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Issue 16, 2017
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Tf2NH-catalyzed formal [3 + 2] cycloaddition of oxadiazolones with ynamides: a simple access to aminoimidazoles

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Abstract

Oxadiazolones are first employed as the three-atom coupling partners in the Tf2NH-catalyzed cycloaddition with ynamides. This formal [3 + 2] cycloaddition allows a rapid synthesis of aminoimidazoles with a broad substrate scope. The approach also features a metal-free catalytic cycloaddition process, which may find applications in the synthesis of bioactive molecules. Besides, the resulting N-methyl products can further be readily converted to free N–H aminoimidazoles.

Graphical abstract: Tf2NH-catalyzed formal [3 + 2] cycloaddition of oxadiazolones with ynamides: a simple access to aminoimidazoles

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Publication details

The article was received on 22 Mar 2017, accepted on 30 Mar 2017 and first published on 30 Mar 2017


Article type: Communication
DOI: 10.1039/C7OB00701A
Citation: Org. Biomol. Chem., 2017,15, 3413-3417
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    Tf2NH-catalyzed formal [3 + 2] cycloaddition of oxadiazolones with ynamides: a simple access to aminoimidazoles

    Y. Zhao, Y. Hu, X. Li and B. Wan, Org. Biomol. Chem., 2017, 15, 3413
    DOI: 10.1039/C7OB00701A

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