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Synthesis and structure of dialkyl (Z)-3-amino-2-cyano-4-diazopent-2-enedioates

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Abstract

Diazo-transfer reaction of tosyl azide and alkyl 2-cyanoacetates in the presence of pyridine at 0 °C gives the corresponding alkyl 2-cyano-2-diazoacetates. This material readily undergoes nucleophilic attack by pyridinium 1-cyano-2-alkoxy-2-oxoethan-1-ide to form dialkyl (Z)-3-amino-2-cyano-4-diazopent-2-enedioates. The X-ray structure of a typical product is reported, as well as DFT computational studies that illuminate the structural features of these stable diazo compounds.

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Acknowledgements

We would like to thank the Research Council of Tarbiat Modares University for supporting this work.

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Authors and Affiliations

  1. Department of Chemistry, Tarbiat Modares University, PO Box 14115-175, Tehran, Iran

    Issa Yavari, Ramin Mohsenzadeh & Jasmine Kayanian

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  1. Issa Yavari
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  2. Ramin Mohsenzadeh
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  3. Jasmine Kayanian
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Correspondence to Issa Yavari.

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Yavari, I., Mohsenzadeh, R. & Kayanian, J. Synthesis and structure of dialkyl (Z)-3-amino-2-cyano-4-diazopent-2-enedioates. Monatsh Chem 151, 1829–1834 (2020). https://doi.org/10.1007/s00706-020-02712-4

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  • DOI: https://doi.org/10.1007/s00706-020-02712-4

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