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

초록

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.

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