Direct methods for the preparation of heterocycles and bis-heteroaromatics

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Within this project we will develop new reagent based methodology to provide simple, robust and highly practical synthetic methods of broad applicability within organic synthesis. N-Methyl-O-tosyl hydroxylamine will provide a new method for the direct conversion of both aldehydes and ketones to alpha-oxysulfonyl carbonyl compounds, which, when treated directly with a variety of bis-hetero nucleophiles in-situ will provide a one-pot reaction sequence to access a variety of biologically significant heterocycles. Buchwald coupling of N-methyl-O-benzoyl hydroxylamine (and analogues) with aryl halides will lead to a cascade reaction sequence to provide direct access to bis-functionalised heteroaromatics which are present in a wide variety of both synthetic and naturally occurring compounds of biological importance. Application of these new methods to the praparation of targeted chemical arrays will provide access to a series of densely functionalised products for biological assay.