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One-pot sequential double annulations cascade reaction for imidazo[1,2-b]pyrazoles synthesis

  • Shokoufe Goli
  • Peiman Mirzaei
  • Ayoob Bazgir
Original Paper

Abstract

We have developed efficient and green methods for the synthesis of imidazo[1,2-b]pyrazole derivatives by Groebke–Blackburn–Bienaymé (GBB) reaction of 5-aminopyrazole, aldehyde and trimethylsilyl cyanid under thermal condition in 1-n-butyl-3-methylimidazolium tetrafluoroborate [Bmim]BF4 ionic liquid. A one-pot sequential double annulation cascade reaction has also been demonstrated for imidazo[1,2-b]pyrazoles synthesis.

Graphical abstract

Keywords

Imidazo[1,2-b]pyrazoles GBB reaction [Bmim]BF4 Sequential reaction One-pot synthesis 

Notes

Acknowledgements

We gratefully acknowledge the financial support from the Research Council of Shahid Beheshti University and the Iran National Science Foundation (INSF) for the financial support of this work.

References

  1. 1.
    S. Sadjadi, M.M. Heravi, N. Nazari, RSC Adv. 6, 53203 (2016)CrossRefGoogle Scholar
  2. 2.
    A. Váradi, T.C. Palmer, R.N. Dardashti, S. Majumdar, Molecules 21, 19 (2016)CrossRefGoogle Scholar
  3. 3.
    A. Dömling, I. Ugi, Angew. Chem. Int. Ed. 40, 2224 (2001)CrossRefGoogle Scholar
  4. 4.
    A. Shaabani, A. Maleki, A.H. Rezayan, A. Sarvary, Mol. Divers. 15, 41 (2011)CrossRefGoogle Scholar
  5. 5.
    Y.M. Yan, Y. Rao, M.W. Ding, J. Org. Chem. 82, 2772 (2017)CrossRefGoogle Scholar
  6. 6.
    M. Krasavin, S. Shkavrov, V. Parchinsky, K. Bukhryakov, Org. Chem. 74, 2627 (2009)CrossRefGoogle Scholar
  7. 7.
    L. Wang, Z.R. Guana, M.W. Ding, Org. Biomol. Chem. 14, 2413 (2016)CrossRefGoogle Scholar
  8. 8.
    S. Balalaie, M. Shamakli, A. Nikbakht, N.S. Alavijeh, F. Rominger, S. Rostamizadeha, H.R. Bijanzadeh, Org. Biomol. Chem. 15, 5737 (2017)CrossRefGoogle Scholar
  9. 9.
    S.K. Guchhait, V. Chaudhary, C. Madaan, Org. Biomol. Chem. 10, 9271 (2012)CrossRefGoogle Scholar
  10. 10.
    G. Martinez-Ariza, M. Ayaz, F. Medda, C. Hulme, J. Org. Chem. 79, 5153 (2014)CrossRefGoogle Scholar
  11. 11.
    T. Kaur, D. Saha, N. Singh, U.P. Singh, A. Sharma, Chem. Select. 3, 434 (2016)Google Scholar
  12. 12.
    T. Kaur, R.N. Gautam, A. Sharma, Chem. Asian J. 11, 2938 (2016)CrossRefGoogle Scholar
  13. 13.
    S. Shaaban, B.F. Abdel-Wahab, Mol. Divers. 20, 233 (2016)CrossRefGoogle Scholar
  14. 14.
    S.K. Guchhait, C. Madaan, Tetrahedron Lett. 52, 56 (2011)CrossRefGoogle Scholar
  15. 15.
    I. Akritopoulou-Zanze, B.D. Wakefield, A. Gasiecki, D. Kalvin, E.F. Johnson, P. Kovar, S.W. Djuric, Bioorg. Med. Chem. Lett. 21, 1480 (2011)CrossRefGoogle Scholar
  16. 16.
    A.T. Baviskar, C. Madaan, R. Preet, P. Mohapatra, V. Jain, A. Agarwal, S.K. Guchhait, C.N. Kundu, U.C. Banerjee, P.V. Bharatam, J. Med. Chem. 54, 5013 (2011)CrossRefGoogle Scholar
  17. 17.
    J. Schwerkoske, T. Masquelin, T. Perun, C. Hulme, Tetrahedron Lett. 46, 8355 (2005)CrossRefGoogle Scholar
  18. 18.
    T. Masquelin, H. Bui, B. Brickley, G. Stephenson, J. Schwerkoske, C. Hulme, Tetrahedron Lett. 47, 2989 (2006)CrossRefGoogle Scholar
  19. 19.
    E. Bell, A.Y. Shaw, F. De Moliner, C. Hulme, Tetrahedron 70, 54 (2014)CrossRefGoogle Scholar
  20. 20.
    A.I. Polyakov, V.A. Eryomina, L.A. Medvedeva, N.I. Tihonova, A.V. Listratova, L.G. Voskressensky, Tetrahedron Lett. 50, 4389 (2009)CrossRefGoogle Scholar
  21. 21.
    A. Shaabani, A. Maleki, Monatsh. Chem. 138, 51 (2007)CrossRefGoogle Scholar
  22. 22.
    F. Chen, M. Lei, L. Hu, Tetrahedron 69, 2954 (2013)CrossRefGoogle Scholar
  23. 23.
    M. Abdollahi-Alibeik, A. Rezaeipoor-Anari, Catal. Sci. Technol. 4, 1151 (2014)CrossRefGoogle Scholar
  24. 24.
    A.O. Abdelhamid, E.K.A. Abdelall, Y.H. Zakic, J. Heterocycl. Chem. 47, 477 (2010)Google Scholar
  25. 25.
    S. Grosse, V. Mathieu, C. Pillard, S. Massip, M. Marchivied, C. Jarry, P. Bernard, R. Kiss, G. Guillaumet, Eur. J. Med. Chem. 84, 718 (2014) (and references sited therein).CrossRefGoogle Scholar
  26. 26.
    A. Terada, K. Wachi, H. Myazawa, Y. Lizuka, K. Hagesawa, K. Tabata, Japanese Patent JP 07278148 (1995), Chem. Abst. 124, 8700 (1996)Google Scholar
  27. 27.
    T. Baviskar, C. Madaan, R. Preet, P. Mohapatra, V. Jain, A. Agarwal, S.K. Guchhait, C.N. Kundu, U.S. Banerjee, P.V. Bharatam, J. Med. Chem. 54, 5013 (2011)CrossRefGoogle Scholar
  28. 28.
    G. Bhatia, P. Graczyk, A. Khan, D.P. Medland, H. Numata, H. Oinuma, V. Palmer, International Patent 310918 (2002). WO02081475 (A1) Chem. Abst. 137 (2002)Google Scholar
  29. 29.
    B. Frey, R. Hufton, M. Harding, A.G. Draffan, International Patent 446979 (2013). WO2013036994, Chem. Abst. 158 (2013)Google Scholar
  30. 30.
    K. Sata, T. Kawagishi, H. Kobayashi, Jpn. Kokai Tokyo 07,134,380(1995), Chem. Abst. 123, 183329q (1995)Google Scholar
  31. 31.
    J. Bailey, D. Rogers, WO 8602467 (1986), Chem. Abst. 105, 143476 (1986)Google Scholar
  32. 32.
    A. Barsy, E.A. El-Rady, J. Heterocycl. Chem. 43, 523 (2006)CrossRefGoogle Scholar
  33. 33.
    J. Khalafy, A. Poursattar Marjani, F. Salami, Tetrahedron Lett. 55, 6671 (2014)CrossRefGoogle Scholar
  34. 34.
    A. Rahmati, M. Eskandari-Vashareh, M. Alizadeh-Kouzehrash, Tetrahedron Lett. 69, 4199 (2013)CrossRefGoogle Scholar
  35. 35.
    A. Rahmati, M. Alizadeh-Kouzehrash, Synthesis 2011, 2913 (2011)CrossRefGoogle Scholar
  36. 36.
    S. Shawali, M.H. Abdelkader, M.A. Eltalbawy, Tetrahedron 58, 2875 (2002)CrossRefGoogle Scholar
  37. 37.
    E. Vanotti, F. Fiorentini, M. Villa, J. Heterocycl. Chem. 31, 737 (1994)CrossRefGoogle Scholar
  38. 38.
    L. Moafi, S. Ahadi, A. Bazgir, Tetrahedron Lett. 51, 6270 (2010)CrossRefGoogle Scholar
  39. 39.
    R. Akbarzadeh, T. Amanpour, A. Bazgir, Tetrahedron Lett. 70, 8142 (2014)CrossRefGoogle Scholar
  40. 40.
    Y. Tominaga, Y. Honkawa, M. Hara, A. Hosomi, J. Heterocycl. Chem. 27, 775 (1990)CrossRefGoogle Scholar
  41. 41.
    K. Groebke, L. Weber, F. Mehlin, Synlett 1998, 661 (1998)CrossRefGoogle Scholar
  42. 42.
    H. Bienayme, K. Bouzid, Angew. Chem. 110, 2349 (1998)CrossRefGoogle Scholar

Copyright information

© Iranian Chemical Society 2018

Authors and Affiliations

  1. 1.Department of ChemistryShahid Beheshti UniversityTehranIran

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