Exploiting Iminoquinones as Electrophilic at Nitrogen N plus Synthons for C-N Bond Construction

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.

Automated summary

New methods for C-N bond construction utilizing the N-centered electrophilic character of iminoquinones have been reported. Various nitrogen-containing heterocycles can be synthesized under different reaction conditions, demonstrating the wide application of iminoquinones in organic synthesis.