Synthesis of 15N-labeled heterocycles via the cleavage of C-N bonds of anilines and glycine-15N.

A nitrogen replacement process that directly incorporates the 15N atom of glycine-15N into anilines was reported. The process involves a Csp2-N bond cleavage of anilines driven by dearomatization and a Csp3-N bond cleavage of glycine-15N driven by aromatization. A variety of 15N-labeled aromatic heterocycles can be prepared via this process.