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Développement de nouvelles méthodologies pour la synthèse de spirotétrahydro-β-carbolines

Abstract : The aim of this work was to optimize a new way of synthesis of spirotetrahydro-β-carbolines. A three-steps strategy from the 3-(2-nitrovinyl)indole was elaborated with the following linear sequence : Michael addition, reduction of the nitro function into amine and Pictet-Spengler cyclisation. Michael addition was developed without protection of the indole under sonication activation. Reduction of the nitro function into amine was carried out with hypophosphites. During this study, desoxygenation of aromatic ketones has been identified as a side reaction of the reduction and has been the subject of specific development. A new synthetic pathway to functionalized isatins on C-5 position via substitution of diazonium salts was developed, and Heck-Matsuda reaction has been more particularly studied. The final Pictet-Spengler reaction between tryptamines and isatins led to tetrahydro-β-carbolines. Finally, biological activity of spirotetrahydro-β-carbolines was evaluated and one of these compounds showed good activity against Plasmodium falciparum
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Submitted on : Tuesday, April 29, 2014 - 3:47:40 PM
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  • HAL Id : tel-00985371, version 1


Marc Baron. Développement de nouvelles méthodologies pour la synthèse de spirotétrahydro-β-carbolines. Autre. Université Claude Bernard - Lyon I, 2014. Français. ⟨NNT : 2014LYO10002⟩. ⟨tel-00985371⟩



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