title: Metal-Free Route for the Synthesis of 4-Acyl-1,2,3-Triazoles from Readily Available Building Blocks.
abstract: 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 α-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.
authors.affiliation: Molecular Design and Synthesis, Department of Chemistry, KU Leuven, Celestijnenlaan 200F, 3001, Leuven, Belgium.
authors.forename: Joice
authors.initials: J
authors.lastname: Thomas
authors.affiliation: Molecular Design and Synthesis, Department of Chemistry, KU Leuven, Celestijnenlaan 200F, 3001, Leuven, Belgium.
authors.forename: Vince
authors.initials: V
authors.lastname: Goyvaerts
authors.affiliation: Department of Microbiology and Immunology, Rega Institute for Medical Research, KU Leuven, 3000, Leuven, Belgium.
authors.forename: Sandra
authors.initials: S
authors.lastname: Liekens
authors.affiliation: Molecular Design and Synthesis, Department of Chemistry, KU Leuven, Celestijnenlaan 200F, 3001, Leuven, Belgium. wim.dehaen@chem.kuleuven.be.
authors.forename: Wim
authors.initials: W
authors.lastname: Dehaen
keywords: cycloaddition; host-guest systems; metal-free; multicomponent reactions; triazoles