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Design and Characterization of l-Prolinate-Amberlite as a Novel Heterogeneous Organocatalyst and Its Catalytic Application in the Synthesis of Pyrazol-Derivates

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Abstract

The [Amb]l-prolinate obtained from the immobilization of l-prolinate anion onto amberlite IRA900OH, was used as a new organocatalyst for the efficient synthesis of 4,4′-(arylmethylene)-bis-(1H-pyrazol-5-ol) derivatives. The prepared heterogeneous organocatalyst was well characterized by using of FTIR, TGA, DTG, XRD and elemental analysis techniques. Short reaction times (5–18 min), excellent yields (82–98 %) and simple experimental procedure with an easy work-up are some of the advantages of the procedure.

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References

  1. Lancaster M (2002) Green chemistry: an introductory text. The Royal Society of Chemistry, Cambridge

    Google Scholar 

  2. Clark JH (2001) Pure Appl Chem 73:103–111

    Article  CAS  Google Scholar 

  3. Clark JH, Rhodes CN (2000) Clean synthesis using porous inorganic solid catalysts. RSC Clean Technology Monographs, Cambridge

    Google Scholar 

  4. Rajjak-Shaikh I (2014) J Catal 2014:1–35

    Article  Google Scholar 

  5. Gruttadauria M, Giacalone F, Noto R (2008) Chem Soc Rev 37:1666

    Article  CAS  Google Scholar 

  6. Cozzi F (2006) Adv Synth Catal 348:1367

    Article  CAS  Google Scholar 

  7. Ding K, Uozumi Y (eds) (2008) Handbook of asymmetric heterogeneous catalysis. Wiley-VCH, Weinhein

    Google Scholar 

  8. Bart ok M (2010) Chem Rev 110:1663-1705 Castillo´n Castillo´n

  9. Tsubogo T, Ishiwata T, Kobayashi S (2013) Angew Chem Int Ed 52:6590–6604

    Article  CAS  Google Scholar 

  10. Zhang L, Luo S, Cheng JP (2011) Catal Sci Technol 1:507–516

    Article  CAS  Google Scholar 

  11. Yamada SI, Otani G (1969) Tetrahedron Lett 10:4237–4240

    Article  Google Scholar 

  12. Shi F, Tan W, Zhu RY, Xing GJ, Tu SJ (2013) Adv Synth Catal 355:1605–1622

    Article  CAS  Google Scholar 

  13. Yang JW, Hechavarria Fonseca MT, List B (2005) J Am Chem Soc 127:15036–15037

    Article  CAS  Google Scholar 

  14. Bartok M (2015) Catal Rev Sci Eng 57:192–255

    Article  CAS  Google Scholar 

  15. Martín-Rapún R, Fan X, Sayalero S, Bahramnejad M, Cuevas F, Pericàs MA (2011) Chem Eur J 17:8780–8783

    Article  Google Scholar 

  16. Jimeno C, Sayalero S, Pericàs MA (2010) In: Barbaro P, Liguori F (eds) Heterogenized homogeneous catalysts for fine chemicals, vol 4. Springer, New York

  17. El-Sayed MA, Abdel-Aziz NI, Abdel-Aziz AA, El-Azab AS, El-Tahir KE (2012) Bioorg Med Chem 20:3306–3316

    Article  CAS  Google Scholar 

  18. Balbi A, Anzaldi M, Macciò C, Aiello C, Mazzei M, Gangemi R, Castagnola P, Miele M, Rosano C, Viale M (2011) Eur J Med Chem 46:5293–5309

    Article  CAS  Google Scholar 

  19. Rosiere CE, Grossman MI (1951) Science 113:651

    Article  CAS  Google Scholar 

  20. Bailey DM, Hansen PE, Hlavac AG, Baizman ER, Pearl J, Defelice AF, Feigenson ME (1985) J Med Chem 28:256–260

    Article  CAS  Google Scholar 

  21. Mahajan RN, Havaldar FH, Fernandes PS (1991) J Indian Chem Soc 68:245–246

    CAS  Google Scholar 

  22. Chauhan PMS, Singh S, Chatterjee RK (1993) Indian J Chem Sect B 32:858–861

    Google Scholar 

  23. Lubs HA (1970) The chemistry of synthetic dyes and pigments. American Chemical Society, Washington, DC

    Google Scholar 

  24. Londershausen M (1996) Pestic Sci 48:269

    Article  CAS  Google Scholar 

  25. Singh D, Singh DJ (1991) Indian Chem Soc 68:165

    CAS  Google Scholar 

  26. Garnovskii AD, Uraev AI, Minkin VI (2004) Arkivoc 3:29

    Google Scholar 

  27. Vafaee A, Davoodnia A, Pordel M (2015) Res Chem Intermed, Published online, 09 January

  28. Sadeghi B, Ghorbani M (2014) Iran J catal 4:67–70

    Google Scholar 

  29. Niknam K, Habibabad MS, Deris A, Aeinjamshid N (2014) Monatsh Chem 144:987–992

    Article  Google Scholar 

  30. Sobhani S, Pakdin-Parizi Z, Nasseri R (2013) J Chem Sci 125:975–979

    Article  CAS  Google Scholar 

  31. Parvanak-Boroujeni K, Shojaei P (2013) Turk J Chem 37:756–764

    Article  CAS  Google Scholar 

  32. Moosavi-Zare AR, Zolfigol MA, Zarei M, Zare A, Khakyzadeh V, Hasaninejad A (2013) Appl Catal A Gen 467:61–68

    Article  CAS  Google Scholar 

  33. Phatangare KR, Padalkar VS, Gupta VD, Patil VS, Umape PG, Sekar N (2012) Synth Commun 42:1349–1358

    Article  CAS  Google Scholar 

  34. Sobhani S, Hasaninejad AR, Faal-Maleki M, Pakdin-Parizi Z (2012) Synth Commun 42:2245–2255

    Article  CAS  Google Scholar 

  35. Hasaninejad A, Shekouhy M, Zare A, Hoseini-Ghattali SMS, Golzar N (2011) J Iran Chem Soc 8:411–423

    Article  CAS  Google Scholar 

  36. Suresh-Kuarm B, Rajitha B (2012) Synth Commun 42:2382–2387

    Article  Google Scholar 

  37. Gouda MA, Abu-Hashem AA (2012) Green Chem Lett Rev 5:203–209

    Article  CAS  Google Scholar 

  38. Khazaei A, Zolfigol MA, Moosavi-Zare AR, Asgari Z, Shekouhy M, Zare A, Hasaninejad A (2012) RSC Adv 2:8010–8013

    Article  CAS  Google Scholar 

  39. Tayebi S, Baghernejad M, Saberi D, Niknam K (2011) Chin J Catal 32:1477–1483

    Article  CAS  Google Scholar 

  40. Hasaninejad A, Zare A, Shekouhy M, Golzar N (2011) Org Prep Proced Int 43:131–137

    Article  CAS  Google Scholar 

  41. Niknam K, Saberi D, Sadegheyan M, Deris A (2010) Tetrahedron Lett 51:692–694

    Article  CAS  Google Scholar 

  42. Keshavarz M, Iravani N, Ghaedi A, ZareiAhmady A, Vafaei-Nezhad M, Karimi S (2013) Springerplus 2:64

    Article  Google Scholar 

  43. Albadi J, Keshavarz M (2013) Synth Commun 43:2019

    Article  CAS  Google Scholar 

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Acknowledgments

The authors gratefully acknowledge the Research Council of Yasouj University for financial support.

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Authors and Affiliations

  1. Department of Gas and Petroleum, Yasouj University, Gachsaran, Iran

    Mosadegh Keshavarz

  2. Department of Chemistry, Arak Branch, Islamic Azad University, Arak, Iran

    Masoumeh Vafaei-Nezhad

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  1. Mosadegh Keshavarz
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  2. Masoumeh Vafaei-Nezhad
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Correspondence to Mosadegh Keshavarz.

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Keshavarz, M., Vafaei-Nezhad, M. Design and Characterization of l-Prolinate-Amberlite as a Novel Heterogeneous Organocatalyst and Its Catalytic Application in the Synthesis of Pyrazol-Derivates. Catal Lett 146, 353–363 (2016). https://doi.org/10.1007/s10562-015-1668-3

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  • DOI: https://doi.org/10.1007/s10562-015-1668-3

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