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Communication | Special issue | Vol 66, No. 1, 2005, pp.143-146
Published online, 8th November, 2005
DOI: 10.3987/COM-05-S(K)55
Direct C-C Bond Formation between Thymine Derivatives and Naphthalene through [2+2]-Photocycloaddition

Kazue Ohkura,* Tetsuya Ishihara, Hajime Takahashi, Haruko Takechi, and Koh-ichi Seki*

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

Abstract

In contrast to our previous findings that UV-irradiation of 1,3-dimethylthymine (1a) with naphthalene (2) underwent 1,4-cycloaddition to give an ethenobenzoquinazoline derivative, UV-irradiation of a mixture of 1a and 2 in the presence of piperylene preferentially underwent 1,2-cycloaddition to give cis-tetrahydronaphthocyclobutapyrimidine in high stereoselectivity. Similar irradiation of 1,3-dimethyluracil and its derivatives (1) with substituents at C-5 gave the corresponding cis-1,2-adducts (3) in fair yields.