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

European J Org Chem. 2018 Aug 31;2018(32):4381-4388. doi: 10.1002/ejoc.201800745. Epub 2018 Jun 11.

Abstract

The Rh(III)-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 nitrodihydroisocoumarin. 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.

Keywords: Annulation; C-H Activation; Nitroalkenes; Nitrogen heterocycles; Synthetic methods.