Uncatalyzed, on water oxygenative cleavage of inert C–N bond with concomitant 8,7-amino shift in 8-aminoquinoline derivatives

Abstract

Oxygenative cleavage of an inert C_Ar–NH₂ bond with concomitant 1,2 amine migration in 8-aminoquinoline derivatives is reported in water at room temperature. The reaction is highly atom- and step-economical as both C- and N-containing fragments of the C–N bond cleavage are incorporated into the target molecule and is effected without the need for N-oxide. The reaction is scalable to gram level, and the products are useful as electrophilic partners for coupling reactions, ligands in catalysis and bioactive compounds.