Maria J. Gonzalez Moa

Palladium-catalyzed approach to 1,2-disubstituted carbocyclic nucleoside analogues of 5-alkynyl and 5-alkenyl uracil

The preparation of new analogues of 5-alkynyl- and 5-alkenyl-uracil is described. The synthesis involved palladium-catalyzed C-C coupling reactions, with the 5-ethynyl, 5-(1-hexynyl), and 5-(2-phenylethynyl) derivatives prepared through a Sonogashira coupling. A Stille coupling reaction was used to obtain the 5-(1-hexynyl) derivative, whilst the (E)-5-(2-bromovinyl) derivative was prepared using the Heck reaction. All the methods were clean and simple to perform.