RhIII-Catalyzed Synthesis of Isoquinolones and 2-Pyridones by Annulation of N-Methoxyamides and Nitroalkenes

Abstract

The RhIII-catalyzed synthesis of 4-substituted isoquinolones and 2-pyridones by the annulation of N-methoxyamides and nitroalkenes has been developed. Both aliphatic and aromatic nitroalkenes were effective inputs. Annulations also proceeded for aromatic, alkenyl, and heteroaromatic C–H bond starting materials. Moreover, benzoic acid provided a novel nitro-dihydroisocoumarin. The structure and relative stereochemistry of this compound, which is an oil at room temperature, was determined unambiguously by single-crystal X-ray diffraction of its inclusion complex with a hydrogen-bonded host framework.