title: Stereoselective synthesis of tetrahydronaphthocyclobuta[1,2-d]pyrimidinediones from 5-fluoro-1,3-dimethyluracil and naphthalenes.
abstract: Upon UV-irradiation in the presence of piperylene, 5-fluoro-1,3-dimethyluracil (5-FDMU) couples with naphthalenes having either an electron-withdrawing group or an electron-donating group by way of 1,2-cycloaddition via mode selectivity to give the corresponding naphthocyclobutapyrimidines regio- and stereo-selectively.
authors.affiliation: Faculty of Pharmaceutical Sciences, Health Sciences University of Hokkaido, Kita, Sapporo, Japan. ohkura@hoku-iryo-u.ac.jp
authors.forename: Kazue
authors.initials: K
authors.lastname: Ohkura
authors.forename: Tetsuya
authors.initials: T
authors.lastname: Ishihara
authors.forename: Ken-ichi
authors.initials: K
authors.lastname: Nishijima
authors.forename: James Michael
authors.initials: JM
authors.lastname: Diakur
authors.forename: Koh-ichi
authors.initials: K
authors.lastname: Seki
mesh_terms: D003500:Cyclization; D004583:Electrons; D007202:Indicators and Reagents; D009682:Magnetic Resonance Spectroscopy; D013058:Mass Spectrometry; D009281:Naphthalenes / Q000737:chemistry*; D011743:Pyrimidines / Q000737:chemistry*; D016339:Spectrometry, Mass, Fast Atom Bombardment; D013237:Stereoisomerism; D014466:Ultraviolet Rays; D014498:Uracil / Q000031:analogs & derivatives* / Q000737:chemistry*
chemical_list: C500872:5-fluoro-1,3-dimethyluracil; D007202:Indicators and Reagents; D009281:Naphthalenes; D011743:Pyrimidines; D014498:Uracil