Various pentafluoropropenyl derivatives of pyrimidine and purine bases have been obtained in good to high yield. The procedure involves the reaction of appropriate lithium derivatives prepared from both electron-rich and electron-poor pyrimidines, with the hexafluoropropene at a low temperature, via an addition-elimination process. Organolithiums of pyrimidine and purine bases give addition-elimination products as E/Z mixtures, whereas the products of the reaction of lithium amide of protected inosine with hexafluoropropene contain traces of an addition product as well as the stable perfluoroenamine. The methodology proposed allows a series of perfluorovinyl nucleobases to be obtained quickly and conveniently.

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The title compounds are of biological interest. -(WOJTOWICZ-RAJCHEL, H.; MIGAS, M.; KORONIAK*, H.; J. Org. Chem. 71 (2006) 23, 8842-8846; Fac. Chem., Adam Mickiewicz Univ., PL-60-780 Poznan, Pol.; Eng.) -Jannicke 12-162