Compuestos nitrogenados fluorados:síntesis y reactividad.

by Piera Balaguer, Julio

ABSTRACT The thesis is divided in three chapters distributed in introduction, objectives, background, results and experimental part. Chapter 1. It has two different parts: In the first part, the synthesis of chiral fluorinated oxazolidinones is described. The starting materials for the synthesis are fluorinated imidoyl chorides. In the second part, the reactivity and diastereoselectivity of the fluorinated oxazolidinones are studied in comparison with the non-fluorinated oxazolidinone in alquilation and aldolic reactions. Chapter 2. The chapter is divided in three parts. 1º. An efficient and convenient two-step synthesis of new fluorinated uracils is described. The first step involves the condensation of an ester enolate with a fluorinated nitrile to furnish fluorinated b-enamino esters. In turn, these compounds react with organic isocyanates or isothiocyanates to give C-6 fluorinated uracils or thioruacils, respectively, in excellent yields. 2º. This synthesis has been succesfully adapted to solid-phase conditions with high diversity, thereby facilitating the creation of small (thio)uracil libraries. 3º.The synthesis of new bicyclic uracils is described. The key step is a metathesis reaction. Chapter 3: The synthesis of fluorinated 2-pyrimidinones is described in this chapter. The first step involves the condensation of an imine enolate with a fluorinated nitrile to furnish fluorinated b-diimines. The reaction of the last with triphosgene afford the objective compounds.