ORGN 48 |
| Amy E. Hayden and Kostyantyn Kirichenko. Department of Chemistry, Center for Heterocyclic Compounds, University of Florida, PO Box 117200, Gainesville, FL 32611-7200 |
| Several enaminoketones were synthesized from imidoylbenzotriazoles and silyl enol ethers. Imidoylbenzotriazoles serve as important alternatives to imidoyl chlorides due to their enhanced stability. Imidoylbenzotriazoles can be synthesized from amides using 1-chloro-1H-benzotriazole and triphenylphosphine. In the reaction to synthesize enaminoketones, unwanted self-aldol condensation was curtailed by the use of silyl enol ethers in place of ketones, preventing hydrolysis of the imidoylbenzotriazoles. Target enaminoketones were synthesized using base-assisted nucleophilic substitution of imidoylbenzotriazoles by silyl enol ethers. Yields of 50 – 80 % were accomplished with this novel synthetic strategy. |
|
New Reactions and Methodology, Metal-Mediated Reactions, Heterocycles and Aromatics
8:00 PM-10:00 PM, Sunday, March 28, 2004 Anaheim Convention Center -- Hall A, Poster
Division of Organic Chemistry |