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Communication | Regular issue | Vol 57, No. 8, 2002, pp.1403-1408
Published online, 1st January, 1970
DOI: 10.3987/COM-02-9526
Photochemical Synthesis of Naphthocyclobutapyrimidines via 1,2-Cycloaddition of 6-Chloro-1,3-dimethyluracil with Naphthalenes

Kazue Ohkura, Shun Uchiyama, Kazuya Aizawa, Ken-ichi Nishijima, and Koh-ichi Seki*

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


UV-Irradiation of a solution of 6-chloro-1,3-dimethyluracil (6-ClDMU) and naphthalene in a non-polar solvent (cyclohexane) afforded 6-(1-naphthyluracil) as the sole product. In contrast, irradiation of a solution of 6-ClDMU and naphthalene in a polar medium in the absence of TFA effected 1,2-cycloaddition to give naphthocyclobutapyrimidines in moderate yields. This photocycloaddition reaction also proceeds in non-polar solvents in the presence of TFA.