Eine neue Methods zur Einführung von CF3‐ und C2F5‐Gruppen in Pyrimidinderivate und die Anti‐Herpes‐Aktivität der Verbindungen

A New Method of the Introduction of CF3‐ and C2F5‐Groups into Pyrimidine Derivatives and their Antiherpes Activity A new method of the perfluoroalkylation of uracil derivatives is described. The irradiation of aqueous solutions of uracil and uracilnucleosides with bis‐(perfluoroalkyl) mercury (CnF2n+1)2Hg n = 1, 2 under the exclusion of oxygen in the presence of catalytic amounts of azo‐bis‐isobutyronitril at 254 nm for several hours gave new 5‐perfluoroalkylated compounds. In this way we obtained 5‐trifluoromethyluracil (5a), 5‐pentafluoroethyluracil (5b), 5‐trifluoromethyl‐2′‐deoxyuridine (6a), 5‐pentafluoroethyl‐2′‐deoxyuridine (6b) and 1‐(ß‐D‐arabinofuranosyl)‐5‐trifluoromethyluracil (7a) in different yields. The perfluoroalkylated compounds were tested against HSV‐1 and HSV‐2 viruses on human lungefibroblasts. The compounds are markedly less potent than other known nonfluorinated compounds.