ORGN 398 |
| Benzoazepines are versatile building blocks for the preparation of biologically active compounds. Herein, the synthesis of benzo[d]azepin-2-one compounds via palladium-catalyzed intramolecular cyclization of o-alkynyl benzeneacetamides has been investigated. Benzeneacetamides with various acetylenic and N-substitutions were prepared. It was found that the 7-endo addition of nucleophilic amides to alkynes occurred in the presence of Pd catalysts and bases such as KOH. The desired seven-membered heterocyclic compounds were obtained in good yields. This specific regioselectivity is determined by substituents on the acetylene unit. The methodology provides an unprecedented and interesting method for establishing benzoazepine rings. The reaction scope and generality will also be presented. |
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Bioorganic, Metal-Mediated Reactions, and Molecular Recognition
8:00 PM-10:00 PM, Tuesday, 30 August 2005 Washington DC Convention Center -- Hall A, Poster
Division of Organic Chemistry |