Skip to main content
SpringerLink
Log in

One-drop organocatalyzed multicomponent synthesis of pyrazolo[1,2-b]phthalazine-diones and pyrazolophthalazinyl quinolines

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

Abstract

The catalytic potential of organocatalyst N-methylimidazole is explored in the multicomponent reactions of aromatic aldehydes, malononitrile and 2,3-dihydro-phthalazine-1,4-dione/5-amino-2,3-dihydro-phthalazine-1,4-dione for the synthesis of pyrazolo[1,2-b]phthalazine-diones in ethanol under reflux conditions. The protocol has been successfully extended for the synthesis of pyrazolophthalazinyl quinolines using one-pot three-component reactions of 2-chloro-3-formylquinoline, malononitrile/ethyl cyanoacetate and 2,3-dihydro-phthalazine-1,4-dione/5-nitro-2,3-dihydro-phthalazine-1,4-dione. The reported method describes a straightforward and highly efficient protocol with remarkable advantages, including wide substrate scope, ready availability, lower cost of catalyst, operational simplicity and good to high isolated yields along with in-flask catalyst recycling.

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
Fig. 2

Similar content being viewed by others

References

  1. B. List, Chem. Rev. 107, 5413 (2007)

    Article  CAS  Google Scholar 

  2. A. Dondoni, A. Massi, Angew. Chem. Int. Ed. 47, 4638 (2008)

    Article  CAS  Google Scholar 

  3. G. Greco, Synlett 17, 2595 (2011)

    Article  Google Scholar 

  4. A. Pande, K. Ganesan, A.K. Jain, P.K. Gupta, R.C. Malhotra, Org. Process Res. Dev. 9, 133 (2005)

    Article  CAS  Google Scholar 

  5. H. Hagiwara, H. Inoguchi, M. Fukushima, T. Hoshi, T. Suzuki, Tetrahedron Lett. 47, 5371 (2006)

    Article  CAS  Google Scholar 

  6. X.Z. Lian, Y. Huang, Y.Q. Li, W.J. Zheng, Monatsh. Chem. 139, 129 (2008)

    Article  CAS  Google Scholar 

  7. A. Domling, Chem. Rev. 106, 17 (2006)

    Article  PubMed  Google Scholar 

  8. H.S. Oboudatian, J. Safaei-Ghomi, Sci. Rep. 12, 1 (2022)

    Article  Google Scholar 

  9. H.S. Oboudatian, J. Safaei-Ghomi, Res. Chem. Intermed. 48, 2069 (2022)

    Article  CAS  Google Scholar 

  10. N.K. Terrett, A.S. Bell, D. Brown, P. Ellis, Bioorg. Med. Chem. Lett. 6, 1819 (1996)

    Article  Google Scholar 

  11. 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 (2000)

    Article  CAS  PubMed  Google Scholar 

  12. D. O’Hagan, J. Fluor. Chem. 131, 1071 (2010)

  13. F. Al'-Assar, K.N. Zelenin, E.E. Lesiovskaya, I.P. Bezhan, B.A. Chakchir, Pharm. Chem. J. 36, 598 (2002)

    Article  CAS  Google Scholar 

  14. R.P. Jain, J.C. Vederas, Bioorg. Med. Chem. Lett. 14, 3655 (2004)

    Article  CAS  PubMed  Google Scholar 

  15. S. Grasso, G. De Sarro, A. De Sarro, N. Micale, M. Zappala, G. Puja, M. Baraldi, C. De Micheli, J. Med. Chem. 43, 2851 (2000)

    Article  CAS  PubMed  Google Scholar 

  16. N. Watanabe, Y. Kabasawa, Y. Takase, M. Matsukura, K. Miyazaki, H. Ishihara, K. Kodama, H. Adachi, J. Med. Chem. 41, 3367 (1998)

  17. A.M. Khalil, M.A. Berghot, M.A. Gouda, Eur J Med Chem. 44, 4448 (2009)

    Article  CAS  PubMed  Google Scholar 

  18. J.S. Kim, H.-J. Lee, M.-E. Suh, H.-Y. Park Choo, S.K. Lee, H.J. Park, C. Kim, S.W. Park, C.-O. Lee, Bioorg. Med. Chem. 12, 3683 (2004)

  19. R. Ghahremanzadeh, G.I. Shakibaei, A. Bazgir, Synlett 8, 1129 (2008)

    Google Scholar 

  20. M.R. Nabid, S.J.T. Rezaei, R. Ghahremanzadeh, A. Bazgir, Ultrason. Sonochem. 17, 159 (2010)

    Article  CAS  PubMed  Google Scholar 

  21. D.S. Raghuvanshi, K.N. Singh, Tetrahedron Lett. 52, 5702 (2011)

    Article  CAS  Google Scholar 

  22. H.R. Shaterian, M. Mohammadnia, J. Mol. Liq. 173, 55 (2012)

  23. S.R. Shafe-Mehrabadi, B. Sadeghi, A. Hassanabadi, Polycycl. Aromat. Compd. 42, 574 (2022)

  24. A.G. Mulik, D.R. Chandam, D.R. Patil, P.P. Patil, G.N. Mulik, S.T. Salunkhe, M.B. Deshmukh, Res. Chem. Intermed. 41, 10085 (2015)

    Article  CAS  Google Scholar 

  25. A. Chaskar, Current Catalysis. 3, 266 (2014)

    Article  CAS  Google Scholar 

  26. N.M. Shah, M.P. Patel, R.G. Patel, J. Heterocycl. Chem. 49, 1310 (2012)

  27. Y.A. Tayade, D.S. Dalal, Catal. Lett. 147, 1411 (2017)

    Article  Google Scholar 

  28. M. Barge, S. Kamble, A. Kumbhar, G. Rashinkar, R. Salunkhe, Monatsh. Chem. 144, 1213 (2013)

    Article  CAS  Google Scholar 

  29. A. Patil, M. Barge, G. Rashinkar, R. Salunkhe, Mol. Divers. 19, 435 (2015)

    Article  CAS  PubMed  Google Scholar 

  30. T. Lohar, A. Kumbhar, M. Barge, R. Salunkhe, J. Mol. Liq. 224, 1102 (2016)

  31. G.V. Reddy, S.R. Kanth, D. Maitraie, B. Narsaiah, P.S. Rao, K.H. Kishore, U.S.N. Murthy, B. Ravi, B. Ashok Kumar, T. Parthasarathy, Eur. J. Med. Chem. 44, 1570 (2009)

  32. C.M. Melendez Gomez, V.V. Kouznetsov, M.A. Sortino, S.L. Alvarez, S.A. Zacchino, Bioorg. Med. Chem. 16, 7908 (2008)

    Article  CAS  PubMed  Google Scholar 

  33. G. Li-Ping, J. Qing-Hao, T. Guan-Rong, C. Kyu-Yun, Q. Zhe-Shan, J. Pharma. Pharmaceut. Sci. 10, 254 (2007)

    Google Scholar 

  34. T.C. Ko, M.J. Hour, J.C. Lien, C.M. Teng, K.H. Lee, S.C. Kuo, L.J. Huang, Bioorg. Med. Chem. Lett. 11, 279 (2001)

    Article  CAS  PubMed  Google Scholar 

Download references

Acknowledgements

The authors are thankful to the Department of Chemistry, Shivaji University, Kolhapur, and CSIR-National Chemical Laboratory, Pune, for providing spectral data.

Author information

Authors and Affiliations

  1. Rayat Shikshan Sanstha’s Yashavantrao Chavan Institute of Science (Autonomous), Satara, MS, 415004, India

    Madhuri Barge

  2. Department of Chemistry, Shivaji University, Kolhapur, MS, 416004, India

    Gajanan Rashinkar

  3. Bharati Vidyapeeth’s Dr. Patangrao Kadam Mahavidyalaya, Sangli, MS, 416416, India

    Dhanaji Kanase & Trushant Lohar

  4. Bharati Vidyapeeth (Deemed to be University) Yashwantrao Mohite College of Arts, Science and Commerce, Pune, MS, 411038, India

    Suhas Mohite

Authors
  1. Madhuri Barge
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Gajanan Rashinkar
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Dhanaji Kanase
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. Suhas Mohite
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. Trushant Lohar
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Trushant Lohar.

Ethics declarations

Conflict of interest

The authors declare no conflict.

Additional information

Publisher's Note

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

Rights and permissions

Springer Nature or its licensor (e.g. a society or other partner) holds exclusive rights to this article under a publishing agreement with the author(s) or other rightsholder(s); author self-archiving of the accepted manuscript version of this article is solely governed by the terms of such publishing agreement and applicable law.

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Barge, M., Rashinkar, G., Kanase, D. et al. One-drop organocatalyzed multicomponent synthesis of pyrazolo[1,2-b]phthalazine-diones and pyrazolophthalazinyl quinolines. Res Chem Intermed 48, 5045–5058 (2022). https://doi.org/10.1007/s11164-022-04848-w

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s11164-022-04848-w

Keywords

Search

Navigation