Skip to main content
SpringerLink
Log in

1,2,4,5-Tetrazines and Azolo[1,2,4,5]tetrazines: Synthesis and Reactions with Nucleophiles

  • Published:
Chemistry of Heterocyclic Compounds Aims and scope

The literature data are summarized for synthetic methods and nucleophilic transformations of 1,2,4,5-tetrazines and azolo[1,2,4,5]tetrazines published predominantly from 1995 until 2012.

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. P. F. Wiley, in: A. Weissberger and E. C. Taylor (editors), The Chemistry of Heterocyclic Compounds, Vol. 33, John Wiley & Sons, New York (1978).

  2. H. Neunhöffer, in: A. J. Boulton and A. McKillop (editors), Comprehensive Heterocyclic Chemistry, Vol. 3, Pergamon, Oxford (1984), p. 531.

    Chapter  Google Scholar 

  3. J. Sauer, in: A. R. Katritzky, C. W. Rees, and E. F. V. Scriven (editors), Comprehensive Heterocyclic Chemistry II, Vol. 6, Pergamon, Oxford (1996), p. 901.

    Chapter  Google Scholar 

  4. H. Neunhöffer, in: E. Schaumann (editor), Houben-Weyl Methods of Organic Chemistry, Vol. E9c, Georg Thieme Verlag, Stuttgart (1998), p. 870.

    Google Scholar 

  5. M. Bohler, in: S. M. Weinrib (editor), Science of Synthesis, Houben-Weyl Methods of Molecular Transformations, Vol. 117, Georg Thieme Verlag, Stuttgart (2006), p. 585.

    Google Scholar 

  6. B. Stanovik, U. Grošelj, and J. Svete, in: A. R. Katritzky, C. A. Ramsden, E. F. V. Scriven, and R. J. K. Taylor (editors), Comprehensive Heterocyclic Chemistry III, Vol. 9, Elsevier (2008), p. 641.

  7. N. Saracoglu, Tetrahedron, 63, 4199 (2007).

    Article  CAS  Google Scholar 

  8. E. G. Kovalev, I. Ya. Postovskii, G. L. Rusinov, and I. L. Shegal, Khim. Geterotsikl. Soedin., 1462 (1981). [Chem. Heterocycl. Compd., 17, 1063 (1981)].

    Google Scholar 

  9. J. Sauer, Khim. Geterotsikl. Soedin., 1307 (1995). [Chem. Heterocycl. Compd., 31, 1140 (1995)].

  10. G. Clavier and P. Audebert, Chem. Rev., 110, 3299 (2010).

    Article  CAS  Google Scholar 

  11. J. Soloducho, J. Doskocz, J. Cabaj, and S. Roszak, Tetrahedron, 59, 4761 (2003).

    Article  CAS  Google Scholar 

  12. G.-W. Rao and W.-X. Hu, Bioorg. Med. Chem. Lett., 16, 3702 (2006).

    Article  CAS  Google Scholar 

  13. P. Audebert, S. Sadki, F. Miomandre, G. Clavier, M. C. Vernieres, M. Saoud, and P. Hapiot, New J. Chem., 28, 387 (2004).

    Article  CAS  Google Scholar 

  14. I. Janowska, F. Miomandre, G. Clavier, P. Audebert, J. Zakrzewski, K. H. Thi, and I. Ledoux-Rak, J. Phys. Chem. A, 110, 12971 (2006).

    Article  CAS  Google Scholar 

  15. J. Sauer, G. R. Pabst, U. Holland, H.-S. Kim, and S. Loebbecke, Eur. J. Org. Chem., 697 (2001).

  16. R. A. Bowie, M. D. Gardner, D. G. Neilson, K. M. Watson, S. Mahmood, and V. Ridd, J. Chem. Soc., Perkin Trans. 1, 2395 (1972).

  17. J. Sauer, D. K. Heldmann, J. Hetzenegger, J. Krauthan, H. Sichert, and J. Schuster, Eur. J. Org. Chem., 2885 (1998).

  18. E. Sagot, A. Le Roux, C. Soulivet, E. Pasquinet, D. Poullain, E. Girard, and P. Palmas, Tetrahedron, 63, 11189 (2007).

    Article  CAS  Google Scholar 

  19. J. Yang, M. R. Karver, W. Li, S. Sahu, and N. K. Devaraj, Angew. Chem., Int. Ed., 51, 5222 (2012).

    Article  CAS  Google Scholar 

  20. K.-P. Hartmann and M. Heuschmann, Tetrahedron, 56, 4213 (2000).

    Article  CAS  Google Scholar 

  21. J. Sandstrom, Acta Chem. Scand., 15, 1575 (1961).

    Article  CAS  Google Scholar 

  22. J. L. Johnson, B. Whitney, and L. M. Werbel, J. Heterocycl. Chem., 17, 501 (1980).

    Article  CAS  Google Scholar 

  23. S. C. Fields, M. H. Parker, and W. R. Erickson, J. Org. Chem., 59, 8284 (1994).

    Article  CAS  Google Scholar 

  24. V. A. Ershov and I. Ya. Postovskii, Khim. Geterotsikl. Soedin., 571 (1971). [Chem. Heterocycl. Compd., 7, 537 (1971)].

    Google Scholar 

  25. U. Schirmer, B. Wuerzer, N. Meyer, F. A. Neugebauer, and H. Fischer, DE Pat. Appl. 3508214(A1).

  26. D. E. Chavez and M. A. Hiskey, J. Energ. Mater., 17, 357 (1999).

    Article  CAS  Google Scholar 

  27. M. D. Helm, A. Plant, and J. P. A. Harrity, Org. Biomol. Chem., 4, 4278 (2006).

    Article  CAS  Google Scholar 

  28. M. D. Coburn, G. A. Buntain, B. W. Harris, M. A. Hiskey, K.-Y. Lee, and D. G. Ott, J. Heterocycl. Chem., 28, 2049 (1991).

    Article  CAS  Google Scholar 

  29. S. M. Sakaya, K. K. Groskopf, and D. L. Boger, Tetrahedron Lett., 38, 3805 (1997).

    Article  Google Scholar 

  30. D. L. Boger, R. P. Schaum, and R. M. Garbaccio, J. Org. Chem., 63, 6329 (1998).

    Article  CAS  Google Scholar 

  31. A. Hamasaki, T. Ducray, and D. L. Boger, J. Org. Chem., 71, 185 (2006).

    Article  CAS  Google Scholar 

  32. J. S. Panek and B. Zhu, Tetrahedron Lett., 37, 8151 (1996).

    Article  CAS  Google Scholar 

  33. N. Leconte, A. Keromnes-Wuillaume, F. Suzenet, and G. Guillaumet, Synlett, 204 (2007).

  34. S. G. Tolshchina, R. I. Ishmetova, N. K. Ignatenko, A. V. Korotina, I. N. Ganebnykh, V. A. Ol'shevskaya, V. N. Kalinin, and G. L. Rusinov, Izv. Akad. Nauk, Ser. Khim., 961 (2011) [Russ. Chem. Bull., 60, 985 (2011)].

    Google Scholar 

  35. D. L. Boger and S. E. Wolkenberg, J. Org. Chem., 65, 9120 (2000).

    Article  CAS  Google Scholar 

  36. L. Pellegatti, E. Vedrenne, J.-M. Leger, C. Jarry, and S. Routier, Tetrahedron, 66, 4383 (2010).

    Article  CAS  Google Scholar 

  37. H. Yamanaka and S. Ohba, Heterocycles, 31, 895 (1990).

    Article  CAS  Google Scholar 

  38. G. Seitz and J. Richter, Chem. Ber., 122, 2177 (1989).

    Article  CAS  Google Scholar 

  39. K.-D. Topp and M. Grote, React. Funct. Polym., 31, 117 (1996).

    Article  CAS  Google Scholar 

  40. I. Ya. Postovskii, V. A. Ershov, E. O. Sidorov, and N. V. Serebryakova, Khim. Geterotsikl. Soedin., 1564 (1977). [Chem. Heterocycl. Compd., 13, 1253 (1977)].

  41. Z. Novak, V. Bostai, M. Csekei, K. Loerincz, and A. Kotschy, Heterocycles, 60, 2653 (2003).

    Article  CAS  Google Scholar 

  42. Y.-H. Gong, F. Miomandre, R. Meallet-Renault, S. Badre, I. Galmiche, J. Tang, P. Audebert, and G. Clavier, Eur. J. Org. Chem., 6121 (2009).

  43. Z. Qing, P. Audebert, G. Clavier, F. Miomandre, J. Tang, T. T. Vu, and R. Meallet-Renault, J. Electroanal. Chem., 632, 39 (2009).

    Article  CAS  Google Scholar 

  44. Y.-H. Gong, P. Audebert, J. Tang, F. Miomandre, G. Clavier, S. Badre, R. Meallet-Renault, and J. Marrot, J. Electroanal. Chem., 592, 147 (2006).

    Article  CAS  Google Scholar 

  45. Y.-H. Gong, P. Audebert, G. Clavier, F. Miomandre, J. Tang. S. Badre, R. Meallet-Renault, and E. Naidus, New J. Chem., 32, 1235 (2008).

    Google Scholar 

  46. C. Dumas-Verdes, F. Miomandre, E. Lepicier, O. Galangau, T. T. Vu, G. Clavier, R. Meallet-Renault, and P. Audebert, Eur. J. Org. Chem., 2525 (2010).

  47. P. Audebert, F. Miomandre, G. Clavier, M.-C. Vernieres, S. Badre, and R. Meallet-Renault, Chem. Eur. J., 11, 5667 (2005).

    Article  CAS  Google Scholar 

  48. Y. Kim. J. Do, E. Kim, G. Clavier, L. Galomiche, and P. Audebert J. Electroanal. Chem., 632, 201 (2009).

    Google Scholar 

  49. M. J. Tucker, J. R. Courter, J. Chen, O. Atasoylu, A. B. Smith, and R. M. Hochstrasser, Angew. Chem., Int. Ed., 49, 3612 (2010).

    Article  CAS  Google Scholar 

  50. S. C. Benson, L. Lee, L. Yang, and J. K. Snyder, Tetrahedron, 56, 1165 (2000).

    Article  CAS  Google Scholar 

  51. Z. Novak and A. Kotschy, Org. Lett., 5, 3495 (2003).

    Article  CAS  Google Scholar 

  52. N. I. Latosh, G. L. Rusinov, I. N. Ganebnykh, and O. N. Chupakhin, Zh. Org. Khim., 35, 1392 (1999). [Russ. J. Org. Chem., 35, 1363 (1999)].

    Google Scholar 

  53. G. L. Rusinov, N. I. Latosh, I. N. Ganebnykh, R. I. Ishmetova, N. K. Ignatenko, and O. N. Chupakhin, Zh. Org. Khim., 42, 772 (2006). [Russ. J. Org. Chem., 42, 757 (2006)].

    Google Scholar 

  54. D. Nhu, S. Duffy, V. M. Avery, A. Hughes, and J. B. Baell, Bioorg. Med. Chem. Lett., 20, 4496 (2010).

    Article  CAS  Google Scholar 

  55. C. Glidewell, P. Lightfoot, B. J. L. Royles, and D. M. Smith, J. Chem. Soc., Perkin Trans. 2, 1167 (1997).

  56. M. D. Helm, J. E. Moore, A. Plant, and J. P. A. Harrity, Angew. Chem., Int. Ed., 44, 3889 (2005).

    Article  CAS  Google Scholar 

  57. G. L. Rusinov, N. I. Latosh, R. I. Ishmetova, M. A. Kravchenko, I. N. Ganebnykh, V. A. Sokolov, and O. N. Chupakhin, Pharm. Chem. J., 39, 8 (2005).

    Article  CAS  Google Scholar 

  58. A. B. Sheremetev, N. V. Palysaeva, K. Yu. Suponitskii, and M. I. Struchkova, Izv. Akad. Nauk, Ser. Khim., 119 (2012).

  59. S. G. Tolshchina, A. G. Vyakhireva, I. K. Ignatenko, R. I. Ishmetova, I. N. Ganebnykh, P. A. Slepukhin, and G. L. Rusinov, Izv. Akad. Nauk, Ser. Khim., 2045 (2009). [Russ. Chem. Bull., 58, 1281 (2009)].

    Google Scholar 

  60. S. G. Tolshchina, N. K. Ignatenko, P. A. Slepukhin, R. I. Ishmetova, and G. L. Rusinov, Khim. Geterotsikl. Soedin., 860 (2010). [Chem. Heterocycl. Compd., 46, 691 (2010)].

    Google Scholar 

  61. A. Cutivet, E. Leroy, E. Pasquinet, and D. Poullain, Tetrahedron Lett., 49, 2748 (2008).

    Article  CAS  Google Scholar 

  62. D. E. Chavez, M. A. Hiskey, and R. D. Gilardi, Org. Lett., 6, 2889 (2004).

    Article  CAS  Google Scholar 

  63. D. E. Chavez, M. A. Hiskey, and D. L. Naud, Propellants, Explos., Pyrotech., 29, 209 (2004).

  64. D. E. Chavez and D. A. Parrish, J. Heterocycl. Chem., 46, 88 (2009).

    Article  CAS  Google Scholar 

  65. A. B. Sheremetev, N. V. Palysaeva, and M. I. Struchkova, Mendeleev Commun., 20, 350 (2010).

    Article  CAS  Google Scholar 

  66. D. E. Chavez, M. A. Hiskey, and R. D. Gilardi, Angew. Chem., Int. Ed., 39, 1791 (2000).

    Article  CAS  Google Scholar 

  67. M. B. Talawar, R. Sivabalan, N. Senthilkumar, G. Prabhu, and S. N. Asthana, J. Hazard. Mater., A113, 11 (2004).

    Article  Google Scholar 

  68. W.-L. Pan, K.-L. Huang, W. Tang, Y.-Q. Xu, and C.-W. Hu, Chin. J. Chem., 25, 1451 (2007).

    Article  CAS  Google Scholar 

  69. M. H. V. Nuynh, M. A. Hiskey, J. G. Archuleta, E. I. Roemer, and R. Gilardi, Angew. Chem., Int. Ed., 43, 5658 (2004).

    Article  Google Scholar 

  70. M. H. V. Huynh, M. A. Hiskey, D. E. Chavez, D. L. Naud, and R. D. Gilardi, J. Am. Chem. Soc., 127, 12537 (2005).

    Article  CAS  Google Scholar 

  71. R. I. Ishmetova, N. I. Latosh, I. N. Ganebnykh, N. K. Ignatenko, S. G. Tolshchina, and G. L. Rusinov, Zh. Org. Khim., 45, 1113 (2009). [Russ. J. Org. Chem., 45, 1102 (2009)].

    Google Scholar 

  72. S. G. Tolshchina, R. I. Ishmetova, N. K. Ignatenko, A. V. Korotina, P. A. Slepukhin, G. L. Rusinov, and V. N. Charushin, "Synthesis and transformations of cyanomethyl-1,2,4,5-tetrazines, Khim. Geterotsikl. Soedin., in press (2013).

  73. N. Gombosuren, Z. Novak, A. Kotschy, E. Mincsovics, and G. Dibo, J. Biochem. Biophys. Methods, 69, 239 (2007).

    Article  CAS  Google Scholar 

  74. G. L. Rusinov, R. I. Ishmetova, I. N. Ganebnykh, and O. N. Chupakhin, Heterocycl. Commun., 12, 99 (2006).

    Article  CAS  Google Scholar 

  75. R. I. Ishmetova, N. K. Ignatenko, I. N. Ganebnykh, S. G. Tolshchina, P. A. Slepukhin, and G. L. Rusinov, Heterocycles, 83, 1363 (2011).

    Article  CAS  Google Scholar 

  76. B. Bostai, Z. Novak, A. C. Benyei, and A. Kotschy, Org. Lett., 9, 3437 (2007).

    Article  CAS  Google Scholar 

  77. A. Counotte-Potman and H. C. van der Plas, J. Heterocycl. Chem., 18, 123 (1981).

    Article  CAS  Google Scholar 

  78. A. Counotte-Potman, H. C. van der Plas, and B. van Veldhuizen, J. Org. Chem., 46, 2138 (1981).

    Article  CAS  Google Scholar 

  79. J. Farago, Z. Novak, G. Schlosser, A. Csampai, and A. Kotschy, Tetrahedron, 60, 1991 (2004).

    Article  CAS  Google Scholar 

  80. M. C. Wilkes, J. Heterocycl. Chem., 28, 1163 (1991).

    Article  CAS  Google Scholar 

  81. K. Lorincz, A. Kotschy, J. Tammiku-Taul, L. Sikk, and P. Burk, J. Org. Chem., 75, 6196 (2010).

    Article  CAS  Google Scholar 

  82. D. Hunter and D. G. Neilson, J. Chem. Soc., Perkin Trans. 1, 1081 (1985).

  83. M. J. Haddadin and E. H. Ghazvini Zadeh, Tetrahedron Lett., 51, 1654 (2010).

    Article  CAS  Google Scholar 

  84. T. Wei, W. Zhu, J. Zhang, and H. Xiao, J. Hazard. Mater., 179, 581 (2010).

    Article  CAS  Google Scholar 

  85. A. S. Shawali and S. M. Elsheikh, J. Heterocycl. Chem., 38, 541 (2001).

    Article  CAS  Google Scholar 

  86. W. Adam, G. Goller, T. Kammel, and K. Peters, J. Org. Chem., 60, 308 (1995).

    Article  CAS  Google Scholar 

  87. E. Fahr, E. Buettner, K. H. Keil, J. Markert, F. Scheckenbach, R. Thiedemann, and J. Fontaine, Liebigs Ann. Chem., 1433 (1981).

  88. H. Wamhoff, H. W. Strobl, M. Jansen, and M. Ralle, Synthesis, 879 (1992).

  89. Yu. B. Koptelov, R. R. Kostikov, A. P. Molchanov, and Yu. Kopf, Zh. Org. Khim., 35, 149 (1999). [Russ. J. Org. Chem., 35, 144 (1999)].

    Google Scholar 

  90. Yu. S. Syroezhkina, V. V. Kuznetsov, K. A. Lysenko, and N. N. Makhova, Izv. Akad. Nauk, Ser. Khim., 362 (2009). [Russ. Chem. Bull., 58, 366 (2009)].

  91. Yu. B. Koptelov, Zh. Org. Khim., 42, 1524 (2006). [Russ. J. Org. Chem., 42, 1510 (2006)].

    Google Scholar 

  92. N. A. Lisowskaya, A. N. Maslivets, and Z. G. Aliev, Tetrahedron, 60, 5319 (2004).

    Article  CAS  Google Scholar 

  93. O. P. Krasnykh, N. A. Konyukhova, A. N. Maslivets, and Z. G. Aliev, RU Pat. Appl. 2233843.

  94. E. K. Y. Chen, M. Bancerz, G. K. Hamer, and M. K. Georges, Eur. J. Org. Chem., 5681 (2010).

  95. A. Yang, T. Kasahara, E. K. Y. Chen, G. K. Hamer, and M. K. Georges, Eur. J. Org. Chem., 4571 (2008).

  96. H. Neunhoeffer and H. J. Degen, Chem. Ber., 108, 3509 (1975).

    Article  CAS  Google Scholar 

  97. H. J. Degen, S. Haller, K. Heeg, and H. Neunhoeffer, Chem. Ber., 112, 1981 (1979).

    Article  CAS  Google Scholar 

  98. H. Neunhoeffer, U. Karafiat, G. Koehler, and B. Sowa, Liebigs Ann. Chem., 115 (1992).

  99. A. S. Shawali and N. M. Tawfik, Arch. Pharm. Res., 32, 975 (2009).

    Article  CAS  Google Scholar 

  100. D. G. Neilson, K. M. Watson, and T. R. Weakley, J. Chem. Soc., Perkin Trans. 1, 333 (1979).

  101. D. Hunter, D. G. Neilson, and T. J. R. Weakley, J. Chem. Soc., Perkin Trans. 1, 1165 (1982).

  102. L. Pellegatti, E. Vedrenne, J.-M. Leger, C. Jarry, and S. Routier, J. Comb. Chem., 12, 604 (2010).

    Article  CAS  Google Scholar 

  103. O. B. Bekker, V. N. Danilenko, R. I. Ishmetova, D. A. Maslov, G. L. Rusinov, S. G. Tolshchina, and V. N. Charushin, RU Pat. Appl. 2462466.

  104. H. Kumar and R. P. Chaudhary, J. Chem. Pharm. Res., 2, 667 (2010).

    CAS  Google Scholar 

  105. J. Mohan and D. Khatter, Indian. J. Heterocycl. Chem., 13, 323 (2004).

    CAS  Google Scholar 

  106. R. K. Behera, A. Pati, M. Patra, and A. K. Behera, Phosphorus, Sulfur Silicon Relat. Elem., 184, 2827 (2009).

    Article  CAS  Google Scholar 

  107. H. I. Tashtoush, F. Abusahyon, M. Shkoor, and M. Al-Talib, J. Sulf. Chem., 32, 405 (2011).

    Article  CAS  Google Scholar 

  108. A. Pati, S. Mohapatra, and R. K. Behera, J. Heterocycl. Chem., 48, 1234 (2011).

    Article  CAS  Google Scholar 

  109. V. R. Venkataraman and K. S. Ali, Ind. J. Heterocycl. Chem., 11, 93 (2001).

    CAS  Google Scholar 

  110. J. Mohan, Anjali, Indian J. Heterocycl. Chem., 15, 189 (2005).

    CAS  Google Scholar 

  111. J. Mohan, Shikha, Indian J. Heterocycl. Chem., 15, 187 (2005).

    CAS  Google Scholar 

  112. J. Mohan and A. Rathee, Indian J. Heterocycl. Chem., 15, 7 (2005).

    CAS  Google Scholar 

  113. J. Mohan, Indian J. Chem., Sect. B: Org. Chem. Incl. Med. Chem., 42B, 1460 (2003).

  114. J. Mohan, Indian J. Chem., Sect. B: Org. Chem. Incl. Med. Chem., 42B, 1176 (2003).

  115. J. Mohan and D. Khatter, Indian J. Heterocycl. Chem., 12, 169 (2002).

    CAS  Google Scholar 

  116. J. Mohan, Anupama, A. Kumar, and D. Khatter, Indian J. Chem., Sect. B: Org. Chem. Incl. Med. Chem., 41B, 400 (2002).

  117. J. Mohan, Anupama, A. Kumar, and D. Khatter, Indian J. Heterocycl. Chem., 10, 283 (2001).

  118. J. Mohan, Indian J. Chem., Sect. B: Org. Chem. Incl. Med. Chem., 40B, 584 (2001).

  119. V. R. Venkataraman and K. S. Ali, Indian J. Heterocycl. Chem., 10, 219 (2001).

    CAS  Google Scholar 

  120. J. Mohan and A. Kumar, Indian J. Heterocycl. Chem., 10, 89 (2000).

    CAS  Google Scholar 

  121. J. Mohan, Anupama, A. Kumar, and D. Khatter, Indian J. Heterocycl. Chem., 9, 251 (2000).

  122. V. A. Ershov and I. Ya. Postovskii, Khim. Geterotsikl. Soedin., 1134 (1968) [Chem. Heterocycl. Comp., 4, 826 (1968)].

    Google Scholar 

  123. R. G. Dickinson and N. W. Jacobsen, J. Chem. Soc., Perkin Trans. 1, 975 (1975).

  124. G. L. Rusinov, I. N. Ganebnykh, and O. N. Chupakhin, Zh. Org. Chem., 35, 1379 (1999). [Russ. J. Org. Chem., 35, 1350 (1999)].

    Google Scholar 

  125. D. E. Chavez and M. A. Hiskey, J. Heterocycl. Chem., 35, 1329 (1998).

    Article  CAS  Google Scholar 

  126. A. S. Shawali, A. N. Mosselhi, M. A. Abdallah, and M. S. Elewa, J. Chem. Res., 67 (2008).

  127. R. R. Kamble, B. S. Sudha, and D. B. Biradar, Ind. J. Heterocycl. Chem., 17, 121 (2007).

    CAS  Google Scholar 

  128. G. L. Rusinov, I. N. Ganebnykh, R. I. Ishmetova, N. K. Ignatenko, M. V. Berezin, S. G. Tolshchina, and A. V. Zolottseva, Vestn. UGTU-UPI, Ser. Khim., 57, No. 5, 158 (2005).

    Google Scholar 

  129. V. A. Ershov and I. Ya. Postovskii, Khim. Geterotsikl. Soedin., 708 (1971). [Chem. Heterocycl. Compd., 7, 665 (1971)].

    Google Scholar 

  130. I. N. Ganebnykh, S. G. Tolshchina, R. I. Ishmetova, N. K. Ignatenko, P. A. Slepukhin, G. L. Rusinov, and V. N. Charushin, Eur. J. Org. Chem., 2309 (2011).

  131. V. A. Ershov and I. Ya. Postovskii, Khim. Geterotsikl. Soedin., 711 (1971). [Chem. Heterocycl. Compd., 7, 668 (1971)].

    Google Scholar 

  132. H.-H. Licht and H. Ritter, J. Energ. Mat., 12, 223 (1994).

    Article  CAS  Google Scholar 

  133. A. Hammerl, T. M. Klapötke, and R. Rocha, Eur. J. Inorg. Chem., 2210 (2006).

Download references

Author information

Authors and Affiliations

  1. I. Ya. Postovskii Institute of Organic Synthesis, Ural Branch, Russian Academy of Sciences, 22 S. Kovalevskoi St. /20 Akademicheskaya St., Yekaterinburg, 620041, Russia

    S. G. Tolshchina, G. L. Rusinov & V. N. Charushin

Authors
  1. S. G. Tolshchina
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. G. L. Rusinov
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. V. N. Charushin
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to S. G. Tolshchina.

Additional information

Translated from Khimiya Geterotsiklicheskikh Soedinenii, pp. 75-101, January, 2013.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Tolshchina, S.G., Rusinov, G.L. & Charushin, V.N. 1,2,4,5-Tetrazines and Azolo[1,2,4,5]tetrazines: Synthesis and Reactions with Nucleophiles. Chem Heterocycl Comp 49, 66–91 (2013). https://doi.org/10.1007/s10593-013-1232-2

Download citation

  • Received:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s10593-013-1232-2

Keywords

Search

Navigation