Development of diversified methods for chemical modification of the 5,6-double bond of uracil derivatives depending on active methylene compounds.
The reaction of 5-halogenouracil and uridine derivatives 1 and 7 with active methylene compounds under basic conditions produced diverse and selective C-C bond formation products by virtue of the nature of the carbanions. Three different types of reactions such as the regioselective C-C bond formation at the 5- and 6-positions of uracil and uridine derivatives (products 2, 5, 8, 17, 20 and 21), and the formation of fused heterocycle derivatives 2,4-diazabicyclo[4.1.0]heptane (15) and 2,4-diazabicyclo-[4.1.0]nonane (16) via dual C-C bond formations at both the 5- and 6-positions were due to the different active methylene compounds used as reagents.
Laboratory of Organic Chemistry, Gifu Pharmaceutical University, 1-25-4 Daigaku-nishi, Gifu 501-1196, Japan. sajiki@gifu-pu.ac.jp
Hironao
H
Sajiki
Yusuke
Y
Iida
Kanoko
K
Ikawa
Yoshinari
Y
Sawama
Yasunari
Y
Monguchi
Yukio
Y
Kitade
Yoshifumi
Y
Maki
Hideo
H
Inoue
Kosaku
K
Hirota
D014498:Uracil / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry; D014529:Uridine / Q000031:analogs & derivatives / Q000138:chemical synthesis / Q000737:chemistry
D014498:Uracil; D014529:Uridine