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p-TSA-catalyzed synthesis of spiroquinazolinones

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Abstract

p-Toluene sulfonic acid-catalyzed one-pot reaction of anthranilamide with ketones resulted in very good yields of novel spiroquinazolinones. The reaction worked well with a wide variety of ketones in shorter reaction times. The products were characterized using different spectral techniques.

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References

  1. D.L. Dreyer, R.C. Brenner, Phytochemistry 19, 935 (1980)

    Article  CAS  Google Scholar 

  2. V. Alagarsamy, V.R. Solomon, K. Dhanabal, Bioorg. Med. Chem. 15, 235 (2007)

    Article  CAS  Google Scholar 

  3. V. Alagarsamy, U.S. Pathak, Bioorg. Med. Chem. 15, 3457 (2007)

    Article  CAS  Google Scholar 

  4. V. Murugan, M. Kulkarni, R.M. Anand, E.P. Kumar, B. Suresh, V.M. Reddy, Asian J. Chem. 18, 900 (2006)

    CAS  Google Scholar 

  5. A.A.A. Godfrey, PCT Int. Appl. WO 2005012260 A2, Chem. Abstr. 142, 198095 (2005)

    Google Scholar 

  6. J. Imagawa, K. Sakai, Eur. J. Pharmacol. 131, 257 (1986)

    Article  CAS  Google Scholar 

  7. R.O. Dempcy, E.B. Skibo, Biochemistry 30, 8480 (1991)

    Article  CAS  Google Scholar 

  8. S.L. Gackenheimer, J.M. Schaus, D.R. Gehlert, J. Pharmacol. Exp. Ther. 274, 1558 (1995)

    CAS  Google Scholar 

  9. P. Selvam, K. Girija, G. Nagarajan, E. De Clerco, Indian J. Pharm. Sci. 67, 484 (2005)

    CAS  Google Scholar 

  10. W.K. Su, B.B. Yang, Aust. J. Chem. 55, 695 (2002)

    Article  CAS  Google Scholar 

  11. W.K. Su, B.B. Yang, J. Chem. Res., Synop. 5, 604 (2002)

    Article  Google Scholar 

  12. D.Q. Shi, L.C. Rong, J.X. Wang, X.S. Wang, S.J. Tu, H.W. Hu, Chem. J. Chin. Univ. 25, 2051 (2004)

    CAS  Google Scholar 

  13. D.Q. Shi, J.X. Wang, L.C. Rong, Q.Y. Zhuang, S.J. Tu, H.W. Hu, J. Chem. Res., Synop. 10, 671 (2003)

    Article  Google Scholar 

  14. D.Q. Shi, C.L. Shi, J.X. Wang, L.C. Rong, Q.Y. Zhuang, X.S. Wang, J. Heterocyclic Chem. 40, 173 (2005)

    Article  Google Scholar 

  15. A. Shaabani, A. Ali Maleki, H. Mofakham, Synth. Commun. 38, 3751 (2008)

    Article  CAS  Google Scholar 

  16. B.A. Bhat, D.P. Sahu, Synth. Commun. 34, 2169 (2004)

    Article  CAS  Google Scholar 

  17. G.W. Wang, C.B. Miao, H. Kang, Bull. Chem. Soc. Jpn 79, 1426 (2006)

    Article  CAS  Google Scholar 

  18. R.J. Abdel Jalil, W. Voelter, M. Saeed, Tetrahedron Lett. 45, 3475 (2004)

    Article  CAS  Google Scholar 

  19. D.Q. Shi, L.C. Rong, J.X. Wang, Q.Y. Zhuang, X.S. Wang, H.W. Hu, Tetrahedron Lett. 44, 3199 (2003)

    Article  CAS  Google Scholar 

  20. X. Cheng, S. Vellalath, R. Goddard, B. List, J. Am. Chem. Soc. 130, 15786 (2008)

    Article  CAS  Google Scholar 

  21. M. Rueping, A.P. Antonchick, E. Sugiono, K. Grenader, Angew. Chem. Int. Ed. 48, 908 (2009)

    Article  CAS  Google Scholar 

  22. J. Chen, W. Su, H. Wu, M. Liu, C. Jin, Green Chem. 9, 972 (2007)

    Article  CAS  Google Scholar 

  23. S. Hamid Reza, O. Ali Reza, Chin. J. Chem. 27, 2418 (2009)

    Article  Google Scholar 

  24. J.X. Chen, H.Y. Wu, W.K. Su, Chin. Chem. Lett. 18, 536 (2007)

    Article  CAS  Google Scholar 

  25. J. Chen, D. Wu, F. He, M. Liu, H. Wu, J. Ding, W. Su, Tetrahedron Lett. 49, 3814 (2008)

    Article  CAS  Google Scholar 

  26. M. Wang, T. Ting Zhang, Y. Liang, J. Jing Gao, Chin. Chem. Lett. 22, 1423 (2011)

    Article  CAS  Google Scholar 

  27. M. Abdollahi-Alibeik, E. Shabani, Chin. Chem. Lett. 22, 1163 (2011)

    CAS  Google Scholar 

  28. Y.X. Zong, Y. Zhao, W.C. Luo, X. Hai, Yu, J. Ke Wang, Y. Pan. Chin. Chem. Lett. 21, 778 (2010)

    Article  CAS  Google Scholar 

  29. K. Kumari, D.S. Raghuvanshi, K. Nand Singh, Indian J. Chem. 51B, 860 (2012)

    CAS  Google Scholar 

  30. P. Salehi, M. Dabiri, M. Baghbanzadeh, M. Bahramnejad, Synth. Commun. 36, 2287 (2006)

    Article  CAS  Google Scholar 

  31. Y. Chen, W. Shan, M. Lei, L. Hu, Tetrahedron Lett. 53, 5923 (2012)

    Article  CAS  Google Scholar 

  32. S. Khaksar, S. Mohammadzadeh Talesh, CR Chimie 15, 779 (2012)

    Article  CAS  Google Scholar 

  33. K. Niknam, N. Jafarpour, E. Niknam, Chin. Chem. Lett. 22, 69 (2011)

    Article  CAS  Google Scholar 

  34. A.A. Mohammadi, M. Dabiri, H. Qarat, Tetrahedron 65, 3804 (2009)

    Article  CAS  Google Scholar 

  35. K. Niknam, M.R. Mohammadizadeh, S. Mirzaee, Chin. J. Chem. 29, 1417 (2011)

    Article  CAS  Google Scholar 

  36. F. Li, Y. Feng, Q. Meng, W. Li, Z. Li, Q. Wang, F. Tao, Arkivoc i, 40 (2007)

    Google Scholar 

  37. Y. Hu, M.M. Wang, H. Chen, D.Q. Shi, Tetrahedron 67, 9342 (2011)

    Article  CAS  Google Scholar 

  38. M. Dabiri, A.A. Mohammadi, H. Qarat, Monatsh. Chem. 140, 401 (2009)

    Article  CAS  Google Scholar 

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Acknowledgments

The authors are grateful to Prof. M. Periasamy and the UGC Networking Resource Centre, University of Hyderabad, India, for providing the spectral facilities. K. R. thanks Jawaharlal Nehru Memorial Fund for the financial support for doctoral studies.

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Authors and Affiliations

  1. Department of Chemistry, Periyar University, Salem, 636011, Tamil Nadu, India

    Krishnan Revathy & Appaswami Lalitha

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  1. Krishnan Revathy
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  2. Appaswami Lalitha
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Correspondence to Appaswami Lalitha.

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Revathy, K., Lalitha, A. p-TSA-catalyzed synthesis of spiroquinazolinones. J IRAN CHEM SOC 12, 2045–2049 (2015). https://doi.org/10.1007/s13738-015-0680-2

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  • DOI: https://doi.org/10.1007/s13738-015-0680-2

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