ORGN 796 |
| This poster describes the development of a facile synthetic procedure to construct 2H-quinolizin-2-one scaffolds from various substituted/aza 2-picoline precursors. Formation of the benzylic anion via LiHMDS or LDA deprotonation, followed by treatment with ethyl 3-(trimethylsilyl)prop-2-ynoate produces the 1-pyridin-2-yl-4-(trimethylsilyl)but-3-yn-2-one intermediate. Removal of the silyl protecting group and thermal cyclization yields the 2H-quinolizin-2-one scaffold in good yield. Instances where a 3-alkyl or phenyl prop-2-ynoate are used, acylation and cyclization conditions were optimized to yield a one pot two step procedure to generate 4-alkyl/aryl 2H-quinolizin-2-ones from picoline derivatives.
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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 |
