Tf 2 NH-catalyzed formal [3 + 2] cycloaddition of oxadiazolones with ynamides: a simple access to aminoimidazoles

Oxadiazolones are first employed as the three-atom coupling partners in the Tf NH-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...

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Veröffentlicht in:Organic & biomolecular chemistry 2017-04, Vol.15 (16), p.3413-3417
Hauptverfasser: Zhao, Yingying, Hu, Yancheng, Li, Xincheng, Wan, Boshun
Format: Artikel
Sprache:eng
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Zusammenfassung:Oxadiazolones are first employed as the three-atom coupling partners in the Tf NH-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.
ISSN:1477-0520
1477-0539
DOI:10.1039/C7OB00701A