ORGN 733 |
| 2-Propenyl-4,4-dimethyl-2-oxazoline reacts with N-chlorocarbonyl isocyanate (ClCONCO), in the presence of triethylamine and with acetonitrile or tetrahydrofuran as solvent, give fused ring heterocyclic compound 1. The underlying mechanism is cyclocondensation between the 1,3-dielectrophile, ClCONCO, with the 1,3-dinucleophile, 2-propenyl-4,4-dimethyl-2-oxazoline. The resulting molecule is of interest because the exocyclic double bond is both an enamine and a vinyl ether, while also being a diene and an á,â-unsaturated ketone, simultaneously. Similar reactions with á,á-disubstituted diacyl chloride give densely functionalized fused ring system 2. Reactions of 2-propenyl-2-oxazolines, 2-propenyl-2-oxazines and their thiazoline and thiazine counterparts, with ClCONCO and other 1,3-dielectrophiles, like ClSO2NCO, are being explored.
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Combinatorial, Parallel and Process Chemistry, Heterocycles, Aromatics, New Reactions and Methodology
8:00 PM-10:00 PM, Wednesday, August 22, 2007 BCEC -- Exhibit Hall - B2, Poster
Division of Organic Chemistry |
