Journal of the American Chemical Society, Vol.118, No.43, 10408-10411, 1996
Elemental Fluorine to 8-Fluoropurines in One-Step
An efficient regiocontrolled approach to the synthesis of 8-fluoropurines by direct fluorination of purines with dilute elemental fluorine is described. The one-step procedure produced regiospecific substitution of the C(8)-hydrogen of purine derivatives in isolated yields close to 30% with protected purines in CHCl3. Fluorination yields with unprotected purines in EtOH were reduced to less than 10%. The electrophilic fluorination procedure has a broad scope of applicability and permits a ready and easy access to 8-fluoropurine derivatives, for the first time, for evaluation of their biochemical and pharmacological properties.
Keywords:ACID RELATED-COMPOUNDS;ACETYL HYPOFLUORITE;ADENOSINE-DEAMINASE;PURINE NUCLEOSIDES;REGIOSELECTIVE RADIOFLUORODESTANNYLATION;SELECTIVE FLUORINATION;BIOLOGICAL EVALUATION;ORGANIC-COMPOUNDS;CONFORMATION;DERIVATIVES