31794-11-3Relevant articles and documents
Metal-Free Synthesis of Functional 1-Substituted-1,2,3-Triazoles from Ethenesulfonyl Fluoride and Organic Azides
Giel, Marie-Claire,Smedley, Christopher J.,Mackie, Emily R. R.,Guo, Taijie,Dong, Jiajia,Soares da Costa, Tatiana P.,Moses, John E.
supporting information, p. 1181 - 1186 (2019/12/11)
The boom in growth of 1,4-disubstituted triazole products, in particular, since the early 2000’s, can be largely attributed to the birth of click chemistry and the discovery of the CuI-catalyzed azide–alkyne cycloaddition (CuAAC). Yet the synthesis of relatively simple, albeit important, 1-substituted-1,2,3-triazoles has been surprisingly more challenging. Reported here is a straightforward and scalable click-inspired protocol for the synthesis of 1-substituted-1,2,3-triazoles from organic azides and the bench stable acetylene surrogate ethenesulfonyl fluoride (ESF). The new transformation tolerates a wide selection of substrates and proceeds smoothly under metal-free conditions to give the products in excellent yield. Under controlled acidic conditions, the 1-substituted-1,2,3-triazole products undergo a Michael addition reaction with a second equivalent of ESF to give the unprecedented 1-substituted triazolium sulfonyl fluoride salts.
1 H - 1, 2, 3 - triazole preparation method (by machine translation)
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Paragraph 0039; 0042; 0043; 0053; 0056; 0057, (2019/02/03)
The invention belongs to the field of fine chemical pharmaceutical intermediates, discloses a 1 H - 1, 2, 3 - triazole of the preparation method. The method to replace the halogen animal pen and sodium azide in fat alcohol and water in the mixed solvent of azide, after being extracted by the organic solvent, directly with the acetylene in a pressure reactor in the reaction process for preparing the intermediate, then separating out intermediate, obtained through the strong acid debenzylation 1 H - 1, 2, 3 - triazole, through the rectification is purified to high purity of 1 H - 1, 2, 3 - triazole finished product. The whole synthetic route of the raw materials are cheap and easy to obtain, the process of synthesis of few, simple operation, low operation cost, process and environmental protection, it is very suitable for industrial production, has a very high industrial application value. (by machine translation)
Phase-Vanishing Method with Acetylene Evolution and Its Utilization in Several Organic Syntheses
Matake, Ryosuke,Niwa, Yuki,Matsubara, Hiroshi
supporting information, p. 2354 - 2357 (2015/06/02)
A novel quadraphasic phase-vanishing system in which acetylene is evolved from calcium carbide and directly applied in situ to the Sonogashira coupling reaction was developed. This method, which provides a safe, convenient, and one-pot means to utilize gaseous reagents without special equipment, was also applied to a Cu-catalyzed azide-alkyne cycloaddition (CuAAC) reaction and a three-component aldehyde-alkyne-amine (A3) coupling reaction with excellent results. (Figure Presented).
