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Paper | Special issue | Vol 70, No. 1, 2006, pp.501-508
Published online, 17th November, 2006
DOI: 10.3987/COM-06-S(W)51
Photochemical Synthesis of Polycyclic Pyrimidines through the Acid Catalyzd Cycloaddition of 6-Chloro-1-methyluracil to Methyl Substituted Benzenes

Kazue Ohkura,* Takeshi Yamaguchi, 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-methyluracil with benzene in the presence of TFA resulted in 1,2-cycloaddition and susequent elimination of HCl gave a cyclooctapyrimidine-2,4-dione. Similar acid catalyzed photoreaction with substituted benzenes bearing two or three methyl groups afforded the corresponding cyclooctapyrimidines and two novel pentacyclic compounds, 9,11-diazapentacyclo[,3.02,5.04,8]dodecanes and 9.11-Å@diazapentacyclo[,3.02,6.04,8]dodcanes, in fair yields.