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Nouvelles applications de la chimie radicalaire des xanthates à la synthèse d'hétérocycles azotés

Abstract : This thesis presents the work carried out under the guidance of Professor Samir Z. Zard in the laboratory DCSO at the Ecole Polytechnique from September 2006 to July 2009. We investigated new applications of xanthates radical chemistry to the synthesis of heterocyclic nitrogen compounds, such as oxindoles, azaindolines, dihydropyrrolopyrimidines, dihydropyrrolopyrimidinones and dihydroimidazopyrimidinones. Two main results stand out in this work: Firstly we put into general use the radical cyclization onto aromatic nitrogen, which was previously discovered in the laboratory with simple pyridines. We extended this reaction to other heterocyclic families (pentachloropyridine and pyrimidine). This methodology allowed us to synthesize innovative aromatic cores rarely described in the literature, such as dihydroimidazopyrimidinones. Secondly, during the synthesis of fluoroazaindolines, we evidenced the homolytic rupture of a carbon-fluoride bond under “mild conditions”. As far as we know, such a fragmentation is quite rare.
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Submitted on : Monday, February 21, 2011 - 11:22:23 PM
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Yann Laot. Nouvelles applications de la chimie radicalaire des xanthates à la synthèse d'hétérocycles azotés. Chimie organique. Ecole Polytechnique X, 2011. Français. ⟨pastel-00567807⟩

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