Chemistry of Heterocyclic Compounds

, Volume 49, Issue 2, pp 350–352 | Cite as

Synthesis of condensed [1,2,3]triazolo-[5,1-b][1,3,4]thiadiazepine systems

  • T. A. Kalinina
  • D. V. Shatunova
  • T. V. Glukhareva
  • Yu. Yu. Morzherin
In contemporary organic chemistry, rearrangements and transformations of one type of heterocycle to another are promising and convenient methods for the preparation of heterocyclic structures difficult to obtain by other means. However, these reactions are rarely used as a planned method for preparing heterocyclic systems. 1,2,3-Thiadiazoles are convenient starting materials for carrying out various rearrangements. Several rearrangements of 1,2,3-thiadiazoles involving a substituent in the ring position 5 are known [ 1, 2, 3], but only a few of these lead to the preparation of condensed 1,2,3-triazoles. Thus, for example, methods are known for the synthesis of [1,2,3]triazolo[5,1- b][1,3,4]thiadiazines using the Dimroth rearrangement [ 4, 5].


pyrazoles quinolines 1,3,4-thiadiazepines 1,2,3-thiadiazoles 1,2,3-triazoles Dimroth rearrangement 


  1. 1.
    Yu. Yu. Morzherin, T. V. Glukhareva, and V. A. Bakulev, Khim. Geterotsikl. Soedin., 803 (2003). [Chem. Heterocycl. Compd., 39, 679 (2003)].Google Scholar
  2. 2.
    A. A. Shchipalkin, M. L. Petrov, and V. A. Kuznetsov, Zh. Org. Khim., 47, 1191 (2011). [Russ. J. Org. Chem., 47, 1209 (2011)].Google Scholar
  3. 3.
    T. A. Kalinina, P. E. Prokhorova, T. V. Glukhareva, and Yu. Yu. Morzherin, Izv. Akad. Nauk, Ser. Khim., 957 (2011). [Russ. Chem. Bull., Int. Ed., 60, 981 (2011)].Google Scholar
  4. 4.
    G. L′Abbé and E. Vanderstede, J. Heterocycl. Chem., 26, 1811 (1989).CrossRefGoogle Scholar
  5. 5.
    Y. Y. Morzherin, T. V. Glukhareva, I. N. Slepukhina, V. S. Mokrushin, A. V. Tkachev, and V. A. Bakulev, Mendeleev Commun., 10, 19 (2000).CrossRefGoogle Scholar
  6. 6.
    O. Meth-Cohn and D. L. Taylor, Tetrahedron, 47, 12869 (1995).CrossRefGoogle Scholar
  7. 7.
    B. Datterl, N. Tröstner, D. Kucharski, and W. Holzer, Molecules, 15, 6106 (2010).CrossRefGoogle Scholar
  8. 8.
    B. Prabhuswamy and S. Y. Ambekar, Synth. Commun., 29, 3487 (1999).CrossRefGoogle Scholar
  9. 9.
    J. J. Vora, D. R. Patel, N. V. Bhimani, and P. V. Ajudia, J. Chil. Chem. Soc., 56, 771 (2011).CrossRefGoogle Scholar
  10. 10.
    B. Kalluraya, R. Gururaja, and G. Rai, Indian J. Chem., Sect. B, 42, 211 (2003).Google Scholar
  11. 11.
    M. Gupta, S. Paul, and R. Gupta, Indian J. Chem., Sect. B, 48, 460 (2009).Google Scholar

Copyright information

© Springer Science+Business Media New York 2013

Authors and Affiliations

  • T. A. Kalinina
    • 1
  • D. V. Shatunova
    • 1
  • T. V. Glukhareva
    • 1
  • Yu. Yu. Morzherin
    • 1
  1. 1.Ural Federal University named after the First President of Russia B. N. YeltsinYekaterinburgRussia

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