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Synthesis of 4-aminoquinolines by aerobic oxidative palladium-catalyzed double C–H activation and isocyanide insertion

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Chemistry of Heterocyclic Compounds Aims and scope

An unprecedented aerobic oxidative Pd-catalyzed imidoylative coupling of two C–H fragments furnishing medicinally valuable 4-aminoquinolines is reported. Optimization studies are described and several analogs were successfully prepared.

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Notes

  1. T. Vlaar, B. U. W. Maes, E. Ruijter, R. V. A. Orru, Angew. Chem., Int. Ed., in press (DOI: 10.1002/anie.201300942); S. Lang, Chem. Soc. Rev., in press (DOI: 10.1039/C3CS60022J); G. Qiu, Q. Ding, J. Wu, Chem. Soc. Rev., in press (DOI: 10.1039/C3CS35507A).

  2. T. Vlaar, B. U. W. Maes, E. Ruijter, R. V. A. Orru, Angew. Chem., Int. Ed., in press (DOI: 10.1002/anie.201300942).

References

  1. I. Ugi, Isonitrile Chemistry, Academic Press, New York (1971).

    Google Scholar 

  2. A. Dömling and I. Ugi, Angew. Chem., Int. Ed., 39, 3168 (2000).

  3. A. Dömling, Chem. Rev., 106, 17 (2006)

    Article  Google Scholar 

  4. A. V. Lygin and A. de Meijere, Angew. Chem., Int. Ed., 49, 9094 (2010).

    Article  CAS  Google Scholar 

  5. A. V. Gulevich, A. G. Zhdanko, R. V. A. Orru, and V. G. Nenajdenko, Chem. Rev., 110, 5235 (2010).

    Article  CAS  Google Scholar 

  6. V. G. Nenajdenko, Isocyanide Chemistry, Wiley-VCH, Weinheim (2012).

    Google Scholar 

  7. C. G. Saluste, R. J. Whitby, and M. Furber, Angew. Chem., Int. Ed., 39, 4156 (2000).

    Article  CAS  Google Scholar 

  8. H. Jiang, B. Liu, Y. Li, A. Wang, and H. Huang, Org. Lett., 13, 1028 (2011).

    Article  CAS  Google Scholar 

  9. F. Zhou, K. Ding, and Q. Cai, Chem.-Eur. J., 17, 12268 (2011).

    Article  CAS  Google Scholar 

  10. P. J. Boissarie, Z. E. Hamilton, S. Lang, J. A. Murphy, and C. J. Suckling, Org. Lett., 13, 6256 (2011).

    Article  CAS  Google Scholar 

  11. G. van Baelen, S. Kuijer, L. Rýček, S. Sergeyev, E. Janssen, F. J. J. de Kanter, B. U. W. Maes, E. Ruijter, and R. V. A. Orru, Chem.-Eur. J., 17, 15039 (2011).

    Article  Google Scholar 

  12. G. Qiu, G. Liu, S. Pu, and J. Wu, Chem. Commun., 48, 2903 (2012).

    Article  CAS  Google Scholar 

  13. Y. Li, J. Zhao, H. Chen, B. Liu, and H. Jiang, Chem. Commun., 48, 3545 (2012).

    Article  CAS  Google Scholar 

  14. V. Tyagi, S. Khan, A. Giri, H. M. Gauniyal, B. Sridhar, and P. M. S. Chauhan, Org. Lett., 14, 3126 (2012).

    Article  CAS  Google Scholar 

  15. B. Liu, Y. Li, H. Jiang, M. Yin, and H. Huang, Adv. Synth. Catal., 354, 2288 (2012).

    Article  CAS  Google Scholar 

  16. T. Vlaar, E. Ruijter, A. Znabet, E. Janssen, F. J. J. de Kanter, B. U. W. Maes, and R. V. A. Orru, Org. Lett., 13, 6496 (2011).

    Article  CAS  Google Scholar 

  17. B. Liu, Y. Li, M. Yin, W. Wu, and H. Jiang, Chem. Commun., 48, 11446 (2012).

    Article  CAS  Google Scholar 

  18. X.-D. Fei, Z.-Y. Ge, T. Tang, Y.-M. Zhu, and S.-J. Ji, J. Org. Chem., 77, 10321 (2012).

    Article  CAS  Google Scholar 

  19. T. Vlaar, R. C. Cioc, P. Mampuys, B. U. W. Maes, R. V. A. Orru, and E. Ruijter, Angew. Chem., Int. Ed., 51, 13058 (2012).

    Article  CAS  Google Scholar 

  20. L. Ackermann, R. Vicente, and A. R. Kapdi, Angew. Chem., Int. Ed., 48, 9792 (2009).

    Article  CAS  Google Scholar 

  21. X. Chen, K. M. Engle, D.-H. Wang, and J.-Q. Yu, Angew. Chem., Int. Ed., 48, 5094 (2009).

    Article  CAS  Google Scholar 

  22. J. A. Ashenhurst, Chem. Soc. Rev., 39, 540 (2010).

    Article  CAS  Google Scholar 

  23. T. W. Lyons and M. S. Sanford, Chem. Rev., 110, 1147 (2010).

    Article  CAS  Google Scholar 

  24. Y. Wang, H. Wang, and J. Peng, Q. Zhu, Org. Lett., 13, 4604 (2011).

    Article  CAS  Google Scholar 

  25. Y. Wang and Q. Zhu, Adv. Synth. Catal., 354, 1902 (2012).

    Article  CAS  Google Scholar 

  26. D. P. Curran and W. Du, Org. Lett., 4, 3215 (2002).

    Article  CAS  Google Scholar 

  27. M. Tobisu, S. Imoto, S. Ito, and N. Chatani, J. Org. Chem., 75, 4835 (2010).

    Article  CAS  Google Scholar 

  28. T. Nanjo, C. Tsukano, and Y. Takemoto, Org. Lett., 14, 4270 (2012).

    Article  CAS  Google Scholar 

  29. T. Vlaar, E. Ruijter and R. V. A. Orru, Adv. Synth. Catal., 353, 809 (2011).

    Article  CAS  Google Scholar 

  30. S. Würtz, S. Rakshit, J. J. Neumann, T. Dröge, and F. Glorius, Angew. Chem., Int. Ed., 47, 7230 (2008).

    Article  Google Scholar 

  31. J. J. Neumann, S. Rakshit, T. Dröge, S. Würtz, and F. Glorius, Chem.-Eur. J., 17, 7298 (2011).

    Article  CAS  Google Scholar 

  32. Y. Wei, I. Deb, and N. Yoshikai, J. Am. Chem. Soc., 134, 9098 (2012).

    Article  CAS  Google Scholar 

  33. N. Mršić, A. J. Minnaard, B. L. Feringa, and J. G. de Vries, J. Am. Chem. Soc., 131, 8358 (2009).

    Article  Google Scholar 

  34. C. Moessner and C. Bolm, Angew. Chem., Int. Ed., 44, 7564 (2005).

    Article  CAS  Google Scholar 

  35. T. Imamoto, N. Iwadate, and K. Yoshida, Org. Lett., 8, 2289 (2006).

    Article  CAS  Google Scholar 

  36. K. Kutlescha, G. T. Venkanna, and R. Kempe, Chem. Commun., 47, 4183 (2011).

    Article  CAS  Google Scholar 

  37. A. Leyva and A. Corma, Adv. Synth. Catal., 351, 2876 (2009).

    Article  CAS  Google Scholar 

  38. A. V. Malkov, S. Stončius, K. Vranková, M. Arndt, and P. Kočovský, Chem.-Eur. J., 14, 8082 (2008).

    Article  CAS  Google Scholar 

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Authors and Affiliations

  1. Department of Chemistry & Pharmaceutical Sciences and Amsterdam Institute for Molecules, Medicines and Systems (AIMMS), VU University Amsterdam, 1083 De Boelelaan, 1081 HV, Amsterdam, The Netherlands

    T. Vlaar, E. Ruijter & R. V. A. Orru

  2. Organic Synthesis, Department of Chemistry, University of Antwerp, 171 Groenenborgerlaan, 2020, Antwerp, Belgium

    B. U. W. Maes

Authors
  1. T. Vlaar
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  2. B. U. W. Maes
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  3. E. Ruijter
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  4. R. V. A. Orru
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Corresponding author

Correspondence to R. V. A. Orru.

Additional information

Published in Khimiya Geterotsiklicheskikh Soedinenii, No. 6, pp. 966-972, June, 2013.

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Vlaar, T., Maes, B.U.W., Ruijter, E. et al. Synthesis of 4-aminoquinolines by aerobic oxidative palladium-catalyzed double C–H activation and isocyanide insertion. Chem Heterocycl Comp 49, 902–908 (2013). https://doi.org/10.1007/s10593-013-1324-z

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  • DOI: https://doi.org/10.1007/s10593-013-1324-z

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