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Rh III ‐Catalyzed Synthesis of Isoquinolones and 2‐Pyridones by Annulation of N ‐Methoxyamides and Nitroalkenes
Author(s) -
Potter Tyler J.,
Li Yuantao,
Ward Michael D.,
Ellman Jonathan A.
Publication year - 2018
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201800745
Subject(s) - annulation , chemistry , catalysis , crystal structure , nitro , medicinal chemistry , benzoic acid , hydrogen bond , stereochemistry , single crystal , organic chemistry , molecule , crystallography , alkyl
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 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.