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Communication | Regular issue | Vol 53, No. 6, 2000, pp.1247-1250
Published online, 1st January, 1970
DOI: 10.3987/COM-00-8880
Photochemistry of 9,10-Dihydro-1,3,5,7-tetramethyl-9-methylenecylooctapyrimidine-2,4-dione: Synthesis of Novel Ring Systems through Electrocyclic Reactions

Kazue Ohkura, Ken-ichi Nishijima, Akiyo Sakushima, and Koh-ichi Seki*

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

Abstract

Photolysis of 1,3,5,7,9-pentamethylcyclooctapyrimidine-2,4-dione (1a) prepared by the photoreaction of 6-chloro-1,3-dimethyluracil with mesitylene in the presence of TFA at low temperature resulted in the formation of the 9-exo-methylene derivative (2), which was further converted into a novel cyclopropa-pentalenopyrimidine (5) and a cyclobutaquinazoline (3) through [4 + 2] and [2 + 2] electrocyclic reactions, respectively. The latter (3) was ultimately transformed into the 9,11-diazapentacyclo[6.4.0.01,3.02,5.04,8]dodecane-2,4-dione derivative (4).