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Journal of the Iranian Chemical Society

, Volume 16, Issue 1, pp 151–160 | Cite as

Novel one-pot synthesis of 1-alkyl-2-(aryloxy)methyl-1H-pyrrolo[2,3-b]quinoxalines via copper-free Sonogashira coupling reaction

  • Ali KeivanlooEmail author
  • Mahsa Fakharian
  • Mohammad Reza Nabid
  • Amir Hossein Amin
Original Paper
  • 36 Downloads

Abstract

A novel, simple, and efficient protocol is described for the synthesis of 1-alkyl-2-(aryloxy)methyl-1H-pyrrolo[2,3-b]quinoxalines via the one-pot reaction of phenol or 2-naphthol derivatives, propargyl bromide, and N-alkyl-3-chloroquinoxaline-2-amines in the presence of palladium catalyst. This one-pot reaction is carried out in the absence of any copper salt at room temperature. The reaction product is dependent on the nature of the base used. The use of morpholine, as the base, affords the final cyclized product, and triethylamine only gives the coupling product.

Graphical abstract

Keywords

Sonogashira coupling Palladium-catalyzed reaction Copper-free Propargyl bromide Pyrrolo[2,3-b]quinoxalines 

Notes

Acknowledgements

We gratefully acknowledge the financial support of the Research Council of the Shahrood University of Technology.

Supplementary material

13738_2018_1492_MOESM1_ESM.docx (11.3 mb)
Supplementary material 1 (DOCX 11521 KB)

References

  1. 1.
    J. Harmenberg, A. Åkesson-Johansson, A. Gräslund, T. Malmfors, J. Bergman, B. Wahren, S. Åkerfeldt, L. Lundblad, S. Cox, Antiviral Res. 15, 193 (1991)CrossRefGoogle Scholar
  2. 2.
    R. David, Expert Opin. Investig. Drugs 7, 1063 (1998)CrossRefGoogle Scholar
  3. 3.
    M. Naylor, M. Stephens, J. Nolan, B. Sutton, J. Tocher, E. Fielden, G. Adams, I. Stratford, Anticancer Drug Des. 8, 439 (1993)Google Scholar
  4. 4.
    G. Campiani, E. Morelli, S. Gemma, V. Nacci, S. Butini, M. Hamon, E. Novellino, G. Greco, A. Cagnotto, M. Goegan, J. Med. Chem. 42, 4362 (1999)CrossRefGoogle Scholar
  5. 5.
    G. Campiani, F. Aiello, M. Fabbrini, E. Morelli, A. Ramunno, S. Armaroli, V. Nacci, A. Garofalo, G. Greco, E. Novellino, J. Med. Chem. 44, 305 (2001)CrossRefGoogle Scholar
  6. 6.
    J. Guillon, S. Moreau, E. Mouray, V. Sinou, I. Forfar, S.B. Fabre, V. Desplat, P. Millet, D. Parzy, C. Jarry, Biorg. Med. Chem. 16, 9133 (2008)CrossRefGoogle Scholar
  7. 7.
    G. Szabó, R. Kiss, D. Páyer-Lengyel, K. Vukics, J. Szikra, A. Baki, L. Molnár, J. Fischer, G.M. Keserű, Bioorg. Med. Chem. Lett. 19, 3471 (2009)CrossRefGoogle Scholar
  8. 8.
    V. Desplat, S. Moreau, A. Gay, S.B. Fabre, D. Thiolat, S. Massip, G. Macky, F. Godde, D. Mossalayi, C. Jarry, J. Enzyme Inhib. Med. Chem. 25, 204 (2010)CrossRefGoogle Scholar
  9. 9.
    B. Prasad, K.S. Kumar, P.V. Babu, K. Anusha, D. Rambabu, A. Kandale, G. Vanaja, A.M. Kalle, M. Pal, Tetrahedron Lett. 53, 6059 (2012)CrossRefGoogle Scholar
  10. 10.
    A. Nakhi, M.S. Rahman, R. Kishore, C.L.T. Meda, G.S. Deora, K.V. Parsa, M. Pal, Bioorg. Med. Chem. Lett. 22, 6433 (2012)CrossRefGoogle Scholar
  11. 11.
    J. Miyashiro, K.W. Woods, C.H. Park, X. Liu, Y. Shi, E.F. Johnson, J.J. Bouska, A.M. Olson, Y. Luo, E.H. Fry, Bioorg. Med. Chem. Lett. 19, 4050 (2009)CrossRefGoogle Scholar
  12. 12.
    V. Desplat, A. Geneste, M.-A. Begorre, S.B. Fabre, S. Brajot, S. Massip, D. Thiolat, D. Mossalayi, C. Jarry, J. Guillon, J. Enzyme Inhib. Med. Chem. 23, 648 (2008)CrossRefGoogle Scholar
  13. 13.
    J.J. Li, J. Org. Chem. 64, 8425 (1999)CrossRefGoogle Scholar
  14. 14.
    D.E. Ames, M.I. Brohi, J. Chem. Soc. Perkin Trans. 1, 1384 (1980)CrossRefGoogle Scholar
  15. 15.
    A. Arcadi, S. Cacchi, G. Fabrizi, L.M. Parisi, Tetrahedron Lett. 45, 2431 (2004)CrossRefGoogle Scholar
  16. 16.
    D.M. D’Souza, T.J. Mueller, Chem. Soc. Rev. 36, 1095 (2007)CrossRefGoogle Scholar
  17. 17.
    K. Sonogashira, Y. Tohda, N. Hagihara, Tetrahedron Lett. 16, 4467 (1975)CrossRefGoogle Scholar
  18. 18.
    R. Chinchilla, C. Najera, Chem. Rev. 107, 874 (2007)CrossRefGoogle Scholar
  19. 19.
    S. Ma, E. Negishi, J. Am. Chem. Soc. 117, 6345 (1995)CrossRefGoogle Scholar
  20. 20.
    C. Chowdhury, G. Chaudhuri, S. Guha, A. k. Mukherjee, N.G. Kundu, J. Org. Chem. 63, 1863 (1998)CrossRefGoogle Scholar
  21. 21.
    B. Kundu, B. Nandi, J. Org. Chem. 66, 4563 (2001)CrossRefGoogle Scholar
  22. 22.
    M.M. Heravi, S. Sadjadi, Tetrahedron 65, 7761 (2009)CrossRefGoogle Scholar
  23. 23.
    A. Keivanloo, M. Bakherad, A. Rahimi, S.A.N. Taheri, Tetrahedron Lett. 51, 2409 (2010)CrossRefGoogle Scholar
  24. 24.
    A. Keivanloo, M. Bakherad, A. Rahimi, Synthesis 2010, 1599, (2010)Google Scholar
  25. 25.
    A. Keivanloo, M. Bakherad, M. Rahmani, A. Rahimi, Monatsh. Chem. 144, 859 (2013)CrossRefGoogle Scholar
  26. 26.
    A. Keivanloo, S.S. Kazemi, H. Nasr-Isfahani, A. Bamoniri, Tetrahedron 72, 6536 (2016)CrossRefGoogle Scholar
  27. 27.
    S.S. Kazemi, A. Keivanloo, H. Nasr-Isfahani, A. Bamoniri, RSC Adv. 6, 92663 (2016)CrossRefGoogle Scholar
  28. 28.
    T. Besharati-Seidani, A. Keivanloo, B. Kaboudin, T. Yokomatsu, RSC Adv. 6, 83901 (2016)CrossRefGoogle Scholar
  29. 29.
    A. Elangovan, Y.-H. Wang, T.-I. Ho, Org. Lett. 5, 1841 (2003)CrossRefGoogle Scholar
  30. 30.
    P. Siemsen, R.C. Livingston, F. Diederich, Angew Chem. Int. Ed. 39, 2632 (2000)CrossRefGoogle Scholar
  31. 31.
    J. Cheng, Y. Sun, F. Wang, M. Guo, J.-H. Xu, Y. Pan, Z. Zhang, J. Org. Chem. 69, 5428 (2004)CrossRefGoogle Scholar
  32. 32.
    H. Zhong, J. Wang, L. Li, R. Wang, Dalton Trans. 43, 2098, (2014)CrossRefGoogle Scholar
  33. 33.
    N.E. Leadbeater, B.J. Tominack, Tetrahedron Lett. 44, 8653 (2003)CrossRefGoogle Scholar

Copyright information

© Iranian Chemical Society 2018
corrected publication September/2018

Authors and Affiliations

  1. 1.Faculty of ChemistryShahrood University of TechnologyShahroodIran
  2. 2.Department of Chemistry and Petroleum Faculty of SciencesShahid Beheshti UniversityTehranIran

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