3-Nitroindoles Serving as N -Centered Nucleophiles for Aza-1,6-Michael Addition to para -Quinone Methides.

An unprecedented N -alkylation of 3-nitroindoles with para -quinone methides was developed for the first time. Using potassium carbonate as the base, a wide range of structurally diverse N -diarylmethylindole derivatives were obtained with moderated to good yields via the protection group migration/ aza -1,6-Michael addition sequences. The reaction process was also demonstrated by control experiments. Different from the previous advances where 3-nitrodoles served as electrophiles trapping by various nucleophiles, the reaction herein is featured that 3-nitrodoles is defined with latent N -centered nucleophiles to react with ortho -hydrophenyl p -QMs for construction of various N -diarylmethylindoles.