Reductive debromination and coupling reaction in the thermolysis of 5-bromouracils in N,N-dialkylamides. Cleavage of the C(5)–bromine bond by an initial electron-transfer process

Abstract

Thermolysis of various 5-bromouracils (1) in N,N-dialkylamides results in the formation of methylenebisuracils (2) and reductive debrominated products (3)via cleavage of the C(5)–Br bond; the latter involves a one-electron transfer process. The product distribution between (2) and (3) depends upon the nature of substituents in the uracil ring.