Synthesis of Heterocyclic-fused Imidazoles by Pyrolysis of N-Heterocyclic Isoxazol-5(2H)-ones

Steven-Alan Abel, Matthew Eglinton, James Howard, Dylan Hunt, Rolf Prager, Jason Smith

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    Abstract

    The synthesis of heterocyclic-fused imidazoles was achieved by flash vacuum pyrolysis (FVP) of N-heterocyclic isoxazol-5(2H)-ones via an iminocarbene intermediate. Unlike iminocarbenes generated from triazoles, no structural rearrangements were observed during the current synthesis method. We also demonstrated that less volatile isoxazol-5(2H)-one derivatives yield the corresponding imidazoles by condensed phase pyrolysis.

    Original languageEnglish
    Pages (from-to)1228-1233
    Number of pages6
    JournalAustralian Journal of Chemistry
    Volume67
    Issue number8-9
    DOIs
    Publication statusPublished - 2014

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  • Cite this

    Abel, S-A., Eglinton, M., Howard, J., Hunt, D., Prager, R., & Smith, J. (2014). Synthesis of Heterocyclic-fused Imidazoles by Pyrolysis of N-Heterocyclic Isoxazol-5(2H)-ones. Australian Journal of Chemistry, 67(8-9), 1228-1233. https://doi.org/10.1071/CH14119