Development of Diversified Methods for Chemical Modification of the 5,6-Double Bond of Uracil Derivatives Depending on Active Methylene Compounds

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.

Synthesis, Characterization and Crystal Structure of 4-Dichloroacetyl-2,5-dimethyl-8-oxo-1,4-diazabicyclo[3.3.0]octane

“…Diazabicyclo derivatives attracted more attention in organic synthesis for their widely used as a structure-directing agent 1 , synthons 2,3 , catalysts 4 , etc. They were also the target compounds for their versatile bioactivity [5][6][7][8] . Since BASF employed BAS-145138 as safeners which increased the toleration of crops to herbicidal acetanilides 9 , dichloroacetyl diazabicyclo derivatives were reported as a novel kind of herbicide safener protecting crops from injury by chlorine acetamide herbicides, sulfonylurea herbicides and imidazolinone herbicides 10,11 .…”