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The reactivity of isocyanides with pentafluoropyridine

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Abstract

Reactivity of some isocyanides with pentafluoropyridine under basic conditions in dry dimethyl sulfoxide was investigated. The reaction of pentafluoropyridine with toluenesulfonylmethyl isocyanide (TosMIC) was less selective, but the reactions of other isocyanides with pentafluoropyridine gave the desired 2,3,5,6-tetrafluoro-N-substituted isonicotinamide. The structures of all the compounds were confirmed by IR, 1H NMR, 19F NMR, and 13C NMR spectroscopy, X-ray crystallography as well as elemental analysis.

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Acknowledgements

The authors wish to thank Vali-e-Asr University of Rafsanjan for partially funding this work.

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Authors and Affiliations

  1. Department of Chemistry, Faculty of Science, Vali-e-Asr University, Rafsanjan, 77176, Islamic Republic of Iran

    Motahereh Irani, Reza Ranjbar-Karimi, Alireza Poorfreidoni & Hossein Mehrabi

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  1. Motahereh Irani
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  2. Reza Ranjbar-Karimi
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  3. Alireza Poorfreidoni
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  4. Hossein Mehrabi
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Correspondence to Reza Ranjbar-Karimi.

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Irani, M., Ranjbar-Karimi, R., Poorfreidoni, A. et al. The reactivity of isocyanides with pentafluoropyridine. Monatsh Chem 152, 1369–1375 (2021). https://doi.org/10.1007/s00706-021-02856-x

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  • DOI: https://doi.org/10.1007/s00706-021-02856-x

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