Stereoselective synthesis of tetrahydronaphthocyclobuta[1,2-d]pyrimidinediones from 5-fluoro-1,3-dimethyluracil and naphthalenes.
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.
Ohkura
Kazue
K
Faculty of Pharmaceutical Sciences, Health Sciences University of Hokkaido, Kita, Sapporo, Japan. ohkura@hoku-iryo-u.ac.jp
Ishihara
Tetsuya
T
Nishijima
Ken-ichi
K
Diakur
James Michael
JM
Seki
Koh-ichi
K
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*
C500872:5-fluoro-1,3-dimethyluracil; D007202:Indicators and Reagents; D009281:Naphthalenes; D011743:Pyrimidines; D014498:Uracil