Synthese et reactivite en serie heterocyclique

Abstract

The problematic of the thesis is to propose new ways of access to a wide variety of new molecules presenting a great functional and structural diversity, and potentially a biological interest. The discovery of the thiazolidinone heterocycle and its analogues dates back more than 50 years, as bioactive compounds that are widely applied in the pharmaceutical field. The first chapter of this manuscript aims at the synthesis of 5-arylidene-2-thioxothiazolidin-4- ones derivatives, particular structures with a wide range of functionality. In order to value the prepared products, we were interested in the reactivity of the basic cycle ""Rhodanine"" as well as the 5-ene derivatives. Another privileged structure and a high class in all oxygenated heterocycles is the chromene backbone, which is a structural feature of more complex compounds, including both natural and synthetic molecules. Our second chapter is dedicated to a multi-step synthesis, aimed at the synthesis of 4- methylenechromane-2-carboxylate derivatives. The peculiarity of this methodology is the use of borylated intermediates. The responsiveness of the final products as well as some key intermediates have been studied, furthermore, interesting transformations encountered during the synthesis. In the last chapter, we will focus on the catalytic study of a multicomponent Reaction, those one-step synthesis tools that provide structural complexity with lower costs. The reaction of an aromatic aldehyde, malononitrile and dimedone in an aqueous system was carried out with pyridinium p-toluenesulfonate as a catalyst, its acidity and its association to an ionic liquid in terms of structure have ensured the catalysis of this reaction to give 2- amino-4H-chromene-3-carbonitriles.