Intramolecular ene reactions of functionalised nitroso compounds

• Main Author: Luengo Arratta, S.
• Published: University College London (University of London) 2010
• Subjects: 540
• Online Access: http://ethos.bl.uk/OrderDetails.do?uin=uk.bl.ethos.564998

This thesis concerns the generation of geminally functionalised nitroso compounds and their subsequent use in intramolecular ene reactions of types I and II, in order to generate hydroxylamine derivatives which can evolve to the corresponding nitrones. The product nitrones can then be trapped in the inter- or intramolecular mode by a variety of reactions, including 1,3-dipolar cycloadditions, thereby leading to diversity oriented synthesis. The first section comprises the chemistry of the nitroso group with a brief discussion of the current methods for their generation together with the scope and limitations of these methods for carrying out nitroso ene reactions, with different examples of its potential as a powerful synthetic method to generate target drugs. The second chapter describes the results of the research programme and opens with the development of methods for the generation of functionalised nitroso compounds from different precursors including oximes and nitro compounds, using a range of reactants and conditions. The application of these methods in intramolecular nitroso ene reactions is then discussed. Chapter three presents the conclusions which have been drawn from the work presented in chapter two, and provides suggestions for possible directions of this research in the future. This work concludes with a formal account of the experimental procedures.