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Synthèse organométallique de composés bicycliques aza-p-déficients d'intérêt biologique potentiel

Abstract : This thesis presents two principles aspects: the first one consists in a regioselective metallation methodologic study of aza-p-deficients systems, and the second one, in the synthesis of highly biological interest scaffolds by organometallic way and / or transition metals couplings. So, in a first chapter, we describe the different results of the reaction between the superbasic complex [n-BuLi / LiDMAE] on p-deficient systems such as 7-azaindole or pyrazine. We also present results of other but close superbasic systems [s-BuLi / LiDMAE], [t-BuLi / LiDMAE], [LDA / LiDMAE], [LTMP / LiDMAE] on a model substrate: 3-chloropyridine. Indeed, this substrate allowed us to study regioselectivity and Basicity / Nucleophilicity ratio aspects. The second part of this thesis describes the synthesis of functionalised and functionalisable bicyclic targets especially containing a nitrogen atom such as pyrano[3,2-b]pyridine and oxepino[3,2-b]pyridine using an organometallic way, followed by transition metal couplings and ring closing metathesis. For this last step, we studied the efficiency of first and second generation Grubbs catalysts, comparing each, and optimising for each the yield of product obtained compared to the amount of catalyst introduced. Finally, we envisioned the formation of thieno[3,2-b]pyridines functionalised and functionalisable by regioselective lithiation of 3-methylthiopyridine followed by Sonogashira coupling and electrophilic cyclisation.
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Estelle Banaszak. Synthèse organométallique de composés bicycliques aza-p-déficients d'intérêt biologique potentiel. Biologie moléculaire. Université Henri Poincaré - Nancy 1, 2007. Français. ⟨NNT : 2007NAN10007⟩. ⟨tel-01775997⟩

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