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2005
Fused pyrimidine derivatives
R 0515
Stereoselective Synthesis of Tetrahydronaphthocyclobuta[1,2-d]pyrimidinediones
5-Fluoro-1,3-dimethyluracil and Naphthalenes. — The addition of the triplet
32- 153 from
quencher piperylene changes the mode of the cycloaddition of the uracil (I) with substituted naphthalenes from 1,4-addition to 1,2-cycloaddition. The latter reaction proceeds with naphthalenes having both electron-donating and electron-withdrawing
groups to give stereoselectively the corresponding 1,2-adducts (IV), (VI) and (VIII) in
fair yields. The regioselectivity depends on the electronic properties of the substituents
on the naphthalene ring. — (OHKURA*, K.; ISHIHARA, T.; NISHIJIMA, K.-I.;
DIAKUR, J. M.; SEKI, K.-I.; Chem. Pharm. Bull. 53 (2005) 2, 258-259; Fac. Pharm.
Sci., Health Sci. Univ. Hokkaido, Hokkaido 061, Japan; Eng.) — H. Haber
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