Deoxygenative Amination of Azine-N-oxides with Acyl Azides via [3 + 2] Cycloaddition.
J Org Chem
; 85(4): 2476-2485, 2020 02 21.
Article
em En
| MEDLINE
| ID: mdl-31904240
ABSTRACT
A transition-metal-free deoxygenative C-H amination reaction of azine-N-oxides with acyl azides is described. The initial formation of an isocyanate from the starting acyl azide via a Curtius rearrangement can trigger a [3 + 2] dipolar cycloaddition of polar N-oxide fragments to generate the aminated azine derivative. The applicability of this method is highlighted by the late-stage and sequential amination reactions of complex bioactive compounds, including quinidine and fasudil. Moreover, the direct transformation of aminated azines into various bioactive N-heterocycles illustrates the significance of this newly developed protocol.
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Base de dados:
MEDLINE
Idioma:
En
Ano de publicação:
2020
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Article