Skip to main content
SpringerLink
Log in

Microwave synthesis of new azolyl-substituted thiazolo[5,4-d]thiazoles

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

Abstract

One-pot condensation of dithiooxamide with 4,5-dichloro-1,2-thiazole-3-carbaldehyde and 5-phenyl-1,2-oxazole-3-carbaldehyde, followed by oxidation of intermediate 2,5-dihydro[1,3]thiazolo[5,4-d]-[1,3]thiazoles with selenium dioxide, afforded previously unknown 2,5-bis(4,5-dichloro-1,2-thiazol-3-yl)- and 2,5-bis(5-phenyl-1,2-oxazol-3-yl)[1,3]thiazolo[5,4-d][1,3]thiazoles as first representative of bis-isothiazolyl- and bis-isoxazolyl thiazolothiazoles.

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. Reginato, G., Mordini, A., Zani, L., Calamante, M., and Dessì, A., Eur. J. Org. Chem., 2016, no. 2, p. 233.

    Article  Google Scholar 

  2. Bevk, D., Marin, L., Lutsen, L., Vanderzande, D., and Maes, W., RSC Adv., 2013, vol. 3, p. 11 418.

    Article  Google Scholar 

  3. Anthony, J.E., Angew. Chem., Int. Ed., 2008, vol. 47, p. 452.

    Article  CAS  Google Scholar 

  4. Peng, Q., Peng, J.B., Kang, E.T., Neoh, K.G., and Cao, Y., Macromolecules, 2005, vol. 38, p. 7292.

    Article  CAS  Google Scholar 

  5. Smirnova, N.G., Zavarzin, I.V., and Krayushkin, M.M., Chem. Heterocycl. Compd., 2006, vol. 42, p. 144.

    Article  CAS  Google Scholar 

  6. Jung, I.H., Jeong, J., Yu, E., Kim, J., Kwon, S., Kong, H., Lee, K., Woo, H.Y., and Shim, H.K., Chem. Eur. J., 2010, vol. 16, p. 3743.

    Article  CAS  Google Scholar 

  7. Osaka, I., Sauvé, G., Zhang, R., Kowalewski, T., and McCullough, R.D., Adv. Mater., 2007, vol. 19, p. 4160.

    Article  CAS  Google Scholar 

  8. Craft, A., Grimsdale, A.C., and Holmes, A.B., Angew. Chem., Int. Ed., 1998, vol. 37, p. 402.

    Article  Google Scholar 

  9. Ando, S., Nishida, J., Tada, H., Inoue, Y., Tokito, S., and Yamashita, Y., J. Am. Chem. Soc., 2005, vol. 127, p. 5336.

    Article  CAS  Google Scholar 

  10. Osaka, I., Zhang, R., Sauvé, G., Smilgies, D.-M., Kowalewski, T., and McCullough, R.D., J. Am. Chem. Soc., 2009, vol. 131, p. 2521.

    Article  CAS  Google Scholar 

  11. Knighton, R.C., Hallett, A.J., Kariuki, B.M., and Pope, S.J.A., Tetrahedron Lett., 2010, vol. 51, p. 5419.

    Article  CAS  Google Scholar 

  12. Pinto, M.R., Takahata, Y., and Atvars, T.D.Z., J. Photochem. Photobiol. A: Chem., 2001, vol. 143, p. 119.

    Article  CAS  Google Scholar 

  13. Zampese, J.A., Keene, F.R., and Steel, P.J., J. Chem. Soc., Dalton Trans., 2004, p. 4124.

    Google Scholar 

  14. Mortimer, S.G., Wells, G., Crochard, J.-P., Stone, E.L., Bradshaw, T.D., Stevens, M.F.G., and Westwell, A.D., J. Med. Chem., 2006, vol. 49, p. 179.

    Article  CAS  Google Scholar 

  15. Bradshaw, T.D. and Westwell, A.D., Curr. Med. Chem., 2004, vol. 11, p. 1009.

    Article  CAS  Google Scholar 

  16. Kini, G.D., Anderson, J.D., Sanghvi, Y.S., Lewis, A.F., Smee, D.F., Revankar, G.R., Robins, R.K., and Cottam, H.B., J. Med. Chem., 1991, vol. 34, p. 3006.

    Article  CAS  Google Scholar 

  17. Oketani, K., Inoue, T., and Murakami, M., Eur. J. Pharm., 2001, vol. 427, p. 159.

    Article  CAS  Google Scholar 

  18. Dessi, A., Calamante, M., Mordini, A., Zani, L., Taddei, M., and Reginato, G., RSC Adv., 2014, vol. 4, p. 1322.

    Article  CAS  Google Scholar 

  19. Maspero, A., Cernuto, G., Galli, S., Palmisano, G., Tollari, S., and Masciocchi, N., Solid State Sci., 2013, vol. 22, p. 43.

    Article  CAS  Google Scholar 

  20. Johnson, J.R. and Ketcham, R., J. Am. Chem. Soc., 1960, vol. 82, p. 2719.

    Article  CAS  Google Scholar 

  21. Ando, S., Kumaki, D., Nishida, J., Tada, H., Inoue, Y., Tokito, S., and Yamashita, Y.S., J. Mater. Chem., 2007, vol. 17, p. 553.

    Article  CAS  Google Scholar 

  22. Johnson, J.R., Rotenberg, D.H., and Ketcham, R., J. Am. Chem. Soc., 1970, vol. 92, p. 4046.

    Article  CAS  Google Scholar 

  23. Falcao, E.H.L., Feller, R.K., Wu, G., Wudl, F., and Cheetham, A.K., Inorg. Chem., 2008, vol. 47, no. 18, p. 8336.

    Article  CAS  Google Scholar 

  24. Mamada, M., Nishida, J., Kumaki, D., Tokito, S., and Yamashita, Y., Chem. Mater., 2007, vol. 19, p. 5404.

    Article  CAS  Google Scholar 

  25. Seybold, G. and Eilingsfeld, H., Justus Liebigs Ann. Chem., 1979, no. 9, p. 1271.

    Article  Google Scholar 

  26. Roethling, T., Schroeder, A., Kibbel, H., Kochmann, W., and Neumann, K., GDR Patent no. 210}457, 1984.

  27. Papernaya, L.K., Shatrova, A.A., Sterkhova, I.V., Levkovskaya, G.G., and Rozentsveig, I.B., Russ. J. Org. Chem., 2015, vol. 51, no. 3, p. 373.

    Article  CAS  Google Scholar 

  28. Shailaja, M., Manjula, A., and Vittal, R.B., Indian J. Chem., Sect. B, 2011, vol. 50, no. 2, p. 214.

    Google Scholar 

  29. Kulchitsky, V.A., Potkin, V.I., Zubenko, Yu.S., Chernov, A.N., Talabaev, M.V., Demidchik, Yu.E., Petkevich, S.K., Kazbanov, V.V., Gurinovich, T.A., Roeva, M.O., Grigoriev, D.G., Kletskov, A.V., and Kalunov, V.N., Med. Chem., 2012, vol. 8, no. 1, p. 22.

    Article  CAS  Google Scholar 

  30. Thumar, N.J. and Patel, M.P., Phosphorus, Sulfur Silicon Relat. Elem., 2009, vol. 184, no. 10, p. 2720.

    Article  CAS  Google Scholar 

  31. Shine, K., Tsemolka, Z., Kyunert, S., and Khaurand, M., RU Patent no. 2 450 010, 2012.

  32. Galenko, A.V., Khlebnikov, A.F., Novikov, M.S., Pakalnis, V.V., and Rostovskii, N.V., Russ. Chem. Rev., 2015, vol. 84, no. 4, p. 335.

    Article  CAS  Google Scholar 

  33. Pérez-Fernández, R., Goya, P., and Elguero, J., Arkivoc, 2014, part (ii), p. 233.

    Google Scholar 

  34. Gouhar, R.S. and Youns, M., Res. J. Pharm. Biol. Chem. Sci., 2014, vol. 5, p. 680.

    Google Scholar 

  35. Pizzuti, L., Barschak, A.G., Stefanello, F.M., Farias, M.D., Lencina, C., Roesch-Ely, M., Cunico, W., Moura, S., and Pereira, C.M.P., Curr. Org. Chem., 2014, vol. 18, p. 115.

    Article  CAS  Google Scholar 

  36. Potkin, V.I., Petkevich, S.K., Kletskov, A.V., Zubenko, Yu.S., Kurman, P.V., Pashkevich, S.G., Gurinovich, T.A., and Kul’chitskii, V.A., Russ. J. Org. Chem., 2014, vol. 50, no. 11, p. 1667.

    Article  CAS  Google Scholar 

  37. Potkin, V., Zubenko, Yu., Bykhovetz, A., Zolotar, R., and Goncharuk, V., Nat. Prod. Commun., 2009, vol. 4, p. 1205.

    CAS  Google Scholar 

  38. Potkin, V.I., Kletskov, A.V., Zubenko, Yu.S., Dikusar, E.A., Petkevich, S.K., Zvereva, T.D., Zolotar’, R.M., and Chepik, O.P., Dokl. Natl. Akad. Nauk Belarusi, 2013, vol. 57, no. 3, p. 76.

    CAS  Google Scholar 

  39. Papernaya, L.K., Shatrova, A.A., Albanov, A.I., Levkovskaya, G.G., and Rozentsveig, I.B., Arkivoc, 2016, part (v), p. 142.

    Google Scholar 

  40. Potkin, V.I., Petkevich, S.K., Kletskov, A.V., Dikusar, E.A., Zubenko, Yu.S., Zhukovskaya, N.A., Kazbanov, V.V., and Pashkevich, S.G., Russ. J. Org. Chem., 2013, vol. 49, no. 10, p. 1523.

    Article  CAS  Google Scholar 

  41. Bumagin, N.A., Zelenkovskii, V.M., Kletskov, A.V., Petkevich, S.K., Dikusar, E.A., and Potkin, V.I., Russ. J. Gen. Chem., 2016, vol. 86, no. 1, p. 68.

    Article  CAS  Google Scholar 

  42. Sheldrick, G.M., Acta Crystallogr., Sect. A, 2008, vol. 64, p. 112.

    Article  CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

  1. Favorskii Irkutsk Institute of Chemistry, Siberian Branch, Russian Academy of Sciences, ul. Favorskogo 1, Irkutsk, 664033, Russia

    L. K. Papernaya, A. A. Shatrova, I. V. Sterkhova, L. V. Klyba & G. G. Levkovskaya

  2. Institute of Physical Organic Chemistry, National Academy of Sciences of Belarus, ul. Surganova 13, Minsk, 220072, Belarus

    A. V. Kletskov & S. K. Petkevich

Authors
  1. L. K. Papernaya
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. A. A. Shatrova
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. A. V. Kletskov
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. S. K. Petkevich
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. I. V. Sterkhova
    View author publications

    You can also search for this author in PubMed Google Scholar

  6. L. V. Klyba
    View author publications

    You can also search for this author in PubMed Google Scholar

  7. G. G. Levkovskaya
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to L. K. Papernaya.

Additional information

Original Russian Text © L.K. Papernaya, A.A. Shatrova, A.V. Kletskov, S.K. Petkevich, I.V. Sterkhova, L.V. Klyba, G.G. Levkovskaya, 2017, published in Zhurnal Organicheskoi Khimii, 2017, Vol. 53, No. 4, pp. 545–551.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Papernaya, L.K., Shatrova, A.A., Kletskov, A.V. et al. Microwave synthesis of new azolyl-substituted thiazolo[5,4-d]thiazoles. Russ J Org Chem 53, 550–556 (2017). https://doi.org/10.1134/S107042801704008X

Download citation

  • Received:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1134/S107042801704008X

Search

Navigation