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Base-catalyzed cyclization of Ugi-adducts to substituted indolyl based γ-lactams

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Abstract

Post-condensation cyclization of Ugi adducts from the condensation of 2-formylindole, isocyanides, amines, and 3-chloropropanoic acid was performed selectively in the presence of K2CO3 to form a series of novel substituted γ-lactams.

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References

  1. Zhu J, Bienaymé H (2005) Multicomponent reactions. Wiley-VCH, Weinheim

    Book  Google Scholar 

  2. Dömling A, Huang Y (2010) Synthesis 2859

  3. Shaabani A, Maleki A, Rezayan A, Sarvary A (2011) Mol Divers 15:41

    Article  CAS  Google Scholar 

  4. Sadjadi S, Heravi MM (2011) Tetrahedron 67:2707

    Article  CAS  Google Scholar 

  5. Ivachtchenko AV, Ivanenkov YA, Kysil VM, Krasavin MY, Ilyin AP (2010) Russ Chem Rev 79:787

    Article  CAS  Google Scholar 

  6. Shiri M (2012) Chem Rev 112:3508

    Article  CAS  Google Scholar 

  7. Dömling A, Wang W, Wang K (2012) Chem Rev 112:3083

    Article  Google Scholar 

  8. Simon C, Constantieux T, Rodriguez J (2004) Eur J Org Chem 4957

  9. Ugi I, Steinbrückner C (1961) Aminocarboxylic acid amides and derivatives. German patent DE 1103337, March 30, 1961; (1962) Chem Abstr 57:62803

  10. Ugi I, Meyr R, Fetzer U (1959) Angew Chem Int Ed 71:386

    Google Scholar 

  11. Dömling A, Ugi I (2000) Angew Chem Int Ed 39:3168

    Article  Google Scholar 

  12. Dömling A (2006) Chem Rev 106:17

    Article  Google Scholar 

  13. Borthwick AD (2012) Chem Rev 112:3641

    Article  CAS  Google Scholar 

  14. Bossio R, Fernandez Marcos C, Marcaccini S, Pepino R (1997) Tetrahedron Lett 38:2519

  15. Marcaccini S, Pepino R, Pozo MC (2001) Tetrahedron Lett 42:2727

    Article  CAS  Google Scholar 

  16. Bruttomesso AC, Eiras J, Ramírez JA, Galagovsky LR (2009) Tetrahedron Lett 50:4022

    Article  CAS  Google Scholar 

  17. Banfi L, Basso A, Guanti G, Kielland N, Repetto C, Riva R (2007) J Org Chem 72:2151

    Article  CAS  Google Scholar 

  18. Banfi L, Riva R, Basso A (2010) Synlett 23

  19. Zhang L, Zhao F, Zheng M, Zhai Y, Liu H (2013) Chem Commun 49:2894

    Article  CAS  Google Scholar 

  20. Jida M, Malaquin S, Deprez-Poulain R, Laconde G, Deprez B (2010) Tetrahedron Lett 51:5109

    Article  CAS  Google Scholar 

  21. Soleymanifard B, Heravi MM, Shiri M, Zolfigol MA, Rafiee M, Kruger HG, Naicker T, Rasekhmanesh F (2012) Tetrahedron Lett 53:3546

    Article  CAS  Google Scholar 

  22. Shiri M, Zolfigol MA, Khazaei A, Faal-Rastegar T, Kruger HG (2014) J Iran Chem Soc 11:85

    Article  CAS  Google Scholar 

  23. Eckert H (2012) Molecules 17:1074

    Article  CAS  Google Scholar 

Download references

Acknowledgments

We thank Alzahra University and Iran National Science Foundation (INSF) for financial support to our research group.

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Authors and Affiliations

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

    Morteza Shiri, Seyedeh Zeinab Mirpour-Marzoni, Zahra Bozorgpour-Savadjani & Bita Soleymanifard

  2. 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. Seyedeh Zeinab Mirpour-Marzoni
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  3. Zahra Bozorgpour-Savadjani
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  4. Bita Soleymanifard
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  5. Hendrik G. Kruger
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Correspondence to Morteza Shiri.

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Shiri, M., Mirpour-Marzoni, S.Z., Bozorgpour-Savadjani, Z. et al. Base-catalyzed cyclization of Ugi-adducts to substituted indolyl based γ-lactams. Monatsh Chem 145, 1947–1952 (2014). https://doi.org/10.1007/s00706-014-1271-0

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  • DOI: https://doi.org/10.1007/s00706-014-1271-0

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