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An eco-compatible, three-component synthesis of acyl-substituted bis(pyrazolyl)methanes by employing recyclable silica sodium carbonate as an efficient and environmentally benign catalyst in aqueous medium

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Abstract

In this work, an efficient and green protocol for the synthesis of newly prepared acyl-substituted bis(pyrazolyl)methane derivatives has been introduced via a one-pot, three-component (2 + 1) condensation reaction by the use of 3-methyl-1-phenyl-2-pyrazolin-5-one, arylglyoxal derivatives, and silica sodium carbonate (SSC) as a recyclable green catalyst. All synthesized products were obtained with good to excellent yields, and their structures were deduced by FT-IR, 1H NMR, 13C NMR spectroscopies, and (C, H, N, S) elemental analyses. The capability of SSC to be reused can be considered as one of this procedure’s advantages. The studies on the reusability of catalyst revealed that SSC can efficiently catalyze this condensation reaction up to six times without significant loss of activity.

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References

  1. Eftekhari-Sis B, Zirak M, Akbari A (2013) Chem Rev 113:2958

    Article  CAS  PubMed  Google Scholar 

  2. Farahi M, Karami B, Banaki Z, Rastgoo F, Eskandari K (2017) Monatsh Chem 148:1469

    Article  CAS  Google Scholar 

  3. Khodabakhshi S, Karami B, Eskandari K (2014) Heterocycles 89:1670

    Article  CAS  Google Scholar 

  4. Khodabakhshi S, Karami B, Eskandari K, Farahi M (2014) Tetrahedron Lett 55:3753

    Article  CAS  Google Scholar 

  5. Khodabakhshi S, Karami B, Eskandari K, Hoseini SJ, Nasrabadi H (2017) Arab J Chem 10:S3907

    Article  CAS  Google Scholar 

  6. Eskandari K, Karami B, Farahi M, Mouzari V (2016) Tetrahedron Lett 57:487

    Article  CAS  Google Scholar 

  7. Karami B, Eskandari K, Azizi M (2013) Lett Org Chem 10:722

    Article  CAS  Google Scholar 

  8. Karami B, Eskandari K, Khodabakhshi S, Hoseini SJ, Hashemian F (2013) RSC Adv 3:23335

    Article  CAS  Google Scholar 

  9. Clark JH (2002) Acc Chem Res 35:791

    Article  CAS  PubMed  Google Scholar 

  10. Zarganes-Tzitzikas T, Terzidis MA, Stephanidou-Stephanatou J, Tsoleridis A, Kostakis GE (2011) J Org Chem 76:9008

    Article  CAS  PubMed  Google Scholar 

  11. Carney DW, Truong JV, Sello JK (2011) J Org Chem 76:10279

    Article  CAS  PubMed  Google Scholar 

  12. Hulme C, Gore V (2003) Curr Med Chem 1:51

    Article  Google Scholar 

  13. Ramon DJ, Yus M (2005) Angew Chem Int Ed 44:1602

    Article  CAS  Google Scholar 

  14. Habibi A, Eskandari K, Alizadeh A (2012) Phosphorus. Sulfur Silicon Relat Elem 187:1109

    Article  CAS  Google Scholar 

  15. Li C-J, Chan T-H (2007) Comprehensive organic reactions in aqueous media, 2nd edn. Wiley, Hoboken, p 65

    Book  Google Scholar 

  16. Karami B, Hoseini SJ, Eskandari K, Ghasemi A, Nasrabadi H (2012) Catal Sci Technol 2:331

    Article  CAS  Google Scholar 

  17. Dicks AP (2009) Green Chem Lett Rev 2:9

    Article  CAS  Google Scholar 

  18. Santi C, Jacob RG, Monti B, Bagnoli L, Sancineto L, Lenardão EJ (2016) Molecules 21:1482

    Article  CAS  Google Scholar 

  19. Karami B, Eskandari K, Zare Z, Gholipour S (2014) Chem Heterocycl Compd 49:1715

    Article  CAS  Google Scholar 

  20. Poorali L, Karami B, Eskandari K, Azizi M (2013) J Chem Sci 125:591

    Article  CAS  Google Scholar 

  21. Karami B, Ferdosian R, Eskandari K (2014) J Chem Res 38:41

    Article  CAS  Google Scholar 

  22. Eskandari K, Karami B, Khodabakhshi S, Farahi M (2015) Lett Org Chem 12:38

    Article  CAS  Google Scholar 

  23. Eskandari K, Karami B (2016) Comb Chem High Throughput Screen 19:728

    Article  CAS  PubMed  Google Scholar 

  24. Eskandari K, Karami B, Khodabakhshi S (2014) Catal Commun 54:124

    Article  CAS  Google Scholar 

  25. Shinde VV, Reddy MV, Kim YH, Cho BK, Jeong YT (2015) Monatsh Chem 146:673

    Article  CAS  Google Scholar 

  26. Eskandari K, Karami B (2016) Curr Green Chem 3:168

    Article  CAS  Google Scholar 

  27. Karami B, Farahi M, Banaki Z (2015) Synlett 26:1804

    Article  CAS  Google Scholar 

  28. Wu X, Geng X, Zhao P, Wu Y, Wu A (2017) Org Lett 19:4584

    Article  CAS  PubMed  Google Scholar 

  29. Tayebi S, Baghernejad M, Saberi D, Niknam K (2011) Chin J Catal 32:1477

    Article  CAS  Google Scholar 

  30. Mosaddegh E, Hassankhani A, Baghizadeh A (2010) J Chil Chem Soc 55:419

    Article  CAS  Google Scholar 

  31. Sobhani S, Nasseri R, Honarmand M (2012) Can J Chem 90:798

    Article  CAS  Google Scholar 

  32. Khazaei A, Zolfigol MA, Moosavi-Zare AR, Asgari Z, Shekouhy M, Zare A, Hasaninejad A (2012) RSC Adv 2:8010

    Article  CAS  Google Scholar 

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Acknowledgements

The authors would like gratefully to thank the Yasouj University Research Council for their partial support in this work.

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Correspondence to Khalil Eskandari.

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Eskandari, K., Karami, B., Pourshojaei, Y. et al. An eco-compatible, three-component synthesis of acyl-substituted bis(pyrazolyl)methanes by employing recyclable silica sodium carbonate as an efficient and environmentally benign catalyst in aqueous medium. Monatsh Chem 149, 1075–1081 (2018). https://doi.org/10.1007/s00706-017-2106-6

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  • DOI: https://doi.org/10.1007/s00706-017-2106-6

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