ORGN 760 |
| The Bucherer-Bergs reaction is a classical multi-component reaction that yields hydantoins, which can be hydrolysed to afford amino acids. However, hydantoins also 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. The conditions employed in the classical Bucherer-Bergs reaction are often harsh, including polar solvents and heating. A recent alternative to hydantoin synthesis has been developed, where alpha-amino amides are transformed to hydantoins in the presence of triphosgene. Herein, we report a mild synthesis of hydantoins from aminonitriles using Hunig's base and carbon dioxide (Fig. 1). 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 is currently being optimised (Fig. 2).
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Combinatorial, Parallel and Process Chemistry, Heterocycles, Aromatics, New Reactions and Methodology
8:00 PM-10:00 PM, Wednesday, August 22, 2007 BCEC -- Exhibit Hall - B2, Poster
Division of Organic Chemistry |
