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

Tyler J. Potter, Yuantao Li, Michael D. Ward, Jonathan A. Ellman

Research output: Contribution to journalArticle

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.

Original languageEnglish (US)
Pages (from-to)4381-4388
Number of pages8
JournalEuropean Journal of Organic Chemistry
Volume2018
Issue number32
DOIs
StatePublished - Aug 31 2018

Keywords

  • Annulation
  • C–H activation
  • Nitroalkenes
  • Nitrogen heterocycles
  • Synthetic methods

ASJC Scopus subject areas

  • Physical and Theoretical Chemistry
  • Organic Chemistry

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