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Des isonitriles aux pyruvamides : Nouveaux développements des réactions de Ugi et phospha-Brook.

Abstract : A great part of this thesis is dedicated to chemistry of isocyanides: thus several chapters treat interactions between isocyanides and acids derivatives, a significant part was devoted there to the valorization of the fluorinated pyruvamides obtained by addition of isocyanides on trifluor! oacetic anhydride . It was thus possible to show the interest of the hydrates of trifluoropyruvamides as a electrophiles with respect to ketones and nitrated derivatives. Pinacolic attempts couplings of pyruvamides thereafter involved us towards the study of a very original aromatic aldehyde reduction by the dimethylphosphite. The mechanism probably implies a Phospha-Brook type rearrangement with direct benzylic phosphate formation. Some synthetic applications of this reaction were tested before reconsidering the chemistry of isocyanides. We could combine a Ugi type reaction with a cyclization of N-acyliminium in a very short synthesis of tricyclic diketopiperazines . This work already led to the publication of three communications, several projects initiated in this thesis will be continued, the coupling between the chemistry of isonitriles and cyclizations of N-acylimminiums seeming particularly promising.
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Submitted on : Wednesday, July 28, 2010 - 2:04:10 PM
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Laetitia Gaultier. Des isonitriles aux pyruvamides : Nouveaux développements des réactions de Ugi et phospha-Brook.. Génie chimique. Ecole Polytechnique X, 2005. Français. ⟨pastel-00001908⟩

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