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 <strong>1</strong> and <strong>7</strong> 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 <strong>2</strong>, <strong>5</strong>, <strong>8</strong>, <strong>17</strong>, <strong>20</strong> and <strong>21</strong>), and the formation of fused heterocycle derivatives 2,4-diazabicyclo[4.1.0]heptane (<strong>15</strong>) and 2,4-diazabicyclo-[4.1.0]nonane (<strong>16</strong>) via dual C-C bond formations at both the 5- and 6-positions were due to the different active methylene compounds used as reagents.

Keywords

• C-C bond formation
• active methylene
• carbanion
• uracil
• uridine