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Title: The synthesis of 5-substituted hydantoins
Author: Murray, Ross G.
ISNI:       0000 0004 2716 8604
Awarding Body: University of St Andrews
Current Institution: University of St Andrews
Date of Award: 2008
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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.
Supervisor: Conway, Stuart J. Sponsor: sanofi-aventis
Qualification Name: Thesis (Ph.D.) Qualification Level: Doctoral
EThOS ID:  DOI: Not available
Keywords: Hydantoin ; Aminonitrile ; Synthesis ; Lewis acid catalysis ; QD401.M8 ; Hydantoin--Synthesis