ORGN 390 |
| Imidazoles represent the core structure of a range of important therapeutics, including antitumor and anti-inflammatory agents. While there are a number of synthetic routes to imidazoles, these typically involve multi step synthesis, which limit the diversity of these compounds readily available. We have been investigating an alternative palladium catalysed synthesis of tetrasubstitued imidazoles. This process involves the formation of 1,3 oxazolium-5-oxide (Münchnone) intermediate, via palladium catalysed coupling of imine, acid chloride and carbon monoxide. The Münchnone intermediate can undergo a 1,3-dipolar cycloaddition with N-tosylimines to provide an overall one-pot synthesis of imidazoles. This catalytic synthesis can be generalized to a range of imidazoles via simple variation of imine or acid chloride building blocks. Furthermore, the utility of this multi component coupling reaction towards the generation of π-conjugated materials is also being explored.
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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 |
