ORGN 125 |
| Indoles are among the most important and commonly found heterocyclic motifs in both pharmaceuticals and natural products. In the majority of syntheses the key nitrogen atom is incorporated early in the synthetic sequence. We wished to develop a synthesis in which the nitrogen atom was introduced as the final step of the route, allowing straightforward variation of the N-substituent. We have shown that efficient palladium catalysed ring-closing amination or amidation, involving both aryl and alkenyl C-N bond formation, is achieved by treatment of triflate 1 with aniline or propionamide to yield the tetrahydrocarbazoles 2 and 3 in good yields. The poster will expand upon these results, as well as showing how this method can be extended to include a variety of cyclic and acyclic ketones, a number of different N-sources including amines, amides, carbamates and sulfonamides as well a number of functionalised arenes to form a variety of indole derivatives.
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Heterocycles, Aromatics, Materials, Devices, Switches, Combinatorial Chemistry, Metal-Mediated Reactions
8:00 PM-10:00 PM, Sunday, 13 March 2005 Convention Center -- Hall D, Poster
Division of Organic Chemistry |
