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Sulfuric acid-modified poly(ethylene glycol): an efficient, biodegradable, and reusable polymeric catalyst for synthesis of spiro oxindole derivatives in aqueous medium

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Abstract

A versatile, novel, and environmentally benign strategy has been successfully developed for synthesis of oxindoles, an important class of potentially bioactive compounds. Sulfonated poly(ethylene glycol) was used as inexpensive and recyclable acidic catalyst. The products were obtained in water, an excellent solvent in terms of environmental impact, in high yield, by one-pot reaction of malononitrile, 1,3-dicarbonylcoumarin or 4-hydroxycoumarin derivatives, and isatins. This new method totally avoids the use of organic acids and toxic or expensive solvents.

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References

  1. R. de Miguel, Yolanda, J. Chem. Soc. Perkin Trans. 1, 4213 (2000)

    Google Scholar 

  2. P. Vivek, S.V. Rajender, Green Chem. 12, 743 (2010)

    Article  Google Scholar 

  3. X. Wang, Z. Quan, F. Wang, M. Wang, Z. Zhang, Z. Lia, Synth. Commun. 36, 451 (2006)

    Article  CAS  Google Scholar 

  4. M.A. Nasseri, S.A. Alavi, B. Zakerinasab, J. Chem. Sci. 125, 109 (2013)

    Article  CAS  Google Scholar 

  5. A. Hasaninejad, A. Zare, M. Shekouhy, J. Ameri-Rad, Green Chem. 13, 958 (2011)

    Article  CAS  Google Scholar 

  6. C.B. Reddy, K.S. Kumar, M.A. Kumar, M.V. Narayana Reddy, B.S. Krishna, M. Naveen, M.K. Arunasree, C.S. Reddy, C.N. Raju, C.D. Reddy, Eur. J. Med. Chem. 47, 553 (2012)

    Article  CAS  Google Scholar 

  7. X.C. Wang, L. Li, Z. Zhang, J.Q. Zheng, Chin. Chem. Lett. 23, 423 (2012)

    Article  CAS  Google Scholar 

  8. M.A. Zolfigol, A. Khazaei, A. Zare, M. Mokhlesi, T. Hekmat zadeh, A. Hasaninejad, F. Derakhshan Panah, A.R. Moosavi Zare, H. Keypour, A.A. Dehghani Firouzabadi, M. Merajoddin, J. Chem. Sci. 124, 501 (2012)

    Article  CAS  Google Scholar 

  9. R.J. Sundberg, The Chemistry of Indoles (Academic Press, New York, 1996)

    Google Scholar 

  10. K.C. Joshi, P. Chand, Pharmazie. 37, 1 (1982)

    CAS  Google Scholar 

  11. A.H. Abdel-Rahman, E.M. Keshk, M.A. Hanna, Sh.M El-Bady, Bioorg. Med. Chem. 12, 2483 (2004)

    Article  CAS  Google Scholar 

  12. T.H. Kang, K. Matsumoto, M. Tohda, Y. Murakami, H. Takayama, M. Kitajima, N. Aimi, H. Watanabe, Eur. J. Pharmacol. 444, 39 (2002)

    Article  CAS  Google Scholar 

  13. J. Leclercq, M.C. De Pauw Gillet, R. Bassleer, L. Angenot, J. Ethnopharmacol. 15, 305 (1986)

    Article  CAS  Google Scholar 

  14. J. Ma, S. Hecht, M. Javaniside, Chem. Commun. 10, 1190 (2004)

    Article  Google Scholar 

  15. G.S. Singh, Z.Y. Desta, Chem. Rev. 112, 6104 (2012)

    Article  CAS  Google Scholar 

  16. B. Tan, N.R. Candeias, C.F. Barbas, Nat. Chem. 3, 473 (2011)

    CAS  Google Scholar 

  17. F. Shi, Z.L. Tao, S.W. Luo, S.J. Tu, L.Z. Gong, Chem. Eur. J. 18, 6885 (2012)

    Article  CAS  Google Scholar 

  18. F. Shi, R.Y. Zhu, X. Liang, S.J. Tu, Adv. Synth. Catal. 355, 2447 (2013)

    Article  CAS  Google Scholar 

  19. S. Pepeljnjak, I. Jalsenjak, D. Maysinger, Pharmazie. 37, 864 (1982)

    CAS  Google Scholar 

  20. B.E. Evans, K.E. Rittle, M.G. Bock, R.M. DiPardo, R.M. Freidinger, W.L. Whitter, G.F. Lundell, D.F. Veber, P.S. Anderson, R.S. Chang, J. Med. Chem. 31, 2235 (1988)

    Article  CAS  Google Scholar 

  21. L.L. Andreani, E. Lapi, Boll. Chim. Farm. 99, 583 (1960)

    Google Scholar 

  22. L. Bonsignore, G. Loy, D. Secci, Eur. J. Med. Chem. 28, 517 (1993)

    Article  CAS  Google Scholar 

  23. C.J. Li, Chem. Rev. 105, 3095 (2005)

    Article  CAS  Google Scholar 

  24. F. Bazi, H. El Badaoui, S. Tamani, S. Sokori, A. Solhy, D.J. Macquarrie, S. Sebti, Appl. Catal. A 211, 301 (2006)

    Google Scholar 

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Acknowledgments

We gratefully acknowledge support of this work by the University of Birjand research council.

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Authors and Affiliations

  1. Department of Chemistry, College of Sciences, University of Birjand, 97175-615, Birjand, Islamic Republic of Iran

    M. A. Nasseri & B. Zakerinasab

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  1. M. A. Nasseri
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  2. B. Zakerinasab
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Correspondence to M. A. Nasseri.

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Nasseri, M.A., Zakerinasab, B. Sulfuric acid-modified poly(ethylene glycol): an efficient, biodegradable, and reusable polymeric catalyst for synthesis of spiro oxindole derivatives in aqueous medium. Res Chem Intermed 41, 5261–5270 (2015). https://doi.org/10.1007/s11164-014-1627-4

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  • DOI: https://doi.org/10.1007/s11164-014-1627-4

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