Journal
CHEMISTRY-A EUROPEAN JOURNAL
Volume 22, Issue 29, Pages 9966-9970Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.201601928
Keywords
cycloaddition; host-guest systems; metal-free; multicomponent reactions; triazoles
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Funding
- KU Leuven
- Hercules Foundation of the Flemish Government [20100225-7]
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Functionalized 1,2,3-triazole heterocycles have been known for a long time and hold an extraordinary potential in diverse research areas ranging from medicinal chemistry to material science. However, the scope of therapeutically important 1-substituted 4-acyl-1H-1,2,3-triazoles is much less explored, probably due to the lack of synthetic methodologies of good scope and practicality. Here, we describe a practical and efficient one-pot multicomponent reaction for the synthesis of a-ketotriazoles from readily available building blocks such as methyl ketones, N,N-dimethylformamide dimethyl acetal, and organic azides with 100% regioselectivity. This reaction is enabled by the in situ formation of an enaminone intermediate followed by its 1,3-dipolar cycloaddition reaction with an organic azide. We effectively utilized the developed strategy for the derivatization of various heterocycles and natural products, a protocol which is difficult or impossible to realize by other means.
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