 

  46. Koreneva, A.P., Farsa, O., Hrabalek, A., and Koldobskii, G.I., Russ. J. Org. Chem., 1999, vol. 35, p. 1820.

    Google Scholar 

  47. Dehmlow, E.V. and Dehmlow, S.S., Phase-Transfer Catalysis, New York: VCH, 1993.

    Google Scholar 

  48. Dehmlov, E., Izv. Ross. Akad. Nauk, Ser. Khim., 1995, p. 2094.

  49. Koldobskii, G.I., Izv. Ross. Akad. Nauk, Ser. Khim., 1995, p. 2115.

  50. Dehmlow, E.V., Phase-Transfer Catalysis. Mechanisms and Synthesis, Halpern, M.E., Ed., Washington: Am.Chem. Soc., 1996, p. 108.

    Google Scholar 

  51. Finnegan, W.G., Henry, R.A., and Lofquist, R., J. Am.Chem. Soc., 1958, vol. 80, p. 3908.

    Google Scholar 

  52. Lieber, E. and Enkoji, T., J. Org. Chem., 1961, vol. 26, p. 4472.

    Google Scholar 

  53. Le Blanc, B.W. and Jursic, B.S., Synth. Commun., 1998, vol. 28, p. 3591.

    Google Scholar 

  54. Demko, Z.P. and Sharpless, K.B., J. Org. Chem., 2001, vol. 66, p. 7945.

    Google Scholar 

  55. Demko, Z.P. and Sharpless, K.B., Org. Lett., 2001, vol. 3, p. 4091.

    Google Scholar 

  56. Raap, R. and Howard, J., Can. J. Chem., 1969, vol. 47, p. 813.

    Google Scholar 

  57. Ostrovskii, V.A. and Koren, A.O., Heterocycles, 2000, vol. 53, p. 1421.

    Google Scholar 

  58. 58. Alam, L.V. and Koldobskii, G.I., Russ. J. Org. Chem., 1997, vol. 33, p. 1149.

    Google Scholar 

  59. Smirnova, G.G., Kovaleva, O.P., Artamonova, T.V., Koreneva, A.P., and Koldobskii, G.I., Russ. J. Org.Chem., 2003, vol. 39, p. 1679.

    Google Scholar 

  60. Osipova, T.F., Ostrovskii, V.A., Koldobskii, G.I., and Erusalimskii, G.B., Zh. Org. Khim., 1984, vol. 20, p. 398.

    Google Scholar 

  61. Lippmann, E., Könnecke, A., and Beyer, G., Z. Chem., 1975, vol. 15, p. 54.

    Google Scholar 

  62. Henry, R.A., J. Heterocycl. Chem., 1976, vol. 13, p. 391.

    Google Scholar 

  63. O'Brien, D.F., J. Org. Chem., 1968, vol. 33, p. 262.

    Google Scholar 

  64. Schmidt, U. and Dietsche, M., Angew. Chem., Int. Ed.Engl., 1982, vol. 21, p. 143.

    Google Scholar 

  65. Galli, R., Palla, O., and Gozzo, F., J. Chem. Soc., Perkin Trans. 1, 1982, p. 2813.

    Google Scholar 

  66. Butler, R.N., Ni Bhradaigh, E.P., and Fitzgerald, K.J., J. Chem. Res., Synop., 1993, p. 306.

  67. Petko, K.I. and Yagupol'skii, L.P., Russ. J. Org. Chem., 2004, vol. 40, p. 601.

    Google Scholar 

  68. Lehn, J.-M., Supramolecular Chemistry: Concepts and Perspectives, Weinheim: VCH, 1995.

    Google Scholar 

  69. Schneider, H.-J. and Yatsimirsky, A.K., Principles and Methods in Supramolecular Chemistry, Chichester: Wiley, 1999.

    Google Scholar 

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

  71. Bhandari, S., Mahon, M.F., McGinley, J.G., Molloy, K.C., and Roper, C.E.E., J. Chem. Soc., Dalton Trans., 1998, p. 3425.

  72. Barret, M., Bhandari, S., Mahon, M.F., and Molloy, K.C., J. Organomet. Chem., 1999, vol. 587, p. 101.

    Google Scholar 

  73. Scott, F.L., Britten, VF.C., and Reilly, J., J. Org. Chem., 1956, vol. 21, p. 1191.

    Google Scholar 

  74. Koreneva, A.P. and Koldobskii, G.I., Russ. J. Org.Chem., 1999, vol. 35, p. 1511.

    Google Scholar 

  75. Baudin, J.B., Hareau, G., Julia, S.A., and Ruel, O., Tetrahedron Lett., 1991, vol. 32, p. 1175.

    Google Scholar 

  76. Taylor, L.D., Grasshoff, J.M., and Pluhar, M., J. Org.Chem., 1978, vol. 43, p. 1197.

    Google Scholar 

  77. Takeda, K., Tsuboyama, K., Torii, K., Murata, M., and Ogura, H., Tetrahedron Lett., 1988, vol. 29, p. 4105.

    Google Scholar 

  78. Takeda, K., Torii, K., and Ogura, H., Tetrahedron Lett., 1990, vol. 31, p. 265.

    Google Scholar 

  79. 79. Kharbash, R.V., Gol'tsberg, M.A., Artamonova, T.V., Nordlander, E., and Koldobskii, G.I., Russ. J. Org.Chem., 2002, vol. 38, p. 1356.

    Google Scholar 

  80. Beletskaya, I.P. and Chuchuryukin, A.V., Usp. Khim., 2000, vol. 69, p. 699.

    Google Scholar 

  81. Demko, Z.P. and Sharpless, K.B., Angew. Chem., Int.Ed., 2002, vol. 41, p. 2110.

    Google Scholar 

  82. Tόth, J. and Simon, Z., Monatsh. Chem., 1994, vol. 125, p. 977.

    Google Scholar 

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

    Google Scholar 

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

    Google Scholar 

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

    Google Scholar 

  86. Lee, E., Song, Y., Kang, J.W., Kim, D.-S., Jung, C.-K., and Joo, J.M., J. Am. Chem. Soc., 2002, vol. 124, p. 384.

    Google Scholar 

  87. Ueda, I., Ishii, K., Sinozaki, K., Seiki, M., and Hatanaka, M., Chem. Pharm. Bull., 1991, vol. 39, p. 1430.

    Google Scholar 

  88. Morita, H., Takeda, M., Yoshimura, T., Fujii, T., Ono, S., and Shimasaki, C., J. Org. Chem., 1999, vol. 64, p. 6730.

    Google Scholar 

  89. Lee, E., Choi, S.J., Kim, H., Han, H.O., Kim, Y.K., Min, S.J., Son, S.H., Lim, S.M., and Jang, W.S., Angew. Chem., Int. Ed., 2002, vol. 41, p. 176.

    Google Scholar 

  90. Alper, H. and Stout, R.W., J. Heterocycl. Chem., 1973, vol. 10, p. 5.

    Google Scholar 

  91. Takeda, M., Yoshimura, T., Fujii, T., Ono, S., Shimasaki, C., and Morita, H., Tetrahedron Lett., 1999, vol. 40, p. 2327.

    Google Scholar 

  92. Altland, H.W., J. Org. Chem., 1976, vol. 41, p. 21.

    Google Scholar 

  93. Ishii, K., Hatanaka, M., and Ueda, I., Chem. Pharm.Bull., 1991, vol. 39, p. 3331.

    Google Scholar 

  94. Butler, R.N., Ni Bhradaigh, E.P., and Firzgerald, K.J., J. Chem. Res., Synop., 1994, p. 196.

  95. Saleh, G.A., Askal, H.F., Darwish, I.A., and El-Shorbagi, A.-N.A., Anal. Sci., 2003, vol. 19, p. 281.

    Google Scholar 

  96. Powers, R.A. and Shoichet, B.K., J. Med. Chem., 2002, vol. 45, p. 3222.

    Google Scholar 

  97. Lee, P.-Y., Chang, W.-N., Lu, C.-H., Lin, M.-W., Cheng, B.-C., Chien, C.-C., Chang, C.-J., and Chang, H.-W., J. Antimicrob. Chemother., 2003, vol. 51, p. 957.

    Google Scholar 

  98. Hilali, A., Jiménez, J.C., Callejon, M., Bello, M.A., and Guiraúm, A., Talanta, 2003, vol. 59, p. 137.

    Google Scholar 

  99. Yakovlev, V.P., Antibiot. Khimioter., 1993, vol. 38, p. 50.

    Google Scholar 

  100. Yakovlev, V.P. and Kaplar-Vuchevats, M., Antibiot.Khimioter., 1994, vol. 39, p. 56. 1-

    Google Scholar 

  101. Navashin, S.M., Antibiot. Khimioter., 1995, vol. 40, p. 11.

    Google Scholar 

  102. Brussel, W.V., Specialty Chem., 1996, vol. 16, p. 142.

    Google Scholar 

  103. Vanžura, J., Hrabalek, A., Odlerova, Ž., Waisser, K., and Čeladnik, M., Českoslov. Farm., 1985, vol. 34, p. 271.

    Google Scholar 

  104. O'Neill, M.J., Bond, A., Ornstein, P.L., Ward, M.A., Hicks, C.A., Hoo, K., Bleakman, D., and Lodge, D., Neuropharmacology, 1998, vol. 37, p. 1211.

    Google Scholar 

  105. Kejha, J., Slukova, D., Brůnova, B., Maturova, E., and Grimova, J., Českoslov. Farm., 1990, vol. 39, p. 294.

    Google Scholar 

  106. Brand, S., de Candole, B.C., and Brown, J.A., Org. Lett., 2003, vol. 5, p. 2343.

    Google Scholar 

  107. Krasnyi-Admoni, L.V., Maloserebryanye fotograficheskie materialy i protsessy ikh obrabotki (Low-Silver Photographic Materials and Procedures for Their Treatment), Leningrad: Khimiya. 1986.

    Google Scholar 

  108. Sowinski, A.F., Eur. Patent no. 1 324 127, 2003; Chem.Abstr., 2003, vol. 139, no. 76301.

  109. Slusarek, W.K., Yang, X., Levy, D.H., and Nothhard, L.B., US Patent no. 6 558 890, 2003; Chem.Abstr., 2003, vol. 138, no. 360 351.

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

    Google Scholar 

  111. Mulzer, J. and Öhler, E., Angew. Chem., Int. Ed., 2001, vol. 40, p. 3842.

    Google Scholar 

  112. Liu, P. and Jacobsen, E.N., J. Am. Chem. Soc., 2001, vol. 123, p. 10772.

    Google Scholar 

  113. Hilpert, H. and Wirz, B., Tetrahedron, 2001, vol. 57, p. 681.

    Google Scholar 

  114. Crich, D. and Dudkin, V., J. Am. Chem. Soc., 2002, vol. 124, p. 2263.

    Google Scholar 

  115. Fürstner, A., Mlynarski, J., and Albert, M., J. Am.Chem. Soc., 2002, vol. 124, p. 10274.

    Google Scholar 

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

    Google Scholar 

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

  118. 118. Sedrani, R., Kallen, J., Cabrejas, L.M.M., Papageorgiou, C.D., Senia, F., Rohrbach, S., Wagner, D., Thai, B., Eme, A.-M.J., France, J., Oberer, L., Rihs, G., Zenke, G., and Wagner, J., J. Am. Chem.Soc., 2003, vol. 125, p. 3849.

    Google Scholar 

  119. Meyers, C. and Carreira, E.M., Angew. Chem., Int. Ed., 2003, vol. 42, p. 694.

    Google Scholar 

  120. Williams, D.R., Kiryanov, A.A., Emde, U., Clark, M.P., Berliner, M.A., and Reeves, J.T., Angew.Chem., Int. Ed., 2003, vol. 42, p. 1258.

    Google Scholar 

  121. Jankowski, P., Pleśniak, K., and Wicha, J., Org. Lett., 2003, vol. 5, p. 2789.

    Google Scholar 

Download references

Author information

Authors and Affiliations

Authors

Rights and permissions

Reprints and permissions

About this article

Cite this article

Koldobskii, G.I., Hrabalek, A. & Esikov, K.A. 1-Substituted 5-Alkyl(aryl)sulfanyltetrazoles and Their Derivatives. Russian Journal of Organic Chemistry 40, 447–461 (2004). https://doi.org/10.1023/B:RUJO.0000036061.40446.49

Download citation

  • Issue Date:

  • DOI: https://doi.org/10.1023/B:RUJO.0000036061.40446.49

Keywords

Navigation