Novel Diels-Alder reaction of 4-nitro-1(2H)-isoquinolones

Chem Pharm Bull (Tokyo). 2006 Feb;54(2):209-12. doi: 10.1248/cpb.54.209.

Abstract

A novel Diels-Alder (DA) reaction with 4-nitro-1(2H)-isoquinolones acting as the dienophile afforded 5(6H)-phenanthridone derivatives. The DA reaction of 4-nitro-1(2H)-isoquinolone with 1-methoxy-1,3-butadiene gave biologically active 5(6H)-phenanthridone possessing in a high yield. Regioselectivity of 4-nitro-1(2H)-isoquinolones with 1-methoxy-3-silyloxy-1,3-butadiene was calculated using molecular orbital (MO) calculations.

MeSH terms

  • Butadienes / chemistry
  • Chemical Phenomena
  • Chemistry, Physical
  • Chromatography, Thin Layer
  • Indicators and Reagents
  • Isoquinolines / chemical synthesis*
  • Magnetic Resonance Spectroscopy
  • Models, Molecular
  • Molecular Conformation
  • Nitro Compounds / chemical synthesis*
  • Spectroscopy, Fourier Transform Infrared

Substances

  • Butadienes
  • Indicators and Reagents
  • Isoquinolines
  • Nitro Compounds
  • 2-methoxy-1,3-butadiene