Acid-catalyzed photoreaction of 6-chloro-1,3-dimethyluracil and mesitylene: formation of photocycloadducts and their characterization

Chem Pharm Bull (Tokyo). 2001 Apr;49(4):384-90. doi: 10.1248/cpb.49.384.

Abstract

In contrast to the previously reported short time required (1 h) for photolysis of 6-chloro-1,3-dimethyluracil (6-CIDMU) and mesitylene, in the presence of TFA, resulting in two major products: 1,3,6,8,10-pentamethylcyclooctapyrimidine derivative (1d), and diazapentacyclo[6.4.0.0(1,3).0(2,5).0(4,8)]dodecane (2c), prolonged irradiation (18h) of this same mixture yields novel pentalenopyrimidine derivatives, including diazapentacyclo[6.4.0.0(1,3).0(2,6).0(4,8)]dodecane (3c).

MeSH terms

  • Acids
  • Benzene Derivatives / chemistry*
  • Benzene Derivatives / radiation effects
  • Catalysis
  • Light
  • Magnetic Resonance Spectroscopy
  • Models, Molecular
  • Photochemistry
  • Photolysis
  • Trifluoroacetic Acid / chemistry
  • Uracil / analogs & derivatives*
  • Uracil / chemistry*
  • Uracil / radiation effects

Substances

  • Acids
  • Benzene Derivatives
  • Uracil
  • 6-chloro-1,3-dimethyluracil
  • mesitylene
  • Trifluoroacetic Acid