Skip to main content
SpringerLink
Log in

One-pot green synthesis of novel 5,10-dihydro-1H-pyrazolo[1,2-b]phthalazine derivatives with eco-friendly biodegradable eggshell powder as efficacious catalyst

  • Published:
Research on Chemical Intermediates Aims and scope Submit manuscript

Abstract

An eco-friendly and efficient green protocol is developed for the synthesis of sixteen pyrazolo-phthalazine derivatives (5a–p) by using inexpensive biodegradable eggshell powder (ESP) as a heterogeneous catalyst. The four-component one-pot condensation reaction proceeded through Knoevenagel–Michael reaction of different chosen active methylene compounds, phthalic anhydride, and hydrazine hydride with various substituted aromatic aldehydes in the water at 60 °C, and furnished the high yields of products (93–98%) in rapid reaction time of 28 to 45 min. The material was characterized by different analytical techniques (SEM, TEM, XRD, BET, and FT-IR), and was composed of the high percentage of calcium oxides and carbonates, and less percentage of Na and Mg elements (based on EDX analysis). The ESP material displayed recyclability (4 times) without any notable loss of catalytic efficacy. Besides, this procedure offers 98% of the atom economy and 100% of carbon efficiency together with significant fiscal and enviro-friendly benefits.

Graphic 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

Scheme 1
Fig. 1
Fig. 2
Fig. 3
Fig. 4
Fig. 5
Scheme 2

Similar content being viewed by others

References

  1. S.S. Chavan, M.S. Degani, Green Chem. 14, 296 (2012)

    Article  CAS  Google Scholar 

  2. A. Kumar, M.K. Gupta, M. Kumar, Green Chem. 14, 290 (2012)

    Article  CAS  Google Scholar 

  3. Q. Zhang, H. Su, J. Luo, Y.Y. Wei, Green Chem. 14, 201 (2012)

    Article  CAS  Google Scholar 

  4. E. Kolvari, S. Zolfagharinia, RSC Adv. 6, 93963 (2016)

    Article  CAS  Google Scholar 

  5. H. Faridi, A. Arabhosseini, Res. Agric. Eng. 64, 104 (2018)

    Article  CAS  Google Scholar 

  6. A.K. Jagadeesan, J.A. Duvuru, J.S. Anuradha, S.K. Ponnusamy, V.A. Kabali, N. Gopakumaran, K.R.N. Selvaraj, K. Thangavelu, S. Sunny, P.P. Somasundaram, Y. Devarajan, J. Clean. Prod. 237, 117691 (2019)

    Article  CAS  Google Scholar 

  7. J.A. Kumar, D.J. Amarnath, P.S. Kumar, C.S. Kaushik, M.E. Varghese, A. Saravanan, Desalin. Water Treat. 106, 238 (2018)

    Article  CAS  Google Scholar 

  8. Y. Guo, Y. Sun, D.P. Yang, J. Dai, Z. Liu, Y. Chen, J. Huang, Q. Li, A.C.S. Appl, Mater. Interfaces 12, 2469 (2020)

    Article  CAS  Google Scholar 

  9. Q. Ding, Z. Kang, L. Cao, M. Lin, H. Lin, D.P. Yang, Appl. Surf. Sci. 510, 145526 (2020)

    Article  CAS  Google Scholar 

  10. X. Zhang, J. Huang, Z. Kang, D.P. Yang, R. Lupue, Mol. Catal. 484, 110786 (2020)

    Article  CAS  Google Scholar 

  11. X. Zhang, M. Liu, Z. Kang, B. Wang, B. Wang, F. Jiang, X. Wang, D.P. Yang, R. Luque, Chem. Eng. J. 388, 124304 (2020)

    Article  CAS  Google Scholar 

  12. A. Laca, A. Laca, M. Diaz, J. Environ. Manag. 197, 351 (2017)

    Article  CAS  Google Scholar 

  13. M. Balaz, Acta Biomater. 10, 3827 (2014)

    Article  CAS  PubMed  Google Scholar 

  14. M. Nasrollahzadeh, S.M. Sajadi, A. Hatamifard, Appl. Catal. B Environ. 191, 209 (2016)

    Article  CAS  Google Scholar 

  15. F.D. Kopinke, A. Georgi, K.U. Goss, Water Res. 129, 520 (2018)

    Article  CAS  PubMed  Google Scholar 

  16. H.N. Tran, S.J. You, A.H. Bandegharaei, H.P. Chao, Water Res. 120, 88 (2017)

    Article  CAS  PubMed  Google Scholar 

  17. S.B. Chavan, R.R. Kumbhar, D. Madhu, B. Singh, Y.C. Sharma, RSC Adv. 5, 63596 (2015)

    Article  CAS  Google Scholar 

  18. S. Niju, K.M. Meera, S. Begum, N. Anantharaman, J. Saudi Chem. Soc. 18, 702 (2014)

    Article  CAS  Google Scholar 

  19. A. Montilla, M.D. del Castillo, M.L. Sanz, A. Olano, Food Chem. 90, 883 (2005)

    Article  CAS  Google Scholar 

  20. S.M. Fan, X.Z. Yuan, L. Zhao, L.H. Xu, T.J. Kang, H.T. Kim, Fuel 165, 397 (2016)

    Article  CAS  Google Scholar 

  21. J. Rovensky, M. Stancikova, P. Masaryk, K. Svik, R. Istok, Int. J. Clin. Pharmacol. Res. 23, 83 (2003)

    CAS  PubMed  Google Scholar 

  22. Y. Gao, C. Xu, Catal. Today 190, 107 (2012)

    Article  CAS  Google Scholar 

  23. S. Patil, S. Jadhav, M.B. Deshmukh, J. Chem. Sci. 125, 851 (2013)

    Article  CAS  Google Scholar 

  24. E. Mosaddegh, A. Hassankhani, Chinese. J. Catal. 35, 351 (2014)

    CAS  Google Scholar 

  25. E. Mosaddegh, Ultrason. Sonochem. 20, 1436 (2013)

    Article  CAS  PubMed  Google Scholar 

  26. E. Mosaddegh, A. Hassankhani, Catal. Commun. 33, 70 (2013)

    Article  CAS  Google Scholar 

  27. A.V. Borhade, B.K. Uphade, A.G. Gadhave, Res. Chem. Intermed. 42, 6301 (2016)

    Article  CAS  Google Scholar 

  28. M. Asif, Curr. Med. Chem. 19, 2984 (2012)

    Article  CAS  PubMed  Google Scholar 

  29. X. Deng-Qi, Z. Xu-Yao, W. Chao-Jie, M. Li-Ying, Z. Nan, H. Peng, S. Kun-Peng, C. Peng-Ju, G. Yi-Fei, Z. Xiao-Song, W. Cai-Feng, J. Cong-Hui, Z. Qiu-Rong, L. Hong-Min, Eur. J. Med. Chem. 85, 235 (2014)

    Article  CAS  Google Scholar 

  30. A.G.A. El-Helby, R.R. Ayyad, H.M. Sakr, A.S. Abdelrahim, K. El-Adl, F.S. Sherbiny, I.H. Eissa, M.M. Khalifa, J. Mol. Struct. 1130, 333 (2017)

    Article  CAS  Google Scholar 

  31. Z. Qiu-Rong, X. Deng-Qi, H. Peng, S. Kun-Peng, C. Peng-Ju, G. Yi-Fei, R. Jing-Li, S. Li-Hong, L. Hong-Min, Bioorg. Med. Chem. Lett. 24, 1236 (2014)

    Article  CAS  Google Scholar 

  32. B. Maleki, S.B.N. Chalaki, S.S. Ashrafi, E.R. Seresht, F. Moeinpour, A. Khojastehnezh, R. Tayebe, Appl. Organomet. Chem. 29, 290 (2015)

    Article  CAS  Google Scholar 

  33. R.G. Vaghei, J. Mahmoodi, Y. Maghbooli, Appl. Organomet. Chem. 31, e3717 (2017)

    Article  CAS  Google Scholar 

  34. P. Arora, J.K. Rajput, Appl. Organomet. Chem. 32, e4001 (2017)

    Google Scholar 

  35. E. Mosaddegh, A. Hassankhani, Catal. Commun. 71, 65 (2015)

    Article  CAS  Google Scholar 

  36. J.S. Ghomi, H.S. Alavi, A. Ziarati, R. Teymuri, M.R. Saberi, Chem. Lett. 25, 401 (2014)

    Google Scholar 

  37. F. Mohamadpour, M.T. Maghsoodlou, R. Heydari, M. Lashkari, Res. Chem. Intermed. 42, 7841 (2016)

    Article  CAS  Google Scholar 

  38. R.G. Vaghei, S. Noori, Z.T. Semiromi, Z. Salimi, RSC Adv. 4, 47925 (2014)

    Article  CAS  Google Scholar 

  39. C.S. Maheswari, C. Shanmugapriya, K. Revathy, A. Lalitha, J. Nanostruct. Chem. 7, 283 (2017)

    Article  CAS  Google Scholar 

  40. S. Patil, A. Mane, S.D. Desai, J. Iran. Chem. Soc. 16, 1665 (2019)

    Article  CAS  Google Scholar 

  41. R. Tayebee, B. Maleki, M. Sabeti, J. Iran. Chem. Soc. 14, 1176 (2017)

    Article  CAS  Google Scholar 

  42. M.V. Reddy, Y.T. Jeong, Tetrahedron Lett. 54, 3546 (2013)

    Article  CAS  Google Scholar 

  43. N. Kerru, S.V.H.S. Bhaskaruni, L. Gummidi, S.N. Maddila, S. Rana, P. Singh, S.B. Jonnalagadda, Appl. Organomet. Chem. 33, e4722 (2019)

    Article  CAS  Google Scholar 

  44. N. Kerru, S.V.H.S. Bhaskaruni, L. Gummidi, S.N. Maddila, P. Singh, S.B. Jonnalagadda, Mol. Divers. (2019)

  45. T. Liu, Y. Zhu, X. Zhang, T. Zhang, T. Zhang, X. Li, Mater. Lett. 64, 2575 (2010)

    Article  CAS  Google Scholar 

  46. A. Antonakos, E. Liarokapis, T. Leventouri, Biomaterials 28, 3043 (2007)

    Article  CAS  PubMed  Google Scholar 

  47. Y. Yanagisawa, S. Kashima, Surf. Sci. 454, 379 (2000)

    Article  Google Scholar 

  48. M.J. Blesa, J.L. Miranda, R. Moliner, Vib. Spectrosc. 33, 31 (2003)

    Article  CAS  Google Scholar 

  49. M.V. Reddy, P.C.R. Kumar, G.C.S. Reddy, C.S. Reddy, C. R. Chimie 17, 1250 (2014)

    Article  CAS  Google Scholar 

Download references

Acknowledgements

The authors are thanks to the University of KwaZulu-Natal, Durban, South Africa, for financial support and research facilities.

Author information

Authors and Affiliations

  1. School of Chemistry and Physics, University of KwaZulu-Natal, Westville Campus, Chiltern Hills, Durban, 4000, South Africa

    Nagaraju Kerru, Lalitha Gummidi, Sandeep V. H. S. Bhaskaruni, Surya Narayana Maddila & Sreekantha B. Jonnalagadda

Authors
  1. Nagaraju Kerru
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Lalitha Gummidi
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Sandeep V. H. S. Bhaskaruni
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. Surya Narayana Maddila
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. Sreekantha B. Jonnalagadda
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Sreekantha B. Jonnalagadda.

Additional information

Publisher's Note

Springer Nature remains neutral with regard to jurisdictional claims in published maps and institutional affiliations.

Electronic supplementary material

Below is the link to the electronic supplementary material.

Supplementary file1 (DOCX 2725 kb)

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Kerru, N., Gummidi, L., Bhaskaruni, S.V.H.S. et al. One-pot green synthesis of novel 5,10-dihydro-1H-pyrazolo[1,2-b]phthalazine derivatives with eco-friendly biodegradable eggshell powder as efficacious catalyst. Res Chem Intermed 46, 3067–3083 (2020). https://doi.org/10.1007/s11164-020-04135-6

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s11164-020-04135-6

Keywords

Search

Navigation