Deoxygenative Amination of Azine-N-oxides with Acyl Azides via [3 + 2] Cycloaddition
Dongeun Kim1, Prithwish Ghosh1, Na Yeon Kwon1
1School of Pharmacy , Sungkyunkwan University , Suwon 16419 , Republic of Korea.
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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