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

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A Correction to this article was published on 26 September 2018

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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.

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Scheme 1
Scheme 2
Scheme 3
Scheme 4

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Change history

  • 26 September 2018

    The original version of this article unfortunately contained mistakes. Table 2, entry 6. The structure of the product 4f is missing.

References

  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)

    Article  CAS  PubMed  Google Scholar 

  2. R. David, Expert Opin. Investig. Drugs 7, 1063 (1998)

    Article  CAS  PubMed  Google Scholar 

  3. M. Naylor, M. Stephens, J. Nolan, B. Sutton, J. Tocher, E. Fielden, G. Adams, I. Stratford, Anticancer Drug Des. 8, 439 (1993)

    CAS  PubMed  Google Scholar 

  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)

    Article  CAS  PubMed  Google Scholar 

  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)

    Article  CAS  PubMed  Google Scholar 

  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)

    Article  CAS  Google Scholar 

  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)

    Article  CAS  PubMed  Google Scholar 

  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)

    Article  CAS  PubMed  Google Scholar 

  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)

    Article  CAS  Google Scholar 

  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)

    Article  CAS  PubMed  Google Scholar 

  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)

    Article  CAS  PubMed  Google Scholar 

  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)

    Article  CAS  PubMed  Google Scholar 

  13. J.J. Li, J. Org. Chem. 64, 8425 (1999)

    Article  CAS  PubMed  Google Scholar 

  14. D.E. Ames, M.I. Brohi, J. Chem. Soc. Perkin Trans. 1, 1384 (1980)

    Article  Google Scholar 

  15. A. Arcadi, S. Cacchi, G. Fabrizi, L.M. Parisi, Tetrahedron Lett. 45, 2431 (2004)

    Article  CAS  Google Scholar 

  16. D.M. D’Souza, T.J. Mueller, Chem. Soc. Rev. 36, 1095 (2007)

    Article  PubMed  Google Scholar 

  17. K. Sonogashira, Y. Tohda, N. Hagihara, Tetrahedron Lett. 16, 4467 (1975)

    Article  Google Scholar 

  18. R. Chinchilla, C. Najera, Chem. Rev. 107, 874 (2007)

    Article  CAS  PubMed  Google Scholar 

  19. S. Ma, E. Negishi, J. Am. Chem. Soc. 117, 6345 (1995)

    Article  CAS  Google Scholar 

  20. C. Chowdhury, G. Chaudhuri, S. Guha, A. k. Mukherjee, N.G. Kundu, J. Org. Chem. 63, 1863 (1998)

    Article  CAS  Google Scholar 

  21. B. Kundu, B. Nandi, J. Org. Chem. 66, 4563 (2001)

    Article  CAS  PubMed  Google Scholar 

  22. M.M. Heravi, S. Sadjadi, Tetrahedron 65, 7761 (2009)

    Article  CAS  Google Scholar 

  23. A. Keivanloo, M. Bakherad, A. Rahimi, S.A.N. Taheri, Tetrahedron Lett. 51, 2409 (2010)

    Article  CAS  Google Scholar 

  24. A. Keivanloo, M. Bakherad, A. Rahimi, Synthesis 2010, 1599, (2010)

  25. A. Keivanloo, M. Bakherad, M. Rahmani, A. Rahimi, Monatsh. Chem. 144, 859 (2013)

    Article  CAS  Google Scholar 

  26. A. Keivanloo, S.S. Kazemi, H. Nasr-Isfahani, A. Bamoniri, Tetrahedron 72, 6536 (2016)

    Article  CAS  Google Scholar 

  27. S.S. Kazemi, A. Keivanloo, H. Nasr-Isfahani, A. Bamoniri, RSC Adv. 6, 92663 (2016)

    Article  CAS  Google Scholar 

  28. T. Besharati-Seidani, A. Keivanloo, B. Kaboudin, T. Yokomatsu, RSC Adv. 6, 83901 (2016)

    Article  CAS  Google Scholar 

  29. A. Elangovan, Y.-H. Wang, T.-I. Ho, Org. Lett. 5, 1841 (2003)

    Article  CAS  PubMed  Google Scholar 

  30. P. Siemsen, R.C. Livingston, F. Diederich, Angew Chem. Int. Ed. 39, 2632 (2000)

    Article  CAS  Google Scholar 

  31. J. Cheng, Y. Sun, F. Wang, M. Guo, J.-H. Xu, Y. Pan, Z. Zhang, J. Org. Chem. 69, 5428 (2004)

    Article  CAS  PubMed  Google Scholar 

  32. H. Zhong, J. Wang, L. Li, R. Wang, Dalton Trans. 43, 2098, (2014)

    Article  CAS  PubMed  Google Scholar 

  33. N.E. Leadbeater, B.J. Tominack, Tetrahedron Lett. 44, 8653 (2003)

    Article  CAS  Google Scholar 

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Acknowledgements

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

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Authors and Affiliations

  1. Faculty of Chemistry, Shahrood University of Technology, Shahrood, 36199-95161, Iran

    Ali Keivanloo, Mahsa Fakharian & Amir Hossein Amin

  2. Department of Chemistry and Petroleum Faculty of Sciences, Shahid Beheshti University, Evin, Tehran, Iran

    Mohammad Reza Nabid

Authors
  1. Ali Keivanloo
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  2. Mahsa Fakharian
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  3. Mohammad Reza Nabid
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  4. Amir Hossein Amin
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Corresponding author

Correspondence to Ali Keivanloo.

Additional information

The ​original ​version ​of ​this ​article ​was ​revised: The structure of the product 4f is shown in Table 2, entry 6.

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Keivanloo, A., Fakharian, M., Nabid, M.R. et al. Novel one-pot synthesis of 1-alkyl-2-(aryloxy)methyl-1H-pyrrolo[2,3-b]quinoxalines via copper-free Sonogashira coupling reaction. J IRAN CHEM SOC 16, 151–160 (2019). https://doi.org/10.1007/s13738-018-1492-y

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