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A rapid, efficient, and high-yielding synthesis of 4,4′-(arylmethylene)bis(3-methyl-1H-pyrazol-5-ol) derivatives catalyzed by 12-tungstophosphoric acid (H3PW12O40)

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Abstract

A fast, green, and efficient method for high-yielding synthesis of 4,4′-(arylmethylene)bis(3-methyl-1H-pyrazol-5-ols) by one-pot reaction of two equivalents of 3-methyl-1H-pyrazol-5(4H)-one with aryl aldehydes, using 12-tungstophosphoric acid (H3PW12O40) as an effective and inorganic catalyst is described. The catalyst is inexpensive and readily available and can be recovered conveniently and reused efficiently such that a considerable catalytic activity still could be achieved after the tenth run. Compared to the other methods, the present methodology offers several advantages such as excellent yields, short reaction times, and mild reaction conditions with an easy work-up.

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References

  1. N. Uramaru, H. Shigematsu, A. Toda, R. Eyanagi, S. Kitamura, S. Ohta, J. Med. Chem. 53, 8727 (2010)

    Article  CAS  Google Scholar 

  2. D.M. Bailey, P.E. Hansen, A.G. Hlavac, E.R. Baizman, J. Pearl, A.F. Defelice, M.E. Feigenson, J. Med. Chem. 28, 256 (1985)

    Article  CAS  Google Scholar 

  3. K. Sujatha, G. Shanthi, N.P. Selvam, S. Manoharan, P.T. Perumal, M. Rajendran, Bioorg. Med. Chem. Lett. 19, 4501 (2009)

    Article  CAS  Google Scholar 

  4. D. Singh, D. Singh, J. Indian Chem. Soc. 68, 165 (1991)

    CAS  Google Scholar 

  5. J.J. Liu, M.Y. Zhao, X. Zhang, X. Zhao, H.L. Zhu, Mini Rev. Med. Chem. 13, 1957 (2013)

    Article  CAS  Google Scholar 

  6. S. Sugiura, S. Ohno, O. Ohtani, K. Izumi, T. Kitamikado, H. Asai, K. Kato, M. Hori, H. Fujimura, J. Med. Chem. 20, 80 (1977)

    Article  CAS  Google Scholar 

  7. Y. Liu, G. He, C. Kai, Y. Li, H. Zhu, J. Heterocycl. Chem. 49, 1370 (2012)

    Article  CAS  Google Scholar 

  8. M. Londershausen, Pestic. Sci. 48, 269 (1996)

    Article  CAS  Google Scholar 

  9. R.C. Maurya, R. Verma, Indian J. Chem. Sect. A 36, 596 (1997)

    Google Scholar 

  10. A.D. Garnovskii, A.I. Uraev, V.I. Minkin, Arkivoc 3, 29 (2004)

    Google Scholar 

  11. H. Nakagawa, R. Ohyama, A. Kimata, T. Suzuki, N. Miyata, Bioorg. Med. Chem. Lett. 16, 5939 (2006)

    Article  CAS  Google Scholar 

  12. P. Kessler, T. Aybek, G. Neidhart, S. Dogan, D.H. Bremerich, V. Lischke, C. Byhahan, J. Cardiothorac. Vasc. Anesth. 19, 32 (2005)

    Article  Google Scholar 

  13. M.Z. Wisniewski, W.J. Surga, E.M. Opozda, Transit. Met. Chem. 19, 353 (1994)

    Article  CAS  Google Scholar 

  14. M. F. El-Shehry, E. M. El-Telbani, R. H. Swellem, J. Chem. Res. 33, 625 (2009)

  15. W.S. Hamama, Synth. Commun. 31, 1335 (2001)

    Article  CAS  Google Scholar 

  16. M. Bortoluzzi, G. Paolucci, B. Pitteri, A. Vavasori, V. Bertolasi, Organometallics 28, 3247 (2009)

    Article  CAS  Google Scholar 

  17. X.L. Li, Y.M. Wang, B. Tian, T. Matsuura, J.B. Meng, J. Heterocycl. Chem. 35, 129 (1998)

    Article  CAS  Google Scholar 

  18. Z. Karimi-Jaberi, B. Pooladian, M. Moradi, E. Ghasemi, Chin. J. Catal. 33, 1945 (2012)

    Article  CAS  Google Scholar 

  19. S. Sobhani, A.R. Hasaninejad, M. Faal, Z. Maleki, P. Parizi, Synth. Commun. 42, 2245 (2012)

    Article  CAS  Google Scholar 

  20. M. Baghernejad, K. Niknam, Int. J. Chem. 4, 52 (2012)

    Article  CAS  Google Scholar 

  21. S. Tayebi, K. Niknam, Iranian. J. Catal. 2, 69 (2012)

    CAS  Google Scholar 

  22. Z. Zhou, Y. Zhang, Green Chem. Lett. Rev. 7, 18 (2014)

    Article  Google Scholar 

  23. W. Wang, S.X. Wang, X.Y. Qin, J.T. Li, Synth. Commun. 35, 1263 (2005)

    Article  CAS  Google Scholar 

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

    Article  CAS  Google Scholar 

  25. A. Hasaninejad, M. Shekouhy, A. Zare, S.M.S. Hoseini Ghattali, N. Golzar, J. Iran Chem. Soc. 8, 411 (2011)

    Article  CAS  Google Scholar 

  26. H. Zang, Q. Su, Y. Mo, B. Cheng, Ultrason. Sonochem. 18, 68 (2011)

    Article  CAS  Google Scholar 

  27. K.R. Phatangare, V.S. Padalkar, V.D. Gupta, V.S. Patil, P.G. Umape, N. Sekar, Synth. Commun. 42, 1349 (2012)

    Article  CAS  Google Scholar 

  28. M.A. Gouda, A.A. Abu-Hashem, Green Lett. Rev. 5, 203 (2012)

    Article  CAS  Google Scholar 

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

    Article  CAS  Google Scholar 

  30. K. Niknam, M. Sadeghi Habibabad, A. Deris, N. Aeinjamshid, Monatsh Chem. 144, 987 (2013)

    Article  CAS  Google Scholar 

  31. K. Niknam, D. Saberi, M. Sadegheyan, A. Deris, Tetrahedron Lett. 51, 692 (2010)

    Article  CAS  Google Scholar 

  32. E. Soleimani, S. Ghorbani, M. Taran, A. Sarvary, CR Chimie 15, 955 (2012)

    Article  CAS  Google Scholar 

  33. D. Singh, D. Singh, J. Chem. Eng. Data 29, 355 (1984)

    Article  CAS  Google Scholar 

  34. A. Hasaninejad, A. Zare, M. Shekouhy, N. Golzar, Org. Prep. Proced. Int. 43, 131 (2011)

    Article  CAS  Google Scholar 

  35. N.P. Tale, G.B. Tiwari, N.N. Karade, Chin. Chem. Lett. 22, 1415 (2011)

    Article  CAS  Google Scholar 

  36. M.N. Elinson, A.S. Dorofeev, R.F. Nasybullin, G.I. Nikishin, Synthesis 12, 1933 (2008)

    Article  Google Scholar 

  37. T. Okuhara, N. Mizuno, M. Misono, Adv. Catal. 41, 113 (1996)

    CAS  Google Scholar 

  38. A. Davoodnia, M. Bakavoli, Gh Barakouhi, N. Tavakoli-Hoseini, Chin. Chem. Lett. 18, 1483 (2007)

    Article  CAS  Google Scholar 

  39. I.V. Kozhevnikov, Chem. Rev. 98, 171 (1998)

    Article  CAS  Google Scholar 

  40. I.V. Kozhevnikov, Catal. Rev. Sci. Eng. 37, 311 (1995)

    Article  CAS  Google Scholar 

  41. A. Emrani, A. Davoodnia, N. Tavakoli-Hoseini, Bull. Korean Chem. Soc. 32, 2385 (2011)

    Article  CAS  Google Scholar 

  42. A. Khojastehnezhad, A. Davoodnia, M. Bakavoli, N. Tavakoli-Hoseini, M. Zeinali-Dastmalbaf, Chin. J. Chem. 29, 297 (2011)

    Article  CAS  Google Scholar 

  43. A. Davoodnia, A. Zare-Bidaki, H. Behmadi. Chin. J. Catal. 33, 1797 (2012)

    Article  CAS  Google Scholar 

  44. F. Taghavi-Khorasani, A. Davoodnia, Res. Chem. Intermed. (2013). doi:10.1007/s11164-013-1356-0

    Google Scholar 

  45. M.M. Mojtahedi, M.R. Jalali, M.S. Abaee, M. Bolourtchian, Heterocycl. Commun. 12, 225 (2006)

    CAS  Google Scholar 

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Acknowledgments

The authors express their gratitude to the Islamic Azad University, Mashhad Branch for its financial support.

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Authors and Affiliations

  1. Department of Chemistry, Mashhad Branch, Islamic Azad University, Mashhad, Iran

    Asieh Vafaee, Abolghasem Davoodnia & Mehdi Pordel

Authors
  1. Asieh Vafaee
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  2. Abolghasem Davoodnia
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  3. Mehdi Pordel
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Correspondence to Abolghasem Davoodnia.

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Vafaee, A., Davoodnia, A. & Pordel, M. A rapid, efficient, and high-yielding synthesis of 4,4′-(arylmethylene)bis(3-methyl-1H-pyrazol-5-ol) derivatives catalyzed by 12-tungstophosphoric acid (H3PW12O40). Res Chem Intermed 41, 8343–8354 (2015). https://doi.org/10.1007/s11164-014-1896-y

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