Palladium-Catalyzed Approach to 1,2-Disubstituted Carbocyclic Nucleoside Analogues of 5-Alkynyl and 5-Alkenyl Uracil

Abstract

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.

Key words

nucleosides - heterocycles - cross-coupling - palladium

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