A Metal‐Free Three‐Component Reaction for the Regioselective Synthesis of 1, 4, 5‐Trisubstituted 1, 2, 3‐Triazoles1. Issue 38 (2nd July 2014)

• Record Type: Journal Article
• Authors: Thomas, Joice; John, Jubi; Parekh, Nikita; Dehaen, Wim
• Is Part Of: Angewandte Chemie international edition. Volume 53:Issue 38(2014)
• Page Start: 10155
• Page End: 10159
• Publication Date: 2014-07-02
• Subjects: Chemistry -- Periodicals; 540
• DOI: 10.1002/anie.201403453
• Languages: English
• ISSNs: 1433-7851

Abstract

<abstract abstract-type="main" xml:lang="en"> <title>Abstract</title> <p>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.</p> </abstract>