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Paper | Regular issue | Vol 57, No. 4, 2002, pp.665-676
Published online, 1st January, 1970
DOI: 10.3987/COM-02-9451
Photocycloaddition of 6-Cyano-1,3-dimethyluracil to Alkenes; Synthesis of Tetrahydrocyclobutapyrimidine-6a-carbonitriles

Kazue Ohkura, Hideaki Nakamura, Tatsuyuki Sugaoi, Akiyo Sakushima, Hajime Takahashi, and Koh-ichi Seki*

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


UV-Irradiation of 6-cyano-1,3-dimethyluracil (6-CNDMU) and alkenes having electron-donating and electron-withdrawing groups afforded the corresponding cyclobutapyrimidine derivatives with head-to-tail regiochemistry in appreciable yields. Similarly 6-CNDMU coupled with 6-CNDMU or 1,3-dimethyluracil to give trans-syn type cyclobutene pyrimidine dimers, while the reaction with 1,3-dimethylthymine proceeded the coupling reaction non-regio- and stereoselectively.