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Journal of the Iranian Chemical Society

, Volume 16, Issue 3, pp 603–608 | Cite as

Cu-catalyzed synthesis of functionalized benzo [1, 3] selenazin from intramolecular C–H activation reactions of isocyanides, aniline-acyl isoselenocyanate adduct

  • Manijeh Nematpour
  • Elham Rezaee
  • Mehdi Jahani
  • Sayyed Abbas TabatabaiEmail author
Original Paper
  • 12 Downloads

Abstract

A novel approach to the synthesis of benzo [1, 3] selenazin derivatives via a one-pot, four-component, intramolecular C–H activation reaction of isocyanides, aniline and acyl isoselenocyanate (generated from acyl chlorides and potassium selenocyanate) is presented. The reaction takes place under mild conditions in the presence of copper (I) iodide in acetone at room temperature with appropriate yields.

Graphical abstract

Keywords

C–H activation Cu catalyzed Benzo [1, 3] selenazin Isocyanides Acyl isoselenocyanate Aniline 

Notes

Acknowledgements

This work was supported by the Research Council of Shahid Beheshti University of Medical Sciences.

References

  1. 1.
    D.L. Klayman, W.H.H. Günther, Organic Selenium Compounds: Their Chemistry and Biology (Wiley, New York, 1973)Google Scholar
  2. 2.
    V.P. Litvinov, V.D. Dyachenko, Russ. Chem. Rev. 66, 923 (1997)CrossRefGoogle Scholar
  3. 3.
    A. Krief, L. Hevesi, Organoselenium Chemistry I (Springer Verlag, Berlin, Heidelberg, 1988)CrossRefGoogle Scholar
  4. 4.
    M. Renson, The Chemistry of Organic Selenium and Tellurium Compounds, vol 1, eds. by S. Patai, Z. Rappoport (Wiley, New York, 1986)Google Scholar
  5. 5.
    C. Paulmier, Selenium Reagents and Intermediates in Organic Synthesis (Pergamon Press, Oxford, 1986)Google Scholar
  6. 6.
    R.J. Shamberger, Biochemistry of Selenium (Plenum Press, New York, 1983)CrossRefGoogle Scholar
  7. 7.
    R.A. Passwaters, Selenium as Food and Medicine (Pivot Original Press, New Canaan, 1980)Google Scholar
  8. 8.
    Y. Ogasawara, G. Lacourciere, T.C. Stadtman, Proc. Natl. Acad. Sci. USA. 98, 9494 (2001)CrossRefGoogle Scholar
  9. 9.
    H.E. Ganther, Bioorg. Med. Chem. 9, 1459 (2001)CrossRefGoogle Scholar
  10. 10.
    Y. Xu, E.T. Kool, J. Am. Chem. Soc. 122, 9040 (2000)CrossRefGoogle Scholar
  11. 11.
    G. Mugesh, W.W. Du Mont, H. Sies, Chem. Rev. 101, 2125 (2001)CrossRefGoogle Scholar
  12. 12.
    R.F. Burk, Selenium in Biology and Human Health (Springer Verlag, New York, 1994)CrossRefGoogle Scholar
  13. 13.
    A. Wengel, Selenium in Biology and Medicine (Springer Verlag, Berlin, 1989)Google Scholar
  14. 14.
    T. Wirth, Topics in Current Chemistry: Organoselenium Chemistry, Modern Development in Organic Synthesis, vol 208 (Springer Verlag, Berlin, 2000)Google Scholar
  15. 15.
    D.L. Hatfield, Selenium. Its Molecular Biology and Role in Human Health (Kluwer Academic Publishers, Boston, 2001)Google Scholar
  16. 16.
    K. El-Bayoumy, R. Sinha, Mutat. Res. 551, 181 (2004)CrossRefGoogle Scholar
  17. 17.
    D.B. Vickerman, J.T. Trumble, G.N. George, I.J. Pickering, H. Nichol, Environ. Sci. Technol. 38, 3581 (2004)CrossRefGoogle Scholar
  18. 18.
    C. Ip, M. Birringer, E. Block, M. Kotrebai, J.F. Tyson, P.C. Uden, D.J. Lisk, J. Agric. Food Chem. 48, 2062 (2000)CrossRefGoogle Scholar
  19. 19.
    J. Lintschinger, N. Fuchs, J. Moser, D. Kuehnelt, W. Goessler, J. Agric. Food Chem. 48, 5362 (2000)CrossRefGoogle Scholar
  20. 20.
    V. Poggi, A. Arcioni, P. Filippini, P.G. Pifferi, J. Agric. Food Chem. 48, 4749 (2000)CrossRefGoogle Scholar
  21. 21.
    A.R. Katritzky, C.W. Rees, E.F.V. Scriven, in Compr. Heterocycl. Chem. II. 1,2-Thiazines and Their Benzo Derivatives, vol 6 (Pergamon Press, Amsterdam, 1996), p. 349Google Scholar
  22. 22.
    I.B. Douglas, Acylselenoureas. J. Am. Chem. Soc. 59, 740 (1937)CrossRefGoogle Scholar
  23. 23.
    H. Heimgartner, Y. Zhou, P.K. Atanassov, G.L. Sommen, Phosphorus. Sulfur. Silicon. Relat. Elem. 183, 840 (2008)CrossRefGoogle Scholar
  24. 24.
    I. Yavari, S. Mosaferi, Chem. Mon. 148, 963 (2017)CrossRefGoogle Scholar
  25. 25.
    I. Yavari, S. Mosaferi, S. Skoulika, Synlett 27, 2494 (2016)CrossRefGoogle Scholar
  26. 26.
    M. Koketsu, H. Ishihara, W. Wu, K. Murakami, I. Saiki, Eur. J. Pharm. Sci. 9, 157 (1999)CrossRefGoogle Scholar
  27. 27.
    W. Wu, K. Murakami, M. Koketsu, Y. Yamada, I. Saiki, Anticancer. Res. 19, 5375 (1999)Google Scholar
  28. 28.
    M. Koketsu, H. Ishihara, M. Hatsu, Res. Commun. Mol. Path. Pharm. 101, 179 (1998)Google Scholar
  29. 29.
    S.I. Cho, M. Koketsu, H. Ishihara, M. Matsushita, A.C. Nairn, H. Fukazawa, Y. Uehara, Biochim. Biophys. Acta 1475, 207 (2000)CrossRefGoogle Scholar
  30. 30.
    M. Sainsbury, Selenazines and Benzoselenazines, Rodd’s Chemistry of Carbon Compounds, 2nd edn., vol 4 (Elsevier, Amsterdam, 1998), p. 609Google Scholar
  31. 31.
    M. Sainsbury, in Compr. Heterocycl. Chem. II, ed. by A.R. Katritzky, C.W. Rees, E.F.V. Scriven. Six-Membered Rings with Two or More Heteroatoms With at Least One Selenium or Tellurium, vol 6 (Pergamon Press, Oxford, 1996), p. 987Google Scholar
  32. 32.
    K. Godula, D. Sames, Science 312, 67 (2006)CrossRefGoogle Scholar
  33. 33.
    D. Alberico, M.E. Scott, M. Lautens, Chem. Rev. 107, 174 (2007)CrossRefGoogle Scholar
  34. 34.
    T.G. Back, Organoselenium Chemistry, A Practical Approach (Oxford University Press, Oxford, 1999)Google Scholar
  35. 35.
    F. Kakiuchi, N. Chatani, Adv. Synth. Catal. 345, 1077 (2003)CrossRefGoogle Scholar
  36. 36.
    V. Ritleng, C. Sirlin, M. Pfeffer, Chem. Rev. 102, 1731 (2002)CrossRefGoogle Scholar
  37. 37.
    D. Ma, Q. Cai, Acc.Chem. Res. 41, 1450 (2008)CrossRefGoogle Scholar
  38. 38.
    F. Yi, S. Zhang, L. Zhang, W. Yi, R. Yu, Asian J. Org. Chem. 6, 1808 (2017)CrossRefGoogle Scholar
  39. 39.
    V. Nenajdenko, Isocyanide Chemistry: Applications in Synthesis and Material Science (Wiley-VCH, Weinheim, 2012)CrossRefGoogle Scholar
  40. 40.
    A. Shaabani, A. Maleki, A.H. Rezayan, A. Sarvary, Mol. Divers. 15, 41 (2011)CrossRefGoogle Scholar
  41. 41.
    B. Song, B. Xu, Chem. Soc. Rev. 46, 1103 (2017)CrossRefGoogle Scholar
  42. 42.
    M. Nematpour, E. Rezaee, S.A. Tabatabai, M. Jahani, Synlett 28, 1441 (2017)CrossRefGoogle Scholar
  43. 43.
    M. Nematpour, E. Rezaee, M. Jahani, S.A. Tabatabai, Tetrahedron Lett. 59, 2054 (2018)CrossRefGoogle Scholar
  44. 44.
    D. Yang, B. An, W. Wei, L. Tian, B. Huang, H. Wang, ACS Comb. Sci. 17, 113 (2015)CrossRefGoogle Scholar

Copyright information

© Iranian Chemical Society 2018

Authors and Affiliations

  • Manijeh Nematpour
    • 1
  • Elham Rezaee
    • 1
  • Mehdi Jahani
    • 2
  • Sayyed Abbas Tabatabai
    • 1
    Email author
  1. 1.Department of Pharmaceutical Chemistry, School of PharmacyShahid Beheshti University of Medical SciencesTehranIran
  2. 2.Department of ChemistrySharif University of TechnologyTehranIran

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