Cyclisation of Propargyl and Allyl Amides: Syntheses of Oxazolines
|Institution:||University of Huddersfield|
|Full text PDF:||http://eprints.hud.ac.uk/24273/|
This thesis describes several approaches to the synthesis of dihydrooxazoles (oxazolines) by the cyclisation of unsaturated amides. The first major approach to the synthesis of substituted dihydrooxazoles is the CuI-catalysed cycloisomerisation of terminal propargyl amides. The reaction has been shown to have good substrate scope and experiments to delineate the mechanism have been performed. Substrates containing a benzylic methylene were oxidised to the ketone under the reaction conditions. The second major focus of this thesis is the cyclisation of N-alkenylamides catalysed by iodoarenes under oxidative conditions. Dihydrooxazoles were prepared by this route with a range of substitution patterns in good yields.