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Highly selective base-catalyzed ring closing Ugi-adducts from the reaction of 2-formylindole, 2-bromoacetic acid, amines and isocyanides

Journal of the Iranian Chemical Society volume 12, pages 389–396 (2015)Cite this article

Abstract

The intermediate products of the Ugi reaction between indole-2-carboxaldehyde, 2-bromoacetic acid, amines and isocyanides were treated with Cs2CO3 in DMF to form a series of novel cyclized 1,2-dihydropyrazino[1,2-a]indol-3(4H)-ones (indole –NH cyclization) as major and piperazin-2-ones (amide –NH cyclization) as minor products.

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Scheme 1
Scheme 2

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Acknowledgments

We thank Alzahra University and Iran National Science Foundation (INSF) for financial support to our research group. We thank the Catalysis and Peptide Research Unit (http://cpru.ukzn.ac.za/Homepage.aspx) at UKZN for assistance with the NMR analysis of these compounds.

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Authors and Affiliations

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

    Morteza Shiri & Zahra Bozorgpour-Savadjani

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  1. Morteza Shiri
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  2. Zahra Bozorgpour-Savadjani
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Correspondence to Morteza Shiri.

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Shiri, M., Bozorgpour-Savadjani, Z. Highly selective base-catalyzed ring closing Ugi-adducts from the reaction of 2-formylindole, 2-bromoacetic acid, amines and isocyanides. J IRAN CHEM SOC 12, 389–396 (2015). https://doi.org/10.1007/s13738-014-0495-6

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  • DOI: https://doi.org/10.1007/s13738-014-0495-6

Keywords

  • Multicomponent condensation reactions
  • Indole
  • Base-catalyzed cyclization
  • Pyrazino[1,2-a]indolone