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Paper | Special issue | Vol 61, No. 1, 2003, pp.377-389
Published online, 9th October, 2003
DOI: 10.3987/COM-03-S54
Facil Synthesis of 4a-Fluoro-5,10-ethenobenzo[f]quinazolines through 1,4-Photocycloaddition of 5-Fluoro-1,3-dimethyluracil with Substituted Naphthalenes

Kazue Ohkura, Tatsuyuki Sugaoi, Tetsuya Ishihara, Kazuya Aizawa, Ken-ichi Nishijima, Yuji Kuge, and Koh-ichi Seki*

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


UV-irradiation of 6-chloro-1,3-dimethyluracil with naphthalenes underwent 1,2-cycloaddition to give naphthocyclobutapyrimidines consisting of a cyclobutene ring, The same reaction of an aprotic solution of 5-fluoro-1,3-dimethyluracil and naphthalenes bearing various substituents underwent 1,4-cycloaddition mode-selectively to give the corresponding ethenobenzoquinazoline derivatives with H and F atoms remaining intact on the newly constructed barrelene moiety. In protic solvents, the reaction preferentially proceeded by way of a substitution reaction to afford 5-(1-naphthyl)uracil.