Skip to main content
SpringerLink
Log in

Solvent-free, sonochemical, one-pot, four-component synthesis of 2H-indazolo[2,1-b]phthalazine-triones and 1H-pyrazolo[1,2-b]phthalazine-diones catalyzed by Fe3O4@SiO2-imid-PMAn magnetic nanoparticles

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

Abstract

A practical and green method for the synthesis of 2H-indazolo[2,1-b]phthalazine-triones and 1H-pyrazolo[1,2-b]phthalazine-diones using Fe3O4@SiO2-imid-PMAn nanoparticles as an eco-friendly magnetic catalyst from the four-component condensation, solvent-free reaction of phthalic anhydride, hydrazinium hydroxide, 1,3-diketones, and aldehydes under thermal or ultrasound irradiation at room temperature is described. This new procedure has notable advantages such as operational simplicity, excellent yields, short reaction time, and absence of any tedious work-up or purification. In addition, thermal stability, easy preparation and separation of the catalyst make it a good heterogeneous system and a useful alternative to other heterogeneous catalysts. Also, the catalyst can be easily recovered by a magnetic field and reused for eight consecutive reaction cycles without significant loss of activity.

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
Fig. 3

Similar content being viewed by others

References

  1. J. Yang, H.Q. Li, M.H. Li, J.J. Peng, Y.L. Gu, Adv. Synth. Catal. 354, 688 (2012)

    CAS  Google Scholar 

  2. S. Safaei, I. Mohammadpoor-Baltork, A.R. Khosropour, M. Moghadam, S. Tangestaninejad, V. Mirkhani, Catal. Sci. Technol. 3, 2717 (2013)

    CAS  Google Scholar 

  3. M.P. Clark, S.K. Laughlin, M.J. Laufersweiler, R.G. Bookland, T.A. Brugel, A. Golebiowski, M.P. Sabat, J.A. Townes, J.C. VanRens, J.F. Djung, M.G. Natchus, B. De, L.C. Hsieh, S.C. Xu, R.L. Walter, M.J. Mekel, S.A. Heitmeyer, K.K. Brown, K. Juergens, Y.O. Taiwo, M.J. Janusz, J. Med. Chem. 47, 2724 (2004)

    CAS  PubMed  Google Scholar 

  4. J.S. Kim, H.K. Rhee, H.J. Park, S.K. Lee, C.O. Lee, H.Y.P. Choo, Bioorg. Med. Chem 16, 4545 (2008)

    CAS  PubMed  Google Scholar 

  5. M. Kidwai, N. Nagi, S. Kohli, Acta Pharm. 47, 53 (1997)

    CAS  Google Scholar 

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

    CAS  PubMed  Google Scholar 

  7. R.W. Carling, K.W. Moore, L.J. Street, D. Wild, C. Isted, P.D. Lesson, S. Thomas, D. Ocooner, R.M. Mckernan, K. Quirk, S.M. Cook, J.R. Atach, K.A. Waftord, S.A. Thompson, G.R. Dawson, P. Ferris, J.L. Castro, J. Med. Chem. 47, 1807 (2004)

    CAS  PubMed  Google Scholar 

  8. Y. Nomoto, H. Obase, H. Takai, M. Teranishi, J. Nakamura, K. Kubo, Chem. Pharm. Bull. 38, 2179 (1990)

    CAS  Google Scholar 

  9. J. Li, Y.F. Zhao, X.Y. Yuan, J.X. Xu, P. Gong, Molecules 11, 574 (2006)

    CAS  PubMed  PubMed Central  Google Scholar 

  10. S. Grasso, G. Desarro, N. Micale, M. Zappala, G. Puia, M. Baraldi, C. Demicheli, J. Med. Chem. 43, 2851 (2000)

    CAS  PubMed  Google Scholar 

  11. J. Sinkkonen, V. Ovcharenko, K.N. Zelenin, I.P. Bezhan, B.A. Chakchir, F. Al Assar, K. Pihlaja, Eur. J. Org. Chem. 13, 2046 (2002)

    Google Scholar 

  12. C.K. Ryu, R.E. Park, M.Y. Ma, J.H. Nho, Bioorg. Med. Chem. Lett. 17, 2577 (2007)

    CAS  PubMed  Google Scholar 

  13. R.A. Izydore, I.H. Hall, Chem. Abstr. 112, 151876X (1990)

    Google Scholar 

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

    CAS  PubMed  Google Scholar 

  15. V.P. Litvinov, Russ. Chem. Rev. 72, 69 (2003)

    CAS  Google Scholar 

  16. L.J. Street, F. Sternfeld, R.A. Jelley, A.J. Reeve, R.W. Carling, K.W. Moore, R.M. Mc Kernan, B. Sohal, S. Cook, A. Pike, G.R. Dawson, F.A. Bromidge, K.A. Wafford, G.R. Seabrook, S.A. Thompson, G. Marshall, G.V. Pillai, J.L. Castro, J.R. Atack, A.M. Mac Leod, J. Med. Chem. 47, 3642 (2004)

    CAS  PubMed  Google Scholar 

  17. S. Mavel, I. Thery, A. Gueiffier, Arch. Pharm. Med. Chem. 335, 7 (2002)

    CAS  Google Scholar 

  18. A.D. Lebsack, J. Gunzner, B. Wang, R. Pracitto, H. Schaffhauser, A. Santini, J. Aiyar, R. Bezverkov, B. Munoz, W. Liu, S. Venkatraman, Bioorg. Med. Chem. Lett. 14, 2463 (2004)

    CAS  PubMed  Google Scholar 

  19. H. Wu, X.M. Chen, Y. Wan, H.Q. Xin, H.H. Xu, R. Ma, C.H. Yue, L.L. Pang, Lett. Org. Chem. 6, 219 (2009)

    CAS  Google Scholar 

  20. Y.K. Ramtohup, M.N.G. James, J.C. Vederas, J. Org. Chem. 67, 3169 (2002)

    Google Scholar 

  21. L.P. Liu, J.M. Lu, M. Shi, Org. Lett. 9, 1303 (2007)

    CAS  PubMed  Google Scholar 

  22. T. Sheradsky, R. Moshenberg, J. Org. Chem. 51, 3123 (1986)

    CAS  Google Scholar 

  23. A. Csampai, K. Kormendy, F. Ruff, Tetrahedron 47, 4457 (1991)

    CAS  Google Scholar 

  24. R. Fazaeli, H. Aliyan, N. Fazaeli, Open Catal. J. 3, 14 (2010)

    CAS  Google Scholar 

  25. H. Shaterian, A. Hosseinian, M. Ghashang, Arkivoc 2, 59 (2009)

    Google Scholar 

  26. A. Hasaninejed, M.R. Kazerooni, A. Zare, Catal. Today 196, 148 (2012)

    CAS  Google Scholar 

  27. H. Veisi, A.A. Manesh, N. Khankhani, R. Ghorbani-Vaghei, RSC Adv. 4, 25057 (2014)

    CAS  Google Scholar 

  28. H.R. Shaterian, M. Aghakhanizadeh, Comptes Rendus Chim. 15, 1060 (2012)

    CAS  Google Scholar 

  29. J.M. Khurana, D. Magoo, Tetrahedron Lett. 50, 7300 (2009)

    CAS  Google Scholar 

  30. M. Sayyafi, M. Seyyedhamzeh, H.R. Khavasi, A. Bazgir, Tetrahedron 64, 2375 (2008)

    CAS  Google Scholar 

  31. G. Shukla, R.K. Verma, G.K. Verma, M.S. Singh, Tetrahedron Lett. 52, 7195 (2011)

    CAS  Google Scholar 

  32. X. Wang, W.W. Ma, L.Q. Wu, F.L. Yan, J. Chin. Chem. Soc. 57, 1341 (2010)

    CAS  Google Scholar 

  33. M. Shekouhy, A. Hasaninejad, Ultrason. Sonochem. 19, 307 (2012)

    CAS  PubMed  Google Scholar 

  34. B. Atashkar, A. Rostami, H. Gholami, B. Tahmasbi, Res. Chem. Intermed. 41, 3675 (2015)

    CAS  Google Scholar 

  35. E. Mosaddegh, A. Hassankhani, Tetrahedron Lett. 52, 488 (2011)

    CAS  Google Scholar 

  36. M. Saha, S. Phukan, R. Jamatia, S. Mitra, A.K. Pal, RSC Adv. 3, 1714 (2013)

    CAS  Google Scholar 

  37. H.R. Shaterian, E. Mollashahi, A. Biabangard, J. Chem. Soc. Pak. 35, 329 (2013)

    Google Scholar 

  38. L.T.A. Sofia, A. Krishnan, M. Sankar, N.K. Kala Raj, P. Manikandan, P.R. Rajamohanan, T.G. Ajithkumar, J. Phys. Chem. C 113, 21114 (2009)

    CAS  Google Scholar 

  39. J. Javidi, M. Esmaeilpour, F.N. Dodeji, RSC Adv. 5, 308 (2015)

    CAS  Google Scholar 

  40. Z. Zhang, F. Zhang, Q. Zhu, W. Zhao, B. Ma, Y. Ding, J. Colloid Interface Sci. 360, 189 (2011)

    CAS  PubMed  Google Scholar 

  41. A. Afkhami, R. Norooz-Asl, Colloids Surf. A 346, 52 (2009)

    CAS  Google Scholar 

  42. J. Zhang, R.D.K. Misra, Acta Biomater. 3, 838 (2007)

    CAS  PubMed  Google Scholar 

  43. Y. Tai, L. Wang, G. Yan, J. Gao, H. Yua, L. Zhang, Polym. Int. 60, 976 (2011)

    CAS  Google Scholar 

  44. A. Ito, H. Jitsunobu, Y. Kawabe, H. Ijima, M. Kamihira, Tissue Eng. C 15, 413 (2009)

    CAS  Google Scholar 

  45. E. Taboada, R. Solanas, E. Rodriguez, R. Weissleder, A. Roig, Adv. Funct. Mater. 19, 2319 (2009)

    CAS  Google Scholar 

  46. J.L. Zhang, R.S. Srivastava, R.D.K. Misra, Langmuir 23, 6342 (2007)

    CAS  PubMed  Google Scholar 

  47. A.H. Lu, W. Schmidt, N. Matoussevitch, H. Bönnemann, B. Spliethoff, B. Tesche, E. Bill, W. Kiefer, F. Schuth, Angew. Chem. Int. Ed. 43, 4303 (2004)

    CAS  Google Scholar 

  48. Z. Lei, S. Bi, Mater. Lett. 61, 3531 (2007)

    CAS  Google Scholar 

  49. D. Zhang, S. Wei, C. Kaila, X. Su, J. Wu, A.B. Karki, D.P. Young, Z. Gue, Nanoscale 2, 917 (2010)

    CAS  PubMed  Google Scholar 

  50. J. Gu, W. Zhang, X. Yang, Mater. Lett. 94, 8 (2013)

    CAS  Google Scholar 

  51. Z. Sun, D. Liu, L. Tong, J. Shi, X. Yang, L. Yu, Y. Tao, H. Yang, Solid State Sci. 13, 361 (2011)

    CAS  Google Scholar 

  52. Q. Chang, L. Zhu, C. Yu, H. Tang, J. Lumin. 128, 1890 (2008)

    CAS  Google Scholar 

  53. M. Esmaeilpour, A.R. Sardarian, J. Javidi, Appl. Catal. A Gen. 445–446, 359 (2012)

    Google Scholar 

  54. M. Esmaeilpour, J. Javidi, F.N. Dodeji, M.M. Abarghoui, J. Mol. Catal. A: Chem. 393, 18 (2014)

    CAS  Google Scholar 

  55. J. Javidi, M. Esmaeilpour, Z. Rahiminezhad, F.N. Dodeji, J. Cluster Sci. 25, 1511 (2014)

    CAS  Google Scholar 

  56. M. Esmaeilpour, J. Javidi, M. Zandi, Mater. Res. Bull. 55, 78 (2014)

    CAS  Google Scholar 

  57. A. Davood, K. Seyed-Mola, N. Razieh, J. Chem. Sci. 126, 95 (2014)

    Google Scholar 

  58. M. Esmaeilpour, A.R. Sardarian, J. Javidi, J. Organomet. Chem. 749, 233 (2014)

    CAS  Google Scholar 

  59. M. Esmaeilpour, J. Javidi, F. Dehghani, F.N. Dodeji, New J. Chem. 39, 3388 (2015)

    CAS  Google Scholar 

  60. X.N. Zhao, G.F. Hu, M. Tang, T.T. Shi, X.L. Guo, T.T. Li, Z.H. Zhang, RSC Adv. 4, 51089 (2014)

    CAS  Google Scholar 

  61. R. Ghorbani-Vaghei, R. Karimi-Nami, Z. Toghraei-Semiromi, M. Amiri, M. Ghavidel, Tetrahedron 67, 1930 (2011)

    CAS  Google Scholar 

  62. M.V. Reddy, G.C.S. Reddy, Y.T. Jeong, Tetrahedron 68, 6820 (2012)

    Google Scholar 

  63. G. Sabitha, C. Srinivas, A. Raghavendar, J.S. Yadav, Helv. Chim. Acta 93, 1375 (2010)

    CAS  Google Scholar 

  64. L. Nagarapu, R. Bantu, H.B. Mereyala, J. Heterocycl. Chem. 46, 728 (2009)

    CAS  Google Scholar 

  65. H.R. Shaterian, F. Khorami, A. Amirzadeh, R. Doostmohammadi, M. Ghashang, J. Iran. Chem. Res 2, 57 (2009)

    Google Scholar 

  66. A.R. Kiasat, S. Noorizadeh, M. Ghahremani, S.J. Saghanejad, J. Mol. Struct. 1036, 216 (2013)

    CAS  Google Scholar 

  67. A.R. Kiasat, J. Davarpanah, J. Mol. Catal. A: Chem. 373, 46 (2013)

    CAS  Google Scholar 

  68. M.A. Zolfigol, M. Mokhlesi, S. Farahmand, J. Iran. Chem. Soc. 10, 577 (2013)

    CAS  Google Scholar 

  69. M. Kidwai, R. Chauhan, A. Jahan, Chin. Sci. Bull. 57, 2273 (2012)

    Google Scholar 

  70. M. Soheilizad, M. Adib, S. Sajjadifar, Monatsh. Chem. 145, 1353 (2014)

    CAS  Google Scholar 

  71. B. Maleki, S.S. Ashrafi, R. Tayebee, RSC Adv. 4, 41521 (2014)

    CAS  Google Scholar 

Download references

Acknowledgments

The authors are grateful to the council of Iran National Science Foundation and University of Shiraz for their unending effort to provide financial support to undertake this work.

Author information

Authors and Affiliations

  1. Chemistry Department, College of Science, Shiraz University, Shiraz, Iran

    Mohsen Esmaeilpour

  2. Department of Pharmaceutics, School of Pharmacy, Shahid Beheshti University of Medical Sciences, Tehran, Islamic Republic of Iran

    Jaber Javidi & Fatemeh Nowroozi Dodeji

  3. Students Research Committee, School of Pharmacy, Shahid Beheshti University of Medical Sciences, Tehran, Islamic Republic of Iran

    Jaber Javidi

  4. Department of Science, Payame Noor University (PNU), Tehran, Islamic Republic of Iran

    Saeed Zahmatkesh

Authors
  1. Mohsen Esmaeilpour
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Jaber Javidi
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Fatemeh Nowroozi Dodeji
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. Saeed Zahmatkesh
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding authors

Correspondence to Mohsen Esmaeilpour or Saeed Zahmatkesh.

Electronic supplementary material

Below is the link to the electronic supplementary material.

Supplementary material 1 (DOC 1134 kb)

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Esmaeilpour, M., Javidi, J., Dodeji, F.N. et al. Solvent-free, sonochemical, one-pot, four-component synthesis of 2H-indazolo[2,1-b]phthalazine-triones and 1H-pyrazolo[1,2-b]phthalazine-diones catalyzed by Fe3O4@SiO2-imid-PMAn magnetic nanoparticles. Res Chem Intermed 47, 2629–2652 (2021). https://doi.org/10.1007/s11164-016-2462-6

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s11164-016-2462-6

Keywords

Search

Navigation