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Pumice-based sulfonic acid: a sustainable and recyclable acidic catalyst for one-pot synthesis of pyrazole anchored 1,4-dihydropyridine derivatives at room temperature

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Abstract

In the present investigation, we have developed an efficient and eco-friendly protocol for the synthesis of pyrazole anchored 1,4-dihydropyridine analogs using pumice-based sulfonic acid (pumice@SO3H) as a recyclable solid acid catalyst under simple stirring at room temperature. The present protocol proceeded smoothly with 1,3-diaryl pyrazole-4-carbaldehydes, ethyl acetoacetate, and NH4OAc in ethanol as a solvent with excellent yield. The pumice-based sulfonic acid catalyst is easily prepared from naturally occurring pumice by simple agitation with chlorosulfonic acid. The key features of this catalyst are its heterogeneous nature, high porosity, non-corrosive and non-toxic nature, recyclability, stable and highly efficient at room temperature. The application of this catalyst makes the protocol more environmentally benign.

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References

  1. A. Maleki, S. Gharibi, K. Valadi, R. Taheri-Ledari, J. Phys. Chem. Solids. 142, 109443 (2020)

    Article  CAS  Google Scholar 

  2. A. Tambe, A. Gadhave, A. Pathare, G. Shirole, Sustain. Chem. Pharm. 22, 100485 (2021)

    Article  Google Scholar 

  3. K. Valadi, S. Gharibi, R.T. Ledari, A. Maleki, Solid State Sci. 101, 106141 (2020)

    Article  CAS  Google Scholar 

  4. A. Alver, M. Karaarslan, A. Kilic, Environ. Technol. 37, 2040 (2016)

    Article  CAS  PubMed  Google Scholar 

  5. G.S. Kumar, Y. Poornachandra, S.K. Gunda, K.R. Reddy, J. Mohmed, K. Shaik, C.G. Kumar, B. Narsaiah, Bioorg. Med. Chem. Lett. 28, 2328 (2018)

    Article  Google Scholar 

  6. E.R. Kotb, H.S. Abbas, E.M. Flefel, H.H. Sayed, N.A.M. Abdelwahed, J. Heterocycl. Chem. 52, 1531 (2015)

    Article  CAS  Google Scholar 

  7. P. Swiatek, M. Strzelecka, R. Urniaz, K. Gebczak, T. Gebarowski, K. Gasiorowski, W. Malinka, Bioorg. Med. Chem. 25, 316 (2017)

    Article  CAS  PubMed  Google Scholar 

  8. D. Anand, P.K. Yadav, O.P. Patel, N. Parmar, R.K. Maurya, P. Vishwakarma, K.S. Raju, I. Taneja, M. Wahajuddin, S. Kar, P.P. Yadav, J. Med. Chem. 60, 1041 (2017)

    Article  CAS  PubMed  Google Scholar 

  9. N.H. Gokhale, S.B. Padhye, D.C. Billington, D.L. Rathbone, S.L. Croft, H.D. Kendrick, C.E. Anson, A.K. Powell, Inorg. Chim. Acta. 49, 23 (2003)

    Article  Google Scholar 

  10. E.H. El-Sayed, A.A. Fadda, J. Heterocycl. Chem. 55, 2251 (2018)

    Article  CAS  Google Scholar 

  11. E. Baydar, M.G. Gunduz, V.S. Krishna, R. Simsek, D. Sriram, S.O. Yıldırım, R.J. Butcher, C. Safak, Res. Chem. Intermed. 43, 7471 (2017)

    Article  CAS  Google Scholar 

  12. R. Ghorbani-Vaghei, S.M. Malaekehpoor, P. Hasanein, R. Karamyan, M. Asadbegy, Res. Chem. Intermed. 42, 4715 (2016)

    Article  CAS  Google Scholar 

  13. Q. Tang, Y. Duan, L. Wang, M. Wang, Y. Ouyang, C. Wang, H. Mei, S. Tang, Y. Xiong, P. Zheng, P. Gong, W. Zhu, Eur. J. Med. Chem. 143, 266 (2018)

    Article  CAS  PubMed  Google Scholar 

  14. M.A. Abdelrahman, I. Salama, M.S. Gomaa, M.M. Elaasser, M.M. Abdel-Aziz, D.H. Soliman, Eur. J. Med. Chem. 138, 698 (2017)

    Article  CAS  PubMed  Google Scholar 

  15. H.A.S. Abbas, W.A. El Sayed, N.M. Fathy, Eur. J. Med. Chem. 45, 973 (2010)

    Article  CAS  PubMed  Google Scholar 

  16. N.N. El-Sayed, M.A. Abdelaziz, W.W. Wardakhan, R.M. Mohareb, Steroids 107, 98 (2016)

    Article  CAS  PubMed  Google Scholar 

  17. T. Li, J. Zhang, J. Pan, Z. Wu, D. Hu, B. Song, Eur. J. Med. Chem. 125, 657 (2017)

    Article  CAS  PubMed  Google Scholar 

  18. A.K. Kumari, V.H. Reddy, G.M. Reddy, Y.V.R. Reddy, S. Leelavathi, J. Heterocycl. Chem 56, 1661 (2019)

    Article  Google Scholar 

  19. G.B. Dharma Rao, J. Heterocycl. Chem. 52, 2556 (2018)

    Article  Google Scholar 

  20. M.R. Khumalo, S.N. Maddila, S. Maddila, S.B. Jonnalagadda, Chemistry Select 4, 12503 (2019)

    CAS  Google Scholar 

  21. M. Abaszadeh, M. Seifi, A. Asadipour, Res. Chem. Intermed. 41, 5229 (2015)

    Article  CAS  Google Scholar 

  22. S.J. Ji, Z.Q. Jiang, J. Lu, T.P. Loa, Synlett 5, 831 (2004)

    Article  Google Scholar 

  23. N. Ahadi, A. Mobinikhaledi, M.A. Bodaghifard, Appl. Organomet. Chem. 34, e5822 (2020)

    Article  CAS  Google Scholar 

  24. H. Alinezhad, S.M. Tavakkoli, Res. Chem. Intermed. 41, 5931 (2015)

    Article  CAS  Google Scholar 

  25. R.A. Mekheimer, A.A. Hameed, K.U. Sadek, Green Chem. 10, 592 (2008)

    Article  CAS  Google Scholar 

  26. J.F. Zhou, Y.Z. Song, J.S. Lv, G.X. Gong, S. Tu, Synth. Commun. 39, 8 (2009)

    Google Scholar 

  27. R. Farsi, M.K. Mohammadi, S.J. Saghanezhad, Res. Chem. Intermed. 47, 1161 (2020)

    Article  Google Scholar 

  28. S.S. Mansoor, K. Aswin, K. Logaiya, P.N. Sudhan, S. Malik, Res. Chem. Intermed. 40, 2 (2014)

    Google Scholar 

  29. S. Zhaleh, N. Hazeri, M.R. Faghihi, M.T. Maghsoodlou, Res. Chem. Intermed. 42, 8089 (2016)

    Google Scholar 

  30. S.N. Maddila, S. Maddila, K.K. Gangu, W.E. van Zyl, S.B. Jonnalagadda, J. Fluor. Chem. 195, 79 (2017)

    Article  CAS  Google Scholar 

  31. T. Akbarpoor, A. Khazaei, J.Y. Seyf, N. Sarmasti, M.M. Gilan, Res. Chem. Intermed. 46, 1539 (2020)

    Article  CAS  Google Scholar 

  32. Z. Shahamat, F. Nemati, A. Elhampour, Res. Chem. Intermed. 44, 6649 (2018)

    Article  CAS  Google Scholar 

  33. A. Shaabani, S. Shaabani, M. Seyyedhamzeh, M.H. Sangachin, F. Hajishaabanha, Res. Chem. Intermed. 42, 7247 (2016)

    Article  CAS  Google Scholar 

  34. S.K. Singh, K.N. Singh, J. Heterocycl. Chem. 47, 194 (2010)

    CAS  Google Scholar 

  35. A.G. Sathicq, G.P. Romanelli, A. Ponzinibbio, G.T. Baronetti, H.J. Thomas, Lett. Org. Chem. 7, 511 (2010)

    Article  CAS  Google Scholar 

  36. A. Kumar, R.A. Maurya, Tetrahedron 63, 1946 (2007)

    Article  CAS  Google Scholar 

  37. A. Maleki, M. Kamalzare, M. Aghaei, J. Nanostruct. Chem. 5, 95 (2015)

    Article  CAS  Google Scholar 

  38. M.G. Dehbalaei, N. Foroughifar, A. Khajeh-Amiri, H. Pasdar, J. Chin. Chem. Soc. 65, 1356 (2018)

    Article  Google Scholar 

  39. C.G. Evans, J.E. Gestwicki, Org. Lett. 11, 2957 (2009)

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  40. A. Khojastehnezhad, F. Moeinpour, A. Davoodnia, Chin. Chem. Lett. 22, 807 (2011)

    Article  CAS  Google Scholar 

  41. A. Kumar, R.A. Maurya, Synlett 6, 883 (2008)

    Article  Google Scholar 

  42. S. Ko, C.F. Yao, Tetrahedron 62, 7293 (2006)

    Article  CAS  Google Scholar 

  43. S. Wu, J. Wang, W. Zhang, X. Ren, Catal. Lett. 125, 3 (2008)

    Article  Google Scholar 

  44. S.S. Mansoor, K. Aswin, K. Logaiya, P.N. Sudhan, S. Malik, Res. Chem. Intermed. 40, 357 (2012)

    Article  Google Scholar 

  45. P. Suman, H.C. Lokman, P. Tasneem, Synth. Commun. 43, 986 (2013)

    Article  Google Scholar 

  46. G.D. Shirole, R.A. Mokal, S.N. Shelke, Lett. Org. Chem. 14, 548 (2017)

    Article  CAS  Google Scholar 

  47. R. Murugan, K. Ramamurthy, S. Sundarrajan, S. Ramakrishna, Tetrahedron 68, 7196 (2012)

    Article  CAS  Google Scholar 

  48. P. Kumara, K. Hussain, A. Kumar, Curr. Chem. Lett. 3, 75 (2014)

    Article  Google Scholar 

  49. K.A. More, N.V. Gandhare, P.S. Ali, N.B. Pathan, K.M. Al-Mousa, Curr. Res. Green Sustain. Chem. 4, 100108 (2021)

    Article  Google Scholar 

  50. J. Li, J. Qiu, H. Li, G. Zhang, Chin. J. Chem. 29, 511 (2011)

    Article  CAS  Google Scholar 

  51. G.D. Shirole, A.S. Tambe, S.N. Shelke, Indian J. Chem. Sec B. 59B, 459 (2020)

    CAS  Google Scholar 

  52. G.D. Shirole, V.A. Kadnor, A.S. Tambe, S.N. Shelke, Res. Chem. Intermed. 43, 1089 (2017)

    Article  CAS  Google Scholar 

  53. G.D. Shirole, S. Bhalekar, S.N. Shelke, Indian J. Chem. Sec B. 57B, 1430 (2018)

    CAS  Google Scholar 

  54. V. Kadnor, A. Tambe, G. Shirole, Heterocycl. Lett. 10, 407 (2020)

    CAS  Google Scholar 

  55. G. Shirole, V. Kadnor, S. Gaikwad, N. Kshirsagar, G. Mhaske, S. Shelke, Res. Chem. Intermed. 42, 4785 (2016)

    Article  CAS  Google Scholar 

  56. V.A. Chornous, M.K. Bratenko, M.V. Vovk, Chem. Heterocycl. Compd. 42, 1242 (2006)

    Article  CAS  Google Scholar 

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Acknowledgements

The authors are grateful to the Principal of ASC College, Rahata for providing the necessary facilities and SAIF, University of Punjab, Chandigarh for providing the spectral characterization.

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Correspondence to Gopinath Shirole.

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Tambe, A., Sadaphal, G., Dhawale, R. et al. Pumice-based sulfonic acid: a sustainable and recyclable acidic catalyst for one-pot synthesis of pyrazole anchored 1,4-dihydropyridine derivatives at room temperature. Res Chem Intermed 48, 1273–1286 (2022). https://doi.org/10.1007/s11164-021-04649-7

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