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Efficient copper(I)-catalyzed, microwave-assisted, one-pot synthesis of 3,4-diaryl isoquinolines

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Abstract

An efficient copper-catalyzed, microwave-assisted, one-pot reaction has been developed for synthesis of 3,4-diaryl isoquinolines. The reaction was performed in two steps via a CuI/2,2′-biimidazole-catalyzed tandem process from N-tert-butyl-o-iodobenzaldimine and a terminal aryl alkyne, followed by addition of an aryl iodide. A variety of 3,4-diaryl isoquinolines have been obtained in moderate to good yields.

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References

  1. R.S. Gupta, V.P. Dixit, M.P. Dobhal, Fitoterapia 61, 67 (1990)

    Google Scholar 

  2. M. Zheng, Y. Yang, M. Zhao, X. Zhang, J. Wu, G. Chen, L. Peng, Y. Wang, S. Peng, Eur. J. Med. Chem. 46, 1672 (2011)

    Article  CAS  Google Scholar 

  3. J.F. Miller, K.S. Gudmundsson, L.D. Richardson, S. Jenkinson, A. Spaltenstein, M. Thomson, P. Wheelan, Bioorg. Med. Chem. Lett. 20, 3026 (2010)

    Article  CAS  Google Scholar 

  4. M. He, D. Yuan, W. Lin, R. Pang, X. Yu, M. Yang, Bioorg. Med. Chem. Lett. 15, 3978 (2005)

    Article  CAS  Google Scholar 

  5. X. Zhang, W. Ye, S. Zhao, C.T. Che, Phytochemistry 65, 929 (2004)

    Article  CAS  Google Scholar 

  6. D.S. Bae, Y.H. Kim, C.H. Pan, C.W. Nho, J. Samdan, J. Yansan, J.K. Lee, BMB. Rep. 45, 108 (2012)

    Article  CAS  Google Scholar 

  7. F. Yang, J. Zhang, Y. Wu, Tetrahedron 67, 2969 (2011)

    Article  CAS  Google Scholar 

  8. K.R. Roesch, H.M. Zhang, R.C. Larock, J. Org. Chem. 66, 8042 (2001)

    Article  CAS  Google Scholar 

  9. T. Konno, J. Chae, T. Miyabe, T. Ishihara, J. Org. Chem. 70, 10172 (2005)

    Article  CAS  Google Scholar 

  10. G. Dai, R.C. Larock, Org. Lett. 3, 4035 (2001)

    Article  CAS  Google Scholar 

  11. R.P. Korivi, C.H. Cheng, Org. Lett. 7, 5179 (2005)

    Article  CAS  Google Scholar 

  12. C.C. Liu, R.P. Korivi, C.H. Cheng, Chem. Eur. J. 14, 9503 (2008)

    Article  CAS  Google Scholar 

  13. X. Yu, J. Wu, J. Comb. Chem. 11, 895 (2009)

    Article  CAS  Google Scholar 

  14. C.O. Kappe, Chem. Soc. Rev. 37, 1127 (2008)

    Article  CAS  Google Scholar 

  15. V. Polshettiwar, R.S. Varma, Chem. Soc. Rev. 37, 1546 (2008)

    Article  CAS  Google Scholar 

  16. D. Dallinger, C.O. Kappe, Chem. Rev. 107, 2563 (2007)

    Article  CAS  Google Scholar 

  17. Z. Hu, S.D. Li, P.Z. Hong, Arkivoc 2010, 171 (2010)

    Article  Google Scholar 

  18. Z. Hu, W. Ye, H. Zou, Y. Yu, Synth. Commun. 40, 222 (2010)

    Article  CAS  Google Scholar 

  19. Z. Hu, S.D. Li, P.Z. Hong, Z. Wu, Arkivoc 2011, 147 (2011)

    Article  Google Scholar 

Download references

Acknowledgments

This work was supported by the Program for Excellent Talents in Guangdong Ocean University (Grant No. 0912118).

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Correspondence to Zhang Hu.

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Hu, Z., Ou, LL., Li, SD. et al. Efficient copper(I)-catalyzed, microwave-assisted, one-pot synthesis of 3,4-diaryl isoquinolines. Res Chem Intermed 41, 3461–3469 (2015). https://doi.org/10.1007/s11164-013-1462-z

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  • DOI: https://doi.org/10.1007/s11164-013-1462-z

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