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Solvent-free, one-pot synthesis of pentasubstituted cyclopropanes in the presence of BrCN and EtONa by milling

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Abstract

A solvent-free, one-pot process for the preparation of pentasubstituted 3-arylcyclopropane-1,1,2,2-tetracarbonitriles in the presence of solid sodium ethoxide by milling was achieved. The one-pot reaction of aromatic aldehydes and dialdehydes with malononitrile, cyanogen bromide, and solid sodium ethoxide afforded pentasubstituted cyclopropanes in excellent yield under solvent-free conditions. The structures were characterized and confirmed by IR, 1H NMR, 13C NMR spectroscopy, and mass spectrometry. Its advantages are easy workup, mild reaction conditions, and excellent yields.

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Acknowledgments

We gratefully acknowledge financial support by the Research Council of Urmia University.

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Authors and Affiliations

  1. Department of Chemistry, Faculty of Science, Urmia University, 57159, Urmia, Iran

    Nader Noroozi Pesyan & Mohammad Rezaee

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  1. Nader Noroozi Pesyan
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  2. Mohammad Rezaee
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Correspondence to Nader Noroozi Pesyan.

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Noroozi Pesyan, N., Rezaee, M. Solvent-free, one-pot synthesis of pentasubstituted cyclopropanes in the presence of BrCN and EtONa by milling. Monatsh Chem 145, 1165–1171 (2014). https://doi.org/10.1007/s00706-014-1180-2

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  • DOI: https://doi.org/10.1007/s00706-014-1180-2

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