ORGN 141 |
| Indoles are important heterocycles present in a wide variety of natural products and pharmaceuticals. Although the synthesis of 2-carboxy substituted indoles is well documented, relatively little has been published on the analogous azaindoles. The present study describes a facile and general synthesis of a series of substituted 5, 6, and 7-azaindoles via the Hemetsberger-Knittel reaction to provide a core structure which is isosteric to the analogous indoles, yet more electron deficient. The thermolysis reaction of the intermediate azidopyridine acrylate is tolerant of various solvents, and yields are good in most cases, especially for the 5- azaindoles. Higher temperatures are generally required compared to the formation of the indole analogues, and in some instances, it was found that only decomposition occured below a minimum threshold temperature. The resulting templates also offer up to 5 different sites for further functionalization.
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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 |
