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Sulfanilic acid functionalized mesoporous SBA-15: A water-tolerant solid acid catalyst for the synthesis of uracil fused spirooxindoles as antioxidant agents

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Abstract

Incorporating sulfanilic acid as a hydrophobic Brønsted acid inside the nanospaces of SBA-15 led to a water-tolerant solid acid catalyst, SBA-15-PhSO3H, which showed excellent catalytic performance in synthesis of uracil-fused spirooxindoles in aqueous ethanol. The synthesized compounds were evaluated for their antioxidant activity by 1,1-diphenyl-2-picrylhydrazyl (DPPH) radical-scavenging assay.

Green synthesis of uracil-fused spirooxindoles using sulfanilic acidfunctionalized SBA-15 as a reusable heterogeneous acid catalyst and the antioxidant activity of the synthesized compounds are described.

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References

  1. (a) Kefayati H, Narchin F and Rad-Moghadam K 2012 Tetrahedron Lett. 53 4573; (b) Kumar M, Sharma K and Arya A K 2012 Tetrahedron Lett. 53 4604; (c) Arya A K, Gupta S K and Kumar M 2012 Tetrahedron Lett. 53 6035; (d) Zhu J and Bienayme H 2005 In Multicomponent Reactions (Weinheim: Wiley-VCH)

  2. Clark J H and Macquarrie D J 1996 Chem. Soc. Rev. 25 303

    Article  CAS  Google Scholar 

  3. Adam F, Hello K M and Aisha M R B 2011 J. Taiwan Inst. Chem. E 42 843

    Article  CAS  Google Scholar 

  4. (a) Martin-Aranda R M and Cejka J 2010 Top. Catal. 53 141; (b) Mondal J, Nandi M, Modak A and Bhaumik A 2012 J. Molecul. Catal. A 363–364 254

  5. Karimi B and Zareyee D 2008 Org. Lett. 10 3989

    Article  CAS  Google Scholar 

  6. Karimi B and Vafaeezadeh M 2012 Chem. Commun. 48 3327

    Article  CAS  Google Scholar 

  7. Yuan C, Huang Z and Chen J 2012 Catal. Commun. 24 56

    Article  CAS  Google Scholar 

  8. Parvin M N, Jin H, Ansari M B, Oh S M and Park S E 2012 Appl. Catal. A 413-414 205

    Article  CAS  Google Scholar 

  9. Mohammadi Ziarania G, Mousavi S, Lashgari N and Badiei A 2013 J. Chem. Sci. 125 1359

    Article  Google Scholar 

  10. Rostamnia S, Xin H, Liuc X and Lamei K 2013 J. Molecul. Catal. A 374–375 85

    Article  Google Scholar 

  11. Zareyee D, Moosavi S M and Alaminezhad A 2013 J. Molecul. Catal. A 378 227

    Article  CAS  Google Scholar 

  12. Rostamnia S and Hassankhani A 2014 Synlett 25 2753

    Article  CAS  Google Scholar 

  13. Mohammadi Ziarania G, Lashgari N and Badiei A 2015 J. Molecul. Catal. A 397 166

    Article  Google Scholar 

  14. Bahrami K, Khodaei M M and Fattahpour P 2015 J. Chem. Sci. 127 167

    Article  CAS  Google Scholar 

  15. Abdel-Rahman A H, Keshk E M, Hanna M A and El-Bady S M 2004 Bioorg. Med. Chem. 12 2483

    Article  CAS  Google Scholar 

  16. Kornet M J and Thio A P 1976 J. Med. Chem. 19 892

    Article  CAS  Google Scholar 

  17. Okita T and Isobe M 1994 Tetrahedron 50 11143

    Article  CAS  Google Scholar 

  18. Rosenmond P, Hosseini-Merescht M and Bub C 1994 Liebigs Ann. Chem. 2 151

    Article  Google Scholar 

  19. Usui T, Kondoh M, Cui C B, Mayumi T and Osada H 1998 Biochem. J. 333 543

    Article  CAS  Google Scholar 

  20. Kang T H, Matsumoto K, Murakami Y, Takayama H, Kitajima M, Aimi N and Watanabe H 2002 Eur. J. Pharmacol. 444 39

    Article  CAS  Google Scholar 

  21. Litvinov Y M, Mortikov V Y and Shestopalov A M 2008 J. Comb. Chem. 10 741

    Article  CAS  Google Scholar 

  22. Ghahremanzadeh R, Sayyafi M, Ahadi S and Bazgir A 2009 J. Comb. Chem. 11 393

    Article  CAS  Google Scholar 

  23. Ghahremanzadeh R, Imani Shakibaei G, Ahadi S and Bazgir A 2010 J. Comb. Chem. 12 191

    Article  CAS  Google Scholar 

  24. Balamurugan K, Perumal S and Menendez J C 2011 Tetrahedron 67 3201

    Article  CAS  Google Scholar 

  25. Imani Shakibaei G, Feiz A, Khavasi H R, Abolhasani Soorki A and Bazgir A 2011 ACS Comb. Sci. 13 96

    Article  Google Scholar 

  26. Jadidi K, Ghahremanzadeh R, Mirzaei P and Bazgir A 2011 J. Heterocycl. Chem. 48 1014

    Article  CAS  Google Scholar 

  27. Arya A K and Kumar M 2011 Mol. Divers. 15 781

    Article  CAS  Google Scholar 

  28. Kumar M, Sharma K and Arya A K 2012 Tetrahedron Lett. 53 4604

    Article  CAS  Google Scholar 

  29. Rahmati A and Khalesi Z 2012 Tetrahedron 68 8472

    Article  CAS  Google Scholar 

  30. Paul S and Das A R 2013 Tetrahedron Lett. 54 1149

    Article  CAS  Google Scholar 

  31. Khalafi-Nezhad A and Mohammadi S 2013 ACS Comb. Sci. 15 512

    Article  CAS  Google Scholar 

  32. Baharfar R and Azimi R 2014 Synth. Commun. 44 89

    Article  CAS  Google Scholar 

  33. Baharfar R and Shariati N 2014 Aust. J. Chem. 67 1646

    Article  CAS  Google Scholar 

  34. Azimi R and Baharfar R 2014 Can. J. Chem. 92 1163

    Article  CAS  Google Scholar 

  35. Adam F, Hello K M and Ali T H 2011 Appl. Catal. A 399 42

    Article  CAS  Google Scholar 

  36. Blois M S 1958 Nature 26 1199

    Article  Google Scholar 

  37. Kumar M, Sharma K, Samarth R M and Kumar A 2010 Eur. J. Med. Chem. 45 4467

    Article  CAS  Google Scholar 

  38. Kadhum A A H, Al-Amiery A A, Musa A Y and Mohamad A B 2011 Int. J. Mol. Sci. 12 5747

    Article  CAS  Google Scholar 

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Acknowledgements

We are thankful to the Research Council of Mazandaran University for the financial support of this work.

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Correspondence to ROBABEH BAHARFAR.

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Supplementary Information

All additional information relating to characterization of the catalyst using FT-IR, TGA, XRD and TEM techniques (figures S1–S4), 1H NMR and 13C NMR spectra for compounds 4a-j (figures S5-S24) are available in the supplementary information, which is available free of charge at www.ias.ac.in/chemsci.

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BAHARFAR, R., AZIMI, R. Sulfanilic acid functionalized mesoporous SBA-15: A water-tolerant solid acid catalyst for the synthesis of uracil fused spirooxindoles as antioxidant agents. J Chem Sci 127, 1389–1395 (2015). https://doi.org/10.1007/s12039-015-0910-2

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  • DOI: https://doi.org/10.1007/s12039-015-0910-2

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