A Novel Radical Access to Benzazepinones, Naphthylamides and Naphthylhydrazides

Abstract : The work presented in this manuscript highlights some further sometimes unusual aspects of the radical chemistry of xanthates. The study of the cyclisations onto the aromatic ring of hydroxamates has revealed an unexpected fragmentation and a brief investigation provided solid evidence for the homolytic rupture of the N-O bond. Consequently, a new methodology to access the family of N-unsubstituted benzazepinones based on the xanthate chemistry was developed. Benzazepinones with various substituents including sugar and boronate could be readily prepared by this route. The process is flexible, convergent and very suitable for the construction of libraries.Alpha-Tetralones are readily prepared by the xanthate-based addition/cyclisation sequence and are important intermediates for the synthesis of various aromatic structures. An efficient and general methodology to access regioselectively substituted naphthylamides by aromatisation of the corresponding alpha-tetralones was established. Naphthylhydrazides were synthesized in the same fashion, but in this case, the alpha-tetralones were reacted with Boc-protected hydrazines before undergoing the aromatisation.
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Submitted on : Tuesday, November 18, 2014 - 12:17:40 PM
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Ngoc Diem My Tran. A Novel Radical Access to Benzazepinones, Naphthylamides and Naphthylhydrazides. Chemical Sciences. Ecole Polytechnique, 2014. English. ⟨tel-01083982⟩

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