Synthesis of carbamoyl azides via the Lossen rearrangement utilizing diphenyl phosphorazidate

[Display omitted] A novel method was developed for the synthesis of carbamoyl azides from hydroxamic acids via the Lossen rearrangement using diphenyl phosphorazidate, which acts as both the activator and azide source to produce the azides via an isocyanate intermediate. Using this method, various h...

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Veröffentlicht in:Tetrahedron letters 2022-04, Vol.95, p.153727, Article 153727
Hauptverfasser: Ishihara, Kotaro, Shioiri, Takayuki, Matsugi, Masato
Format: Artikel
Sprache:eng
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Zusammenfassung:[Display omitted] A novel method was developed for the synthesis of carbamoyl azides from hydroxamic acids via the Lossen rearrangement using diphenyl phosphorazidate, which acts as both the activator and azide source to produce the azides via an isocyanate intermediate. Using this method, various hydroxamic acids were converted into the corresponding carbamoyl azides, enabling their preparation without the use of highly explosive reagents.
ISSN:0040-4039
1873-3581
DOI:10.1016/j.tetlet.2022.153727