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Title: The synthesis of 5-substituted hydantoins
Authors: Murray, Ross George
Supervisors: Conway, Stuart J.
Keywords: Hydantoin
Lewis acid catalysis
Issue Date: 25-Jun-2008
Abstract: The Bucherer-Bergs reaction is a classical multi-component reaction that yields hydantoins, which can be hydrolysed to afford α-amino acids. Hydantoins have many uses in modern organic synthesis, and this moiety has been included in a number of therapeutic agents, which have a wide range of biological activities. Herein, we report a mild synthesis of 5- and 5,5-substituted hydantoins from α-aminonitriles using Hünig’s base and carbon dioxide. This reaction can be performed in excellent yields, using a variety of organic solvents and is applicable to a range of substrates. In an extension to the above methodology, a one-pot Lewis acid-catalysed synthesis of hydantoins from ketones has also been developed and optimised in organic media. This reaction can be performed in excellent yields and is suitable for the synthesis of 5- and 5,5-substituted hydantoins.
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Type: Thesis
Publisher: University of St Andrews
Appears in Collections:Biomedical Sciences Research Complex (BSRC) Theses
Chemistry Theses

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