Exploiting Iminoquinones as Electrophilic at Nitrogen "N+" Synthons for C-N Bond Construction
Luis M Mori-Quiroz1, Chelsea G Comadoll1, Jonathan E Super1
1Department of Chemistry, The University of Kansas, 1140 Gray-Little Hall, 1567 Irving Hill Road, Lawrence, Kansas 66045, United States.
Abstract:
New methods for C-N bond construction exploiting the N-centered electrophilic character of iminoquinones are reported. Iminoquinones, generated in situ via the condensation of o-vinylanilines with benzoquinones, undergo acid-catalyzed cyclization to afford N-arylindoles in excellent yields. Under similar reaction conditions, homoallylic amines react analogously to afford N-arylpyrroles. Additionally, organometallic nucleophiles are shown to add to the nitrogen atom of N-alkyliminoquinones to provide amine products. Finally, iminoquinones are shown to be competent electrophiles for copper-catalyzed hydroamination.
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