El qacemi, Myriem (2005) Synthesis of various heterocycles via a new radical process. PhD thesis DCSO, EP - DCSO Laboratoire de Synthèse Organique, EP/X p.362.

Alternative Locations: http://www.imprimerie.polytechnique.fr/Theses/Files/Qacemi.pdf

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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