KHMDS mediated ring-opening/reconstruction of anthranils with arylacetonitriles: synthesis of multisubstituted 2-aminoquinoline N-oxides

Abstract

A convenient and atom-economical protocol for the construction of multisubstituted 2-aminoquinoline N-oxides using readily available starting materials anthranil and arylacetonitrile has been reported. The KHMDS mediated process tolerates various protecting groups of –OH, halo groups, and heterocycles. The ring-opening/reconstruction reaction with C3-aryl anthranils provided densely-arene-substituted 2-aminoquinoline N-oxides, which are otherwise difficult to synthesize. Overall, the ring-opening/reconstruction reaction involves C–O bond cleavage and C–C and C–N bond formation events.