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Catalysis of Indazolophthalazinetriones by Ionic Liquid – Succinimidinium Hydrogen Sulfate

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Theoretical and Experimental Chemistry Aims and scope

Succinimidinium hydrogen sulfate, a newly reported Brønsted acidic ionic liquid, is used as an efficient, homogeneous catalyst for synthesis of prospective API (active pharmaceutical ingredients) – 2H-indazolo[2,1-b]phthalazine-1,6,11(13H)-trione derivatives. Mild reaction conditions, short reaction times, high yields, and easy work-up of the products and catalyst are some of advantages of this protocol.

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References

  1. M. B. Gawande, P. S. Branco, and R. S. Varma, Chem. Soc. Rev., 42, 3371-3393 (2013).

    Article  CAS  Google Scholar 

  2. Takahiko Akiyama, Chem. Rev., 107, 5744-5758 (2007).

  3. E. C. Franklin, Chem. Rev., 16, 305-361 (1935).

    Article  CAS  Google Scholar 

  4. F. W. Bergstrom, Chem. Rev., 35, 77-277 (1944).

    Article  CAS  Google Scholar 

  5. S. Suzuki, K. Kataoka, and K. Kamaguchi, Acc. Chem. Res., 33, 728-735 (2000).

    Article  CAS  Google Scholar 

  6. V. P. Litvinov, Russ. Chem. Rev., 72, 69-85 (2003).

    Article  CAS  Google Scholar 

  7. C. Turk, J. Svete, B. Stanovnik, et al., Helv. Chim. Acta, 84, 146-156 (2001).

    Article  CAS  Google Scholar 

  8. J. S. Kim, H. K. Rhee, H. J. Park, et al., Bioorg. Med. Chem., 16, 4545-4550 (2008).

    Article  CAS  Google Scholar 

  9. R. Dua, S. Shrivastava, S. K. Sonwane, and S. K. Srivastava, Adv. Biol. Res., 5, 120-144 (2011).

    CAS  Google Scholar 

  10. X. Y. Sun, C. X. Wei, X. Q. Deng, et al., Pharm. Rep., 62, 273-277 (2010).

    Article  CAS  Google Scholar 

  11. M. Asif, Curr. Med. Chem., 19, 2984-2991 (2012).

    Article  CAS  Google Scholar 

  12. F. M. Awadallah, W. I. EI-Eraky, and D. O. Saleh, Eur. J. Med. Chem., 52, 14-21 (2012).

    Article  CAS  Google Scholar 

  13. Y. Nomoto, H. Obase, H. Takei, et al., Chem. Pharm. Bull. (Tokyo), 38, 2179-2183 (1990).

  14. N. Watanabe, Y. Kabasawa, Y. Takase, et al., J. Med. Chem., 41, 3367-3372 (1998).

    Article  CAS  Google Scholar 

  15. J. S. Kim, H. K. Rhee, H. J. Park, et al., Bioorg. Med. Chem., 16, 4545-4550 (2008).

    Article  CAS  Google Scholar 

  16. S. S. El-Sakka, A. H. Soliman, and A. M. Imam, Afinidad, 66, 167-172 (2009).

    CAS  Google Scholar 

  17. C. K. Ryu, R. E. Park, M. Y. Ma, and J. H. Nho, Bioorg. Med. Chem. Lett., 17, 2577-2580 (2007).

    Article  CAS  Google Scholar 

  18. J. Li, Y. F. Zhao, X. Y. Yuan, et al., Molecules, 11, 574-582 (2006).

    Article  CAS  Google Scholar 

  19. J. Sinkkonen, V. Ovcharenko, K. N. Zelenin, et al., Eur. J. Org. Chem., 13, 2046-2053 (2002).

    Article  Google Scholar 

  20. S. Grasso, G. DeSarro, N. Micale, et al., J. Med. Chem., 43, 2851-2859 (2000).

    Article  CAS  Google Scholar 

  21. H. Wu, X. M. Chen, Y. Wan, et al., Lett. Org. Chem., 6, 219-223 (2009).

    Article  CAS  Google Scholar 

  22. J. E. R. Nascimento, D. H. de Oliveira, P. B. Abib, et al., J. Braz. Chem. Soc., 26, 1533-1541 (2015).

    CAS  Google Scholar 

  23. X. Wang, W. W. Ma, L. Q. Wu, and F. L. Yan, J. Chin. Chem. Soc., 57, 1341-1345 (2010).

    CAS  Google Scholar 

  24. H. R. Shaterian, F. Khorami, A. Amirzadeh, et al., J. Iran. Chem. Res., 2, 57-62 (2009).

    Google Scholar 

  25. A. Varghese, A. Nizam, R. Kulkarni, and L. George, Eur. J. Chem., 4, 132-140 (2013).

    Article  CAS  Google Scholar 

  26. J. M. Khurana and D. Magoo, Tetrahedron Lett., 50, 7300-7303 (2009).

    Article  CAS  Google Scholar 

  27. K. Mazaahir, C. Ritika, and K. Anwar, Chin. Sci. Bull., 57, 2273-2279 (2012).

    Article  CAS  Google Scholar 

  28. H. R. Shaterian, A. Hosseinian, and M. Ghashang, ARKIVOCii, 59-67 (2009).

  29. M. Sayyafi, M. Seyyed Hamzeh, H. R. Khavasi, and A. Bazgir, Tetrahedron, 64, 2375-2378 (2008).

    Article  CAS  Google Scholar 

  30. A. Gharib, B. R. H. Khorasani, M. Jahangir, and J. H. W. Scheeren, Bulg. Chem. Commun., 45, 64-70 (2013).

    CAS  Google Scholar 

  31. A. Khazaei, M. A. Zolfigol, T. Faal-Rastegar, et al., Iran. J. Catal., 3, 211-220 (2013).

    CAS  Google Scholar 

  32. P. Wasserscheid and T. Welton, Ionic Liquids in Synthesis, VCH, Weinheim (2003).

    Google Scholar 

  33. J. Feng, L.Ying-jie, D. Hai-feng, et al., Chem. Res. Chin. Univ., 26, 384-388 (2010).

  34. F. Shirini, O. G. Jolodar, M. Seddighi, and H. Takbiri Borujeni, RSC Adv., 5, 19790-19798 (2015).

    Article  CAS  Google Scholar 

  35. F. Shirini and O. G. Jolodar, J. Mol. Catal. A, 356, 61-69 (2012).

    Article  CAS  Google Scholar 

  36. F. Shirini, M. Mamaghani, and M. Seddighi, Catal. Commun., 36, 31-37 (2013).

    Article  CAS  Google Scholar 

  37. F. Shirini and N. Gh. Khaligh, J. Mol. Liq., 177, 386-393 (2013).

    Article  CAS  Google Scholar 

  38. O. G. Jolodar, F. Shirini, and M. Seddighi, RSC Adv., 6, 44794-44806 (2016).

    Article  Google Scholar 

  39. F. Shirini, P. N. Moghadam, S. Moayediab, and M. Seddighi, RSC Adv., 4, 38581-38588 (2014).

    Article  CAS  Google Scholar 

  40. L. Pisano, L. Degennaro, M. Carraro, et al., Eur. J. Org. Chem., 19, 3252-3258 (2016).

    Article  Google Scholar 

  41. M. J. Frisch, et al., Gaussian-03 ed., Gaussian, Inc., Wallingford, CT (2003).

  42. A. R. Kiasat, S. Nourizadeh, M. Ghahremani, and S. J. Sagha Nejad, J. Mol. Struct., 1036, 216-225 (2013).

    CAS  Google Scholar 

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We are thankful to the University of Guilan Research Council for partial support of this work.

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Translated from Teoreticheskaya i Éksperimental’naya Khimiya, Vol. 52, No. 6, pp. 348-355, November-December, 2016.

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Goli-Jolodar, O., Shirini, F. Catalysis of Indazolophthalazinetriones by Ionic Liquid – Succinimidinium Hydrogen Sulfate. Theor Exp Chem 52, 349–357 (2017). https://doi.org/10.1007/s11237-017-9489-7

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  • DOI: https://doi.org/10.1007/s11237-017-9489-7

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