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Convenient regioselective reaction in presence of H3PW12O40: synthesis and characterization of pyrazolo[3,4-b]quinoline-3,5-diones

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Abstract

We describe regioselective synthesis of pyrazolo[3,4-b]quinoline derivatives by multicomponent reaction of dimedone, 5-aminopyrazolone, and aromatic aldehydes in presence of H3PW12O40 as catalyst. When this multicomponent reaction was investigated without catalyst under reflux conditions, a mixture of products was obtained, while the reaction successfully proceeded to formation of pyrazolo[3,4-b]quinoline in presence of H3PW12O40. Good product yield, short experimental time, and low-cost catalyst provide convenient synthesis for formation of pyrazolo[3,4-b]quinoline pharmacological compounds.

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References

  1. T. Ueda, H. Mase, N. Oda, I. Ito, Chem. Pharm. Bull. 29, 3522 (1981)

    Article  CAS  Google Scholar 

  2. C. Malvar Ddo, R.T. Ferreira, R.A. de Castro, L.L. de Castro, A.C. Freitas, E.A. Costa, I.F. Florentino, J.C. Mafra, G.E. de Souza, F.A. Vanderlinde, Life Sci. 95, 81 (2014)

    Article  Google Scholar 

  3. M. Sanchez-Moreno, C. Marin, P. Navarro, L. Lamarque, E. Garcia-Espana, C. Miranda, O. Huertas, F. Olmo, F. Gomez-Contreras, J. Pitarch, F. Arrebola, J. Med. Chem. 55, 4231 (2012)

    Article  CAS  Google Scholar 

  4. X. Fan, X. Zhang, L. Zhou, K.A. Keith, E.R. Kern, P.F. Torrence, Bioorg. Med. Chem. Lett. 16, 3224 (2006)

    Article  CAS  Google Scholar 

  5. S.-L. Wang, Y.P. Liu, B.H. Xu, X.H. Wang, B. Jiang, S.J. Tu, Tetrahedron 67, 9417 (2011)

    Article  CAS  Google Scholar 

  6. W. Anna, B. Lilianna, Mini Rev. Org. Chem. 12, 298 (2015)

    Article  Google Scholar 

  7. S.T. Selvi, V. Nadaraj, S. Mohan, R. Sasi, M. Hema, Bioorg. Med. Chem. 14, 3896 (2006)

    Article  CAS  Google Scholar 

  8. A. Kamal, J.R. Tamboli, V.L. Nayak, S.F. Adil, M.V. Vishnuvardhan, S. Ramakrishna, Bioorg. Med. Chem. Lett. 23, 3208 (2013)

    Article  CAS  Google Scholar 

  9. S. Taliani, I. Pugliesi, E. Barresi, S. Salerno, C. Marchand, K. Agama, F. Simorini, C. La Motta, A.M. Marini, F.S. Di Leva, L. Marinelli, S. Cosconati, E. Novellino, Y. Pommier, R. Di Santo, F. Da Settimo, J. Med. Chem. 56, 7458 (2013)

    Article  CAS  Google Scholar 

  10. R.L. Siegel, K.D. Miller, A. Jemal, CA Cancer J. Clin. 66, 7 (2016)

    Article  Google Scholar 

  11. S. Rádl, V. Zikán, F. Šmejkal, Collect. Czech. Chem. Commun. 50, 1057 (1985)

    Article  Google Scholar 

  12. P. Siminoff, R.R. Crenshaw, Antimicrob. Agents Chemother. 11, 571 (1977)

    Article  CAS  Google Scholar 

  13. R.G. Stein, J.H. Biel, T. Singh, J. Med. Chem. 13, 153 (1970)

    Article  CAS  Google Scholar 

  14. P.K. Sharma, K. Singh, S. Kumar, P. Kumar, S.N. Dhawan, S. Lal, H. Ulbrich, G. Dannhardt, Med. Chem. Res. 20, 239 (2011)

    Article  CAS  Google Scholar 

  15. C. Kalinski, H. Lemoine, J. Schmidt, C. Burdack, J. Kolb, M. Umkehrer, G. Ross, Synthesis 2008, 4007 (2008)

    Article  Google Scholar 

  16. I. Ugi, A. Dömling, W. Hörl, Endeavour 18, 115 (1994)

    Article  CAS  Google Scholar 

  17. J.E. Biggs-Houck, A. Younai, J.T. Shaw, Curr. Opin. Chem. Biol. 14, 371 (2010)

    Article  CAS  Google Scholar 

  18. T. Zarganes-Tzitzikas, A.L. Chandgude, A. Domling, Chem. Rec. 15, 981 (2015)

    Article  CAS  Google Scholar 

  19. M. Manpadi, P.Y. Uglinskii, S.K. Rastogi, K.M. Cotter, Y.S. Wong, L.A. Anderson, A.J. Ortega, S. Van Slambrouck, W.F. Steelant, S. Rogelj, P. Tongwa, M.Y. Antipin, I.V. Magedov, A. Kornienko, Org. Biomol. Chem. 5, 3865 (2007)

    Article  CAS  Google Scholar 

  20. P. Acosta, E. Butassi, B. Insuasty, A. Ortiz, R. Abonia, S.A. Zacchino, J. Quiroga, Molecules 20, 8499 (2015)

    Article  CAS  Google Scholar 

  21. V.A. Chebanov, V.E. Saraev, S.M. Desenko, V.N. Chernenko, I.V. Knyazeva, U. Groth, T.N. Glasnov, C.O. Kappe, J. Org. Chem. 73, 5110 (2008)

    Article  CAS  Google Scholar 

  22. M. Zahedifar, H. Sheibani, Chem. Heterocycl. Compd. 52, 41 (2016)

    Article  CAS  Google Scholar 

  23. M. Zahedifar, H. Sheibani, Aust. J. Chem. 67, 1201 (2014)

    CAS  Google Scholar 

  24. H. Sheibani, V. Saheb, M. Rezaei, M. Zahedifar, Lett. Org. Chem. 11, 126 (2014)

    Article  CAS  Google Scholar 

  25. M. Zahedifar, H. Sheibani, Res. Chem. Intermed. 41, 105 (2013)

    Article  Google Scholar 

  26. M. Zahedifar, R. Razavi, H. Sheibani, J. Mol. Struct. 1125, 730 (2016)

    Article  CAS  Google Scholar 

  27. F. Alinaghizadeh, M. Zahedifar, M. Seifi, H. Sheibani, J. Braz. Chem. Soc. 27, 663 (2016)

    CAS  Google Scholar 

  28. M. Abaszadeh, H. Sheibani, K. Saidi, Aust. J. Chem. 63, 92 (2010)

    Article  CAS  Google Scholar 

  29. I. Drizin, R.J. Altenbach, S.A. Buckner, K.L. Whiteaker, V.E. Scott, J.F. Darbyshire, V. Jayanti, R.F. Henry, M.J. Coghlan, M. Gopalakrishnan, W.A. Carroll, Bioorg. Med. Chem. 12, 1895 (2004)

    Article  CAS  Google Scholar 

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Acknowledgements

The authors express appreciation to the University of Jiroft Faculty Research Committee and Shahid Bahonar University of Kerman for supporting this investigation. This research was supported by the University of Jiroft under grant no. 95-3813-3.

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Authors and Affiliations

  1. Department of Chemistry, Faculty of Science, University of Jiroft, Jiroft, 7867161167, Iran

    Mahboobeh Zahedifar

  2. Department of Chemistry, Shahid Bahonar University of Kerman, Kerman, 76169, Iran

    Reza Shojaei & Hassan Sheibani

Authors
  1. Mahboobeh Zahedifar
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  2. Reza Shojaei
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  3. Hassan Sheibani
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Correspondence to Mahboobeh Zahedifar.

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Zahedifar, M., Shojaei, R. & Sheibani, H. Convenient regioselective reaction in presence of H3PW12O40: synthesis and characterization of pyrazolo[3,4-b]quinoline-3,5-diones. Res Chem Intermed 44, 873–882 (2018). https://doi.org/10.1007/s11164-017-3141-y

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  • DOI: https://doi.org/10.1007/s11164-017-3141-y

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