title: A metal-free three-component reaction for the regioselective synthesis of 1,4,5-trisubstituted 1,2,3-triazoles.
abstract: A metal-free three-component reaction to synthesize 1,4,5-trisubstituted 1,2,3-triazoles from readily available building blocks, such as aldehydes, nitroalkanes, and organic azides, is described. The process is enabled by an organocatalyzed Knoevenagel condensation of the formyl group with the nitro compound, which is followed by the 1,3-dipolar cycloaddition of the azide to the activated alkene. The reaction features an excellent substrate scope, and the products are obtained with high yield and regioselectivity. This method can be utilized for the synthesis of fused triazole heterocycles and materials with several triazole moieties.
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.forename: Jubi
authors.initials: J
authors.lastname: John
authors.forename: Nikita
authors.initials: N
authors.lastname: Parekh
authors.forename: Wim
authors.initials: W
authors.lastname: Dehaen
mesh_terms: D000447:Aldehydes / Q000737:chemistry*; D000473:Alkanes / Q000737:chemistry*; D001386:Azides / Q000737:chemistry*; D015394:Molecular Structure; D009574:Nitro Compounds / Q000737:chemistry*; D013237:Stereoisomerism; D014230:Triazoles / Q000138:chemical synthesis* / Q000737:chemistry
chemical_list: D000447:Aldehydes; D000473:Alkanes; D001386:Azides; D009574:Nitro Compounds; D014230:Triazoles
keywords: dipolar cycloaddition; multicomponent reactions; organocatalysis; regioselectivity; triazole