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Application of SBA-Pr-SO3H as a nanoreactor in the one-pot synthesis of spiroquinazolinones

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Abstract

An efficient method for the synthesis of spiroquinazolinones was developed using isatoic anhydride, hydrazides and cyclic ketones, through a rapid one-pot three-component reaction in the presence of SBA-Pr-SO3H under solvent-free conditions. SBA-Pr-SO3H was an efficient heterogeneous nanoreactor with a pore size of 6 nm which can be easily handled and removed from the reaction mixture by simple filtration and can be reused several times without any loss of activity. The main advantages of using this nanoreactor are high product yields, being environmentally benign, short reaction times, and easy handling.

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References

  1. P.S. Reddy, P.P. Reddy, T. Vasantha, Heterocycles 60, 183 (2003)

    Article  CAS  Google Scholar 

  2. S.B. Mhaske, N.P. Argade, Tetrahedron 62, 9787 (2006)

    Article  CAS  Google Scholar 

  3. M. Sharma, K. Chauhan, R. Shivahare, P. Vishwakarma, M.K. Suthar, A. Sharma, S. Gupta, J.K. Saxena, J. Lal, P. Chandra, B. Kumar, P.M.S. Chauhan, J. Med. Chem. 56, 4374 (2013)

    Article  CAS  Google Scholar 

  4. G.M. Chinigo, M. Paige, S. Grindrod, E. Hamel, S. Dakshanamurthy, M. Chruszcz, W. Minor, M.L. Brown, J. Med. Chem. 51, 4620 (2008)

    Article  CAS  Google Scholar 

  5. A. Kamal, E.V. Bharathi, J.S. Reddy, M.J. Ramaiah, D. Dastagiri, M.K. Reddy, A. Viswanath, T.L. Reddy, T.B. Shaik, S.N.C.V.L. Pushpavalli, M.P. Bhadra, Eur. J. Med. Chem. 46, 691 (2011)

    Article  CAS  Google Scholar 

  6. Y. Zhou, Q. Feng, F. Di, Q. Liu, D. Wang, Y. Chen, L. Xiong, H. Song, Y. Li, Z. Li, Bioorg. Med. Chem. 21, 4968 (2013)

    Article  CAS  Google Scholar 

  7. T.O. Larsen, H. Franzyk, S.R. Jensen, J. Nat. Prod. 62, 1578 (1999)

    Article  CAS  Google Scholar 

  8. D. Zhao, J. Feng, Q. Huo, N. Melosh, G.H. Fredrickson, B.F. Chmelka, G.D. Stucky, Science 279, 548 (1998)

    Article  CAS  Google Scholar 

  9. D. Zhao, Q. Huo, J. Feng, B.F. Chmelka, G.D. Stucky, J. Am. Chem. Soc. 120, 6024 (1998)

    Article  CAS  Google Scholar 

  10. K. Bahrami, M.M. Khodaei, P. Fattahpour, Catal. Sci. Technol. 1, 389 (2011)

    Article  CAS  Google Scholar 

  11. S. Fiorilli, B. Onida, B. Bonelli, E. Garrone, J Phys Chem B 109, 16725 (2005)

    Article  CAS  Google Scholar 

  12. B. Karimi, E. Badreh, Org. Biomol. Chem. 9, 4194 (2011)

    Article  CAS  Google Scholar 

  13. B. Karimi, M. Vafaeezadeh, Chem. Commun. 48, 3327 (2012)

    Article  CAS  Google Scholar 

  14. A.S. Maria Chong, X.S. Zhao, J. Phys. Chem. B. 107, 12650 (2003)

    Article  Google Scholar 

  15. P. Gholamzadeh, G. Mohammadi Ziarani, A. Badiei, A. Abolhassani Soorki, N. Lashgari, Res. Chem. Intermed. 39, 3925 (2013)

    Article  CAS  Google Scholar 

  16. P. Gholamzadeh, G.M. Ziarani, A. Badiei, Z. Bahrami, Eur. J. Chem. 3, 279 (2012)

    Article  CAS  Google Scholar 

  17. N. Lashgari, G. Mohammadi Ziarani, A. Badiei, M. Zarezadeh-Mehrizi, J. Heterocycl. Chem. 51, 1628 (2014)

    Article  CAS  Google Scholar 

  18. G. Mohammadi Ziarani, A. Badiei, Y. Khaniania, M. Haddadpour, Iran J. Chem. Chem. Eng. 29, 1 (2010)

    Google Scholar 

  19. G. Mohammadi Ziarani, A. Badiei, S. Mousavi, N. Lashgari, A. Shahbazi, Chin. J. Catal. 33, 1832 (2012)

    Article  CAS  Google Scholar 

  20. G. Mohammadi Ziarani, N. Lashgari, A. Badiei, J. Mol. Catal. A: Chem. 397, 166 (2015)

    Article  CAS  Google Scholar 

  21. G. Mohammadi Ziarani, N. Lashgari, A.R. Badiei, Sci. Iran. 20, 580 (2013)

    Google Scholar 

  22. G. Mohammadi Ziarani, N.H. Mohtasham, A. Badiei, N. Lashgari, J. Chin. Chem. Soc. 61, 990 (2014)

    Article  Google Scholar 

  23. G. Mohammadi Ziarani, R. Moradi, A. Badiei, N. Lashgari, B. Moradi, A.A. Soorki, J. Taibah, Univ. Sci. 9, 555 (2015)

    Google Scholar 

  24. M. Tajbakhsh, S. Ramezanpour, S. Balalaie, H.R. Bijanzadeh, J. Heterocycl. Chem. 52, 1559 (2015)

    Article  CAS  Google Scholar 

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Acknowledgments

We gratefully acknowledge the financial support from the Research Council of Alzahra University and the University of Tehran. Partial support of this work by the K. N. Toosi University of Technology Research Council is appreciatively acknowledged.

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Authors and Affiliations

  1. Department of Chemistry, Alzahra University, Vanak Squqre, Tehran, Iran

    Vaezeh Fathi Vavsari & Ghodsi Mohammadi Ziarani

  2. School of Chemistry, College of Science, University of Tehran, Tehran, Iran

    Alireza Badiei

  3. Peptide Chemistry Research Center, K. N. Toosi University of Technology, Tehran, 15875-4416, Iran

    Saeed Balalaie

Authors
  1. Vaezeh Fathi Vavsari
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  2. Ghodsi Mohammadi Ziarani
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  3. Alireza Badiei
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  4. Saeed Balalaie
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Correspondence to Ghodsi Mohammadi Ziarani.

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Fathi Vavsari, V., Mohammadi Ziarani, G., Badiei, A. et al. Application of SBA-Pr-SO3H as a nanoreactor in the one-pot synthesis of spiroquinazolinones. J IRAN CHEM SOC 13, 1037–1043 (2016). https://doi.org/10.1007/s13738-016-0817-y

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