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Nouvelles réactions radicalaires. Application à la synthèse d'hétérocycles azotés.

Abstract : We have envisioned new applications of the xanthate transfer radical chemistry developed over the past decade in our laboratory. A first part deals with the development of a free radical xanthate-mediated cyclisation or intermolecular addition/cyclisation sequence for the construction of new pyridine fused rings. The unusual flexibility of the free-radical cyclisation using xanthates allowed us to construct various rings in very few steps often in a convergent manner. This method employs cheap and non-toxic reagents, and the reactions are easily carried out. Several members of the family of azaoxindoles, azaindolines, azaindoles, tetrahydronaphtyridines, dihydronaphtyridinones and tetrahydropyridoazepinones were successfully prepared. A second part reports the use of a new xanthate derived from a-chloroacétone to access with great flexibility complex molecules. Studies towards the formal synthesis of a natural product, perhydrohistrionicotoxine, were also investigated. Eventually, a novel radical Smiles rearrangment, discovered during the course of this work, has been studied.
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Submitted on : Thursday, July 29, 2010 - 10:07:58 AM
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Myriem El Qacemi. Nouvelles réactions radicalaires. Application à la synthèse d'hétérocycles azotés.. Chimie organique. Ecole Polytechnique X, 2005. Français. ⟨pastel-00002117⟩

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