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New synthetic protocol for stereoselective synthesis of diethyl 1,2-dicyano-3-alkyl-(aryl)cyclopropane-1,2-dicarboxylate

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Abstract

A new, fast and straightforward method for the one-pot reaction of aromatic and aliphatic aldehydes and dialdehydes with ethyl cyanoacetate and cyanogen bromide was developed to afford stereoselectively diethyl 1,2-dicyano-3-alkyl/arylcyclopropane-1,2-dicarboxylate in excellent yields and short reaction time (about 5 s). The structures were characterized by IR, 1H NMR and 13C NMR spectroscopy. The reaction mechanism was discussed.

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Acknowledgments

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

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Authors and Affiliations

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

    Nader Noroozi Pesyan & Saeed Golizadeh

Authors
  1. Nader Noroozi Pesyan
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  2. Saeed Golizadeh
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Correspondence to Nader Noroozi Pesyan.

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13738_2015_590_MOESM1_ESM.pdf

Supplementary material 1 Full characterization data of compounds 4a′, 3a, 3c–3h, 3l and 9c″ are available. (PDF 2539 kb)

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Noroozi Pesyan, N., Golizadeh, S. New synthetic protocol for stereoselective synthesis of diethyl 1,2-dicyano-3-alkyl-(aryl)cyclopropane-1,2-dicarboxylate. J IRAN CHEM SOC 12, 1261–1273 (2015). https://doi.org/10.1007/s13738-015-0590-3

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  • DOI: https://doi.org/10.1007/s13738-015-0590-3

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