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Contribution à la chimie des cinnamates ortho-fonctionnalisés : Exploitation comme (1) précurseurs synthétiques d'hétérocycles, (2) antennes photoactivables de complexes d'ions lanthanides luminescents

Abstract : The chemistry of ortho-functionalized cinnamates is particularly rich and varied, as evidenced by the large number of methods using them as building blocks for the synthesis of biologically-relevant heterocycles. In fact, depending on the nature of the functional group and the reaction conditions, various cinnamic-based substrates have already been successfully employed for the synthesis of a wide range of heterocyclic skeletons, ranging from five-membered ring systems (benzofuran, indole, ...) to six-membered rings (coumarin, quinolin(on)e, ...). In this context, the main goal of my thesis was to make a significant contribution to the chemistry peculiar to ortho-functionalized cinnamates. The first objective of my work dealt with the development of new methods for heterocyclic synthesis using ortho-functionalized cinnamates as building blocks. On one hand, a method for the regioselective synthesis of 3-trifluoromethylated coumarins and quinolones was elaborated starting from ortho-hydroxy- and ortho-aminocinnamates. The reaction mechanism of this trifluoromethylation reaction was further investigated and was found to involve radical participation. On the other hand, ortho-azidocinnamates proved suitable building blocks to achieve the construction of indoles and quinolines via a solvent-dependent photochemical process. The second objective of my work was devoted to the design, synthesis and photophysical/photochemical evaluation of new photoactivatable luminescent probes based on lanthanide ions. In this case, a non-luminescent lanthanide complex was equipped with a cinnamoyl residue in order to act as a photoactivatable sensitizer. A preliminary study allowed us to validate the concept "OFF/ON", and then a series of probes was prepared in order to establish relevant structure-property relationships, hence enabling the optimization of this novel class of photoactivatable luminescent probes.
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Slim Chaabouni. Contribution à la chimie des cinnamates ortho-fonctionnalisés : Exploitation comme (1) précurseurs synthétiques d'hétérocycles, (2) antennes photoactivables de complexes d'ions lanthanides luminescents. Chimie organique. Université Paul Sabatier - Toulouse III, 2017. Français. ⟨NNT : 2017TOU30104⟩. ⟨tel-01903111⟩

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