Molecules 2012-01-01

Development of diversified methods for chemical modification of the 5,6-double bond of uracil derivatives depending on active methylene compounds.

Hironao Sajiki, Yusuke Iida, Kanoko Ikawa, Yoshinari Sawama, Yasunari Monguchi, Yukio Kitade, Yoshifumi Maki, Hideo Inoue, Kosaku Hirota

Index: Molecules 17(6) , 6519-46, (2012)

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Abstract

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.