ORGN 435 |
| There is considerable interest in the synthesis of heterocyclic compounds derived from hetero-'ene-ene-yne' precursors. The ring-forming reactions often proceed via unusual mechanisms as well as give rise to heterocycles with substitution patterns that would otherwise be hard to obtain. Advances in our lab have shown that 'azo-ene-yne' systems react either thermally or with the aid of a transition metal to form five- (isoindazole) or six- (cinnoline) membered ring systems in good to excellent yields. Replacement of the ethynyl unit with a cyano group (azo-ene-nitrile) also affords heterocycles under Lewis acidic conditions. Current work is focusing on the ability of imine-ene-yne systems to participate in analogous reactions. Density Functional Theory (DFT) has been successfully used with these systems to decipher potential mechanisms. This presentation will describe our latest experimental and computational results.
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Modern Acetylene Chemistry
8:00 PM-10:00 PM, Tuesday, 12 September 2006 Moscone Center -- Hall D, Poster
Division of Organic Chemistry |
