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Participation of ethyl 3-formylindole-2-carboxylate with the Ugi four-component condensation reaction

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Abstract

Multicomponent condensation of ethyl 3-formylindole 2-carboxylate, amines, isocyanide and (S)-N-boc-alanine or (S)-N-boc-serine is described. This Ugi four-component condensation (Ugi-4CC) reaction yielded a series of novel dipeptides containing an indolyl moiety. These compounds exhibit potential biological activity.

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References

  1. J.A. Joule, In Science of Synthesis; E. J. Thomas, Ed.; Georg Thieme Verlag: Stuttgart, New York, 2000; Vol. 10, pp. 361–652

  2. R.J. Sundberg, Indoles (Academic Press, London, 1996)

    Google Scholar 

  3. G.R. Humphrey, J.T. Kuethe, Chem. Rev. 106, 2875 (2006)

    Article  CAS  Google Scholar 

  4. S. Cacchi, G. Fabrizi, Chem. Rev. 105, 2873 (2005)

    Article  CAS  Google Scholar 

  5. M. Shiri, M.A. Zolfigol, H.G. Kruger, Z. Tanbakouchian, Chem. Rev. 110, 2550 (2010)

    Article  Google Scholar 

  6. A. Domling, I. Ugi, Angew. Chem. Int. Ed. 39, 3168 (2000)

    Article  CAS  Google Scholar 

  7. A. Domling, Chem. Rev. 106, 17 (2006)

    Article  Google Scholar 

  8. J. Zhu, H. Bienaym, Multicomponent Reactions. Wiley-VCH: Weinheim, Germany, 2005

  9. M. Shiri, Chem. Rev. 112, 3508 (2012)

    Article  CAS  Google Scholar 

  10. B. Beck, S. Hess, A. Domling, Bioorg. Med. Chem. Lett. 10, 1701 (2000)

    Article  CAS  Google Scholar 

  11. M. Waki, J. Meienhofer, J. Am. Chem. Soc. 98, 6075 (1977)

    Article  Google Scholar 

  12. M. Thormann, M. Almstetter, US2007/0060624(A1)

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Acknowledgments

We thank Alzahra University and Bu-Ali Sina University and also National Elites Fundation (Iran) for financial support to our research group.

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Authors and Affiliations

  1. Department of Chemistry, Faculty of Science, Alzahra University, Vanak, 1993893973, Tehran, Iran

    Morteza Shiri

  2. Faculty of Chemistry, Bu-Ali Sina University, 6517838683, Hamedan, Iran

    Mohammad Ali Zolfigol, Ardeshir Khazaei & Toktam Faal-Rastegar

  3. Catalysis and Peptide Research Unit, School of Health Sciences, University of KwaZulu-Natal, Durban, 4001, South Africa

    Hendrik G. Kruger

Authors
  1. Morteza Shiri
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  2. Mohammad Ali Zolfigol
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  3. Ardeshir Khazaei
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  4. Toktam Faal-Rastegar
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  5. Hendrik G. Kruger
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Corresponding authors

Correspondence to Morteza Shiri or Mohammad Ali Zolfigol.

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Shiri, M., Zolfigol, M.A., Khazaei, A. et al. Participation of ethyl 3-formylindole-2-carboxylate with the Ugi four-component condensation reaction. J IRAN CHEM SOC 11, 85–90 (2014). https://doi.org/10.1007/s13738-013-0278-5

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  • DOI: https://doi.org/10.1007/s13738-013-0278-5

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