ORGN 527 |
| Twisted amides, in which the amide bond deviates significantly from the planar conformation, are of interest from both a structural and reactivity perspective. Such amides are viewed as unstable and typically undergo reactions that are more commonly associated with ketones than amides. These features have been ascribed to the loss of the conjugation between the amide nitrogen and the C=O π bond. We reported a new series of stable twisted amides that have been synthesized using the intramolecular Schmidt reaction. The features that influence the relative amounts of twisted versus standard lactams will be discussed. It has also been shown that these twisted amides undergo facile regioselective C-N bond cleavage reactions under several kinds of conditions (H2/Pd(OH)2, DDQ, and MeI). Theses results, along with a discussion of the hydrolytic stability of the lactams toward hydrolysis, will be discussed.
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New Reactions and Methodology, Heterocycles and Aromatics, Bioorganic Chemistry
8:00 PM-10:00 PM, Tuesday, 12 September 2006 Moscone Center -- Hall D, Poster
Division of Organic Chemistry |