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Synthèse et fonctionnalisation de nouveaux hétérocycles fusionnés à motif quinuclidine

Abstract : For more than a century, heterocycles have become compounds of interest due to their efficacy in various fields such as pharmaceuticals, agriculture or cosmetics. With the introduction of high throughput screening, it has become necessary to develop libraries of molecules to cover the most chemical space. In this contest of diversity-oriented synthesis and to “escape the Flatland”, we have been interested in the synthesis and functionalization of fused heterocycles containing nitrogen such as the quinuclidine moiety, which is present in natural and synthetic molecules of therapeutic interest such as quinine. In the first hand, we have study the synthesis of new versatile platforms with a quinuclidine moiety fused with heterocycle containing nitrogen atom such as 5,8-ethanopyrido[3,2-d]pyrimidine, 1,4-ethano-1,5-naphthyridine and 4,7-ethanopyrazolo[4,3-b]pyridine. We then focused our research to create C-C or C-heteroatom bounds with several functionalization methodologies such as palladium-catalyzed cross-coupling or SɴAr using modern synthesis techniques.In a second hand, we decided to apply a new technology, the flow chemistry, to the derivatives of 1,4-ethano-1,5-naphthyridine through the transposition of the Suzuki-Miyaura cross-coupling and the aldolization-crotonization reaction in order to reduce the reaction time and limit the problem of reactivity.
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Submitted on : Tuesday, May 10, 2022 - 12:01:18 PM
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Mazarine Laurent. Synthèse et fonctionnalisation de nouveaux hétérocycles fusionnés à motif quinuclidine. Chimie organique. Université d'Orléans, 2020. Français. ⟨NNT : 2020ORLE3075⟩. ⟨tel-03663615⟩

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