Skip to main content
SpringerLink
Log in

Aspirin: an efficient catalyst for synthesis of bis (pyrazol-5-ols), dihydropyrano[2,3-c]pyrazoles and spiropyranopyrazoles in an environmentally benign manner

  • Original Paper
  • Published:
Journal of the Iranian Chemical Society Aims and scope Submit manuscript

Abstract

This article aimed to present two facile and environmental friendly routes for the rapid assembly of biologically active compounds including pyrazol core using aspirin as a novel and green catalyst. The synthesis of bis(pyrazol-5-ol) derivatives was developed via one-pot, pseudo-five-component condensation, and the target dihydropyrano[2,3-c]pyrazoles and spiropyranopyrazoles were prepared by one-pot, four-component reaction. These reactions can be performed in tandem from readily available starting materials. The main merits of the present methods are operational simplicity, no need for column chromatography, inexpensive materials, avoidance of harmless and corrosive acid catalysts, short reaction times, good yields of the products, and utilization of aspirin as a non-toxic, cheap, commercially available, and efficient catalyst.

Graphical abstract

This is a preview of subscription content, log in via an institution to check access.

Access this article

Log in via an institution

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Institutional subscriptions

Fig. 1
Scheme 1
Scheme 2

Similar content being viewed by others

References

  1. S. Karamthulla, S. Pal, M.N. Khan, L.H. Choudhury, RSC Adv. 4, 37889–37899 (2014)

    Article  CAS  Google Scholar 

  2. P.T. Anastas, T.C. Williamson (eds.), Green Chemistry: Frontiers in Benign Chemical Syntheses and Processes (Oxford University Press, Oxford, 1998)

    Google Scholar 

  3. G.M. Ziarani, S. Faramarzi, N. Lashgari, A. Badiei, J. Iran. Chem. Soc. 11, 701–709 (2014)

    Article  Google Scholar 

  4. P.T. Anastas, M.M. Kirchhoff, Acc. Chem. Res. 35, 686–694 (2002)

    Article  CAS  Google Scholar 

  5. E. Ruijter, R. Scheffelaar, R.V.A. Orru, Angew. Chem. Int. Ed. 50, 6234–6246 (2011)

    Article  CAS  Google Scholar 

  6. J.L. Tucker, Org. Process Res. Dev. 10, 315–319 (2006)

    Article  CAS  Google Scholar 

  7. O.A. Attanasi, D. Spinelli, Soc. Chim. Italiana, Roma. 4, 105–137 (2000)

    Google Scholar 

  8. M.M.F. Ismail, Y.A. Ammar, H.S.A. EI-Zahaby, S.I. Eisa, S.E. Barakat, Arch. Pharm. Chem. Life Sci. 340, 476–479 (2007)

    Article  CAS  Google Scholar 

  9. S.P. Prajapati, D.P. Patel, P.S. Patel, J. Chem. Pharm. Res. 4, 2652–2655 (2012)

    CAS  Google Scholar 

  10. Y. Liu, G. He, C. Kai, Y. Li, H. Zhu, J. Heterocycl. Chem. 19, 1370–1375 (2012)

    Article  Google Scholar 

  11. G. Mariappan, B.P. Saha, L. Sutharson, A. Singh, S. Garg, L. Pandey, D. Kumar, Saudi Pharm. J. 19, 115–122 (2011)

    Article  CAS  Google Scholar 

  12. C.E. Rosiere, M.I. Grossman, Science 131, 651 (1951)

    Article  Google Scholar 

  13. M.G. LaPorte, Z. Wang, R. Colombo, A. Garzan, V.A. Peshkov, M. Liang, P.A. Johnston, M.E. Schurdak, M. Sen, D.P. Camarco, Y. Hua, Bioorg. Med. Chem. Lett. 26, 3581–3588 (2016)

    Article  CAS  Google Scholar 

  14. J.L. Wang, D. Liu, Z.J. Zheng, S. Shan, X. Han, S.M. Srinivasula, C.M. Croce, E.S., Z. Huang. Proc. Natl. Acad. Sci. 97, 7124–7129 (2009)

    Article  Google Scholar 

  15. B.P. Bandgar, H.V. Chavan, L.K. Adsul, V.N. Thakare, S.N. Shringare, R. Shaikh, R.N. Gacche, Bioorg. Med. Chem. Lett. 23, 912–916 (2013)

    Article  CAS  Google Scholar 

  16. K.M. Kasiotis, E.N. Tzanetou, S.A. Haroutounian, Front. Chem. 2, 1–7 (2014)

    Article  CAS  Google Scholar 

  17. M.J. Genin, C. Biles, B.J. Keiser, S.M. Poppe, S.M. Swaney, W.G. Tarpley, Y. Yagi, D.L. Romero, J. Med. Chem. 43, 1034–1040 (2000)

    Article  CAS  Google Scholar 

  18. F. Abrigach, R. Touzani, Med. Chem. (Los Angeles) 6, 292–298 (2016)

    Article  Google Scholar 

  19. K. Sujatha, G. Shanthi, N.P. Selvam, S. Manoharan, P.T. Perumal, M. Rajendran, Bioorg. Med. Chem. Lett. 19, 4501–4503 (2009)

    Article  CAS  Google Scholar 

  20. H. Kashtoh, M.T. Muhammad, J.J. Khan, S. Rasheed, A. Khan, S. Perveen, K. Javaid, K.M. Khan, M.I. Choudhary, Bioorg. Chem. 65, 61–72 (2016)

    Article  CAS  Google Scholar 

  21. A.V. Stachulski, N.G. Berry, A.C.L. Low, S.L. Moores, E. Row, D.C. Warhurst, I.S. Adagu, J.F. Rossignol, J. Med. Chem. 49, 1450–1454 (2006)

    Article  CAS  Google Scholar 

  22. E. Soleimani, S. Ghorbani, M. Taran, A. Sarvary, C. R. Chim. 15, 955–961 (2012)

    Article  CAS  Google Scholar 

  23. J. Safaei-Ghomi, B. Khojastehbakht-Koopaei, H. Shahbazi-Alavi, RSC Adv. 4, 46106–46113 (2014)

    Article  CAS  Google Scholar 

  24. W. Wang, S.X. Wang, X.Y. Qin, J.T. Li, Synth. Commun. 35, 1263–1269 (2005)

    Article  CAS  Google Scholar 

  25. N.G. Khaligh, S.B.A. Hamid, S.J. Titinchi, Chin. Chem. Lett. 27, 104–108 (2016)

    Article  CAS  Google Scholar 

  26. M.A. Zolfigol, R. Ayazi-Nasrabadi, S. Baghery, V. Khakyzadeh, S. Azizian, J. Mol. Catal. A-Chem. 418–419, 54–67 (2016)

    Article  Google Scholar 

  27. D. Azarifar, Y. Abbasi, Synth. Commun. 46, 745–758 (2016)

    Article  CAS  Google Scholar 

  28. Y.A. Tayade, S.A. Padvi, Y.B. Wagh, D.S. Dalal, Tetrahedron Lett. 56, 2441–2447 (2015)

    Article  CAS  Google Scholar 

  29. R.H. Vekariya, K.D. Patel, H.D. Patel, Res. Chem. Intermed. 42, 7559–7579 (2016)

    Article  CAS  Google Scholar 

  30. C.F. Zhou, J.J. Li, W.K. Su, Chin. Chem. Lett. 27, 1686–1690 (2016)

    Article  CAS  Google Scholar 

  31. A.K. Imene, F. Amina, L. Oumeima, B. Raouf, B. Boudjemaa, D. Abdelmadjid, Lett. Org. Chem. 13, 85–91 (2016)

    Article  Google Scholar 

  32. H. Mecadon, M.R. Rohman, M. Rajbangshi, B. Myrboh, Tetrahedron Lett. 52, 2523–2525 (2011)

    Article  CAS  Google Scholar 

  33. A. Siddekha, A. Nizam, M.A. Pasha, Spectrochim. Acta A. 81, 431–440 (2011)

    Article  CAS  Google Scholar 

  34. A.R. Hajipour, M. Karimzadeh, H. Tavallaei, J. Iran. Chem. Soc. 12, 987–991 (2015)

    Article  CAS  Google Scholar 

  35. K. Ablajan, W. Liju, Y. Kelimu, F. Jun, Mol. Divers. 17, 693–700 (2013)

    Article  CAS  Google Scholar 

  36. D.W.C. MacMillan, Nature 455, 304–308 (2008)

    Article  CAS  Google Scholar 

  37. C.M. Ulrich, J. Bigler, J.D. Potter, Nat. Rev. Cancer 6, 130–140 (2006)

    Article  CAS  Google Scholar 

  38. C. Cena, M.L. Lolli, L. Lazzarato, E. Guaita, G. Morini, G. Coruzzi, S.P. McElroy, I.L. Megson, R. Fruttero, A. Gasco, J. Med. Chem. 46, 747–754 (2003)

    Article  CAS  Google Scholar 

  39. A. Undas, K.E. Brummel-Ziedins, K.G. Mann, Blood 109, 2285–2592 (2007)

    Article  CAS  Google Scholar 

  40. X. Shi, M. Ding, Z. Dong, F. Chen, J. Ye, S. Wan, S.S. Leonard, V. Castronova, V. Vallyathan, Mol. Cell. Biochem. 199, 93–102 (1999)

    Article  CAS  Google Scholar 

  41. T. Roberts, F. Shokraneh, S. Nur, Cochrane Libr (2016). doi:10.1002/14651858.CD012116

    Google Scholar 

  42. M. Fatahpour, F. Noori Sadeh, N. Hazeri, M.T. Maghsoodlou, M. Lashkari, Res. Appl. Chem. 6, 1569–1572 (2016)

    Google Scholar 

  43. M. Kangani, N. Hazeri, M.T. Mghsoodlou, K. Khandan-Barani, M. Kheyrollahi, F. Nezhadshahrokhabadi, J. Iran. Chem. Soc. 12, 47–50 (2015)

    Article  CAS  Google Scholar 

  44. M. Fatahpour, N. Hazeri, M.T. Maghsoodlou, M. Lashkari, Iran. J. Sci. Technol. Trans. A Sci. (2016). doi:10.1007/s40995-016-0064-1

    Google Scholar 

  45. F. Mohamadpour, M.T. Maghsoodlou, R. Heydari, M. Lashkari, J. Iran. Chem. Soc. 13, 1549–1560 (2016)

    Article  CAS  Google Scholar 

  46. M.T. Maghsoodlou, M. Karima, M. Lashkari, B. Adrom, J. Aboonajmi, J. Iran. Chem. Soc. 14, 329–335 (2017)

    Article  CAS  Google Scholar 

  47. J. Xu-dong, D. Hai-feng, L. Ying-jie, C. Jun-gang, L. Da-peng, W. Mao-cheng, Chem. Res. Chin. Univ. 28, 999–1002 (2012)

    Google Scholar 

  48. M. Babaie, H. Sheibani, Arab. J. Chem. 11, 159–162 (2011)

    Article  Google Scholar 

  49. Y. Zou, H. Wub, Y. Hua, H. Liu, X. Zhao, H. Ji, D. Shi, Ultrason. Sonochem. 18, 708–712 (2011)

    Article  CAS  Google Scholar 

  50. B. Maleki, H. Eshghi, M. Barghamadi, N. Nasiri, A. Khojastehnezhad, S. Sedigh Ashrafi, O. Pourshiani, Res. Chem. Intermed. 42, 3071–3093 (2016)

    Article  CAS  Google Scholar 

  51. D.R. Palleros, Experimental Organic Chemistry (Wiley, Hoboken, 2000), p. 494

    Google Scholar 

  52. Y. Zou, Y. Hu, H. Liu, D. Shi, ACS comb. Sci. 14, 38–43 (2011)

    Article  Google Scholar 

  53. S. Paul, K. Pradhan, S. Ghosh, S.K. De, A.R. Das, Tetrahedron 70, 6088–6099 (2014)

    Article  CAS  Google Scholar 

  54. M.N. Elinson, A.I. Ilovaisky, V.M. Merkulova, P.A. Belyakov, F. Barba, B. Batanero, Tetrahedron 68, 5833–5837 (2012)

    Article  CAS  Google Scholar 

Download references

Acknowledgements

We gratefully appreciate the financial support from the Research Council of University of Sistan and Baluchestan.

Author information

Authors and Affiliations

  1. Department of Chemistry, Faculty of Sciences, University of Sistan and Baluchestan, Zahedan, P.O. Box 98135-674, Iran

    Maryam Fatahpour, Fatemeh Noori Sadeh, Nourallah Hazeri & Malek Taher Maghsoodlou

  2. Faculty of Sciences, Velayat University, Iranshahr, Iran

    Mojtaba Lashkari

Authors
  1. Maryam Fatahpour
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Fatemeh Noori Sadeh
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Nourallah Hazeri
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. Malek Taher Maghsoodlou
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. Mojtaba Lashkari
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Nourallah Hazeri.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Fatahpour, M., Noori Sadeh, F., Hazeri, N. et al. Aspirin: an efficient catalyst for synthesis of bis (pyrazol-5-ols), dihydropyrano[2,3-c]pyrazoles and spiropyranopyrazoles in an environmentally benign manner. J IRAN CHEM SOC 14, 1945–1956 (2017). https://doi.org/10.1007/s13738-017-1133-x

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s13738-017-1133-x

Keywords

Search

Navigation