ORGN 366 |
| In recent years, ynamides chemistry has emerged as a field of interest for the development of new synthetic methodologies. Here, we report a tandem azidination-[3 + 2] cycloaddition of ynamides to synthesize chiral ynamide substituted triazoles, which will be potentially useful in both material chemistry and medicinal chemistry. Vinyl or aryl azides were in situ generated through a Cu(I)-L-proline coupling of vinyl or aryl iodides with sodium azide, then terminal ynamides in DMSO solution were added by syringe pump to the system to initiate a Cu(I)-catalyzed ligation reaction of organic azides (without separation) and terminal ynamides; triazoles adduct were achieved in good to excellent yields. A tandem hydroazidination-[3 + 2] cycloaddition reactions were also studied. By using allyl iodide to trap the Cu(I) acetylide generated in click chemistry, we can generated triazole tethered dienes, which can be transformed to medium-sized fused triazoles in good yields.
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New Reactions and Methodology
8:00 AM-12:00 PM, Tuesday, 12 September 2006 Moscone Center -- Room 133, Oral
Division of Organic Chemistry |
