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Communication | Special issue | Vol 59, No. 2, 2003, pp.459-464
Published online, 1st January, 1970
DOI: 10.3987/COM-02-S54
Acid-catalyzed Photocycloaddition of 6-Chloro-1,3-Dimethyluracil to Polycyclic Aromatic Hydrocarbons

Kazue Ohkura, Shun Uchiyama, Masayuki Sato, James M. Diakur, and Koh-ichi Seki*

*Faculty of Pharmaceutical Sciences, Health Sciences University of Hokkaido, Ishikari-Tobetsu, Hokkaido 061-0293, Japan

Abstract

The acid-catalyzed photoreaction of 6-chloro-1,3-dimethyluracil (6-ClDMU) with various polycyclic arenes was investigated: UV-Irradiation of a solution of 6-ClDMU with phenanthrene (1a), 9-cyanophenanthrene (1b) and pyrene (1f) in cyclohexane effected 1,2-cycloaddition to furnish the corresponding cyclobutapyrimidines as the predominant adducts, while the substitution reaction with acenaphthene (1e) and chrysene (1g) proceeded to give the corresponding 6-aryl-1,3-dimethyluracils.