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

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

Author information

1
Department of Chemistry, Yale University, New Haven, Connecticut 06520, United States.
2
Department of Chemistry and Molecular Design Institute, New York University, 100 Washington Square East, Room 1001, New York City, NY 10009, United States.

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

PMID:
30220876
PMCID:
PMC6136657
[Available on 2019-08-31]
DOI:
10.1002/ejoc.201800745

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