Rh(II)-Catalyzed Synthesis of N-Aryl 2-pyridone Using 2-Oxypyridine and Diazonaphthoquinone Via 1,6-Benzoyl Migratory Rearrangement.

Abstract

A Rh(II)-catalyzed simple and efficient synthesis of N-arylated 2-pyridone derivatives is described using 2-oxypyridine and diazonaphthoquinone as coupling partners. The reaction proceeds through the insertion of the nitrogen atom of the 2-oxypyridine derivative into quinoid carbene and subsequent 1,6-benzoyl migratory rearrangement. The reaction is broadened with sufficient scope and has the potential to offer axially chiral N-arylated 2-pyridone derivatives under suitable asymmetric conditions.