Redox‐Neutral Vicarious‐Type Nucleophilic Amination of Heterocyclic N‐Oxides with Organic Azides

Site‐selective amination of N ‐heterocycles is an interesting topic in organic synthesis and drug discovery. We herein present a method for the vicarious‐type nucleophilic amination of azine N ‐oxides and cyclic iminoamides using iminyl anions, readily generated from organic azides under basic conditions. The plausible reaction mechanism involving nucleophilic aromatic substitution by iminyl anions is elucidated by a series of mechanistic investigations.