A Straightforward Synthesis of Functionalized cis-Perhydroisoquinolin-1-ones

Molecules. 2019 Feb 3;24(3):557. doi: 10.3390/molecules24030557.

Abstract

Base-catalyzed annulation reactions of 5,6-dihydro-2(1H)-pyridones with Nazarov-type reagents are reported. The effect of the solvent polarity and the concentration of the reagents is studied. The process involves two successive Michael additions and stereoselectively provides functionalized cis-perhydroisoquinolin-1-ones.

Keywords: 5,6-dihydro-2(1H)-pyridone; Michael addition; Nazarov reagents; perhydroisoquinoline; stereoselectivity.

MeSH terms

  • Catalysis
  • Chemistry Techniques, Synthetic*
  • Hydrogen Peroxide / chemistry*
  • Isoquinolines / chemical synthesis
  • Isoquinolines / chemistry*
  • Models, Molecular
  • Molecular Conformation
  • Molecular Structure

Substances

  • Isoquinolines
  • Hydrogen Peroxide
  • isoquinoline