Institute of Chemistry, Saint Petersburg State University, 26 Universitetsky prospekt, Peterhof 198504, Russia.
J Org Chem. 2021 Dec 3;86(23):17516-17522. doi: 10.1021/acs.joc.1c02309. Epub 2021 Nov 19.
A three-component synthesis of 1,5-disubstituted 1,2,3-triazoles from α-acetyl-α-diazomethane sulfonamides, primary aliphatic amines, and aromatic aldehydes is presented. The 1,2,3-triazoles can be accessed in two alternative variants, depending on the substitutions in the sulfonamide portion of the diazo reagent. In one variant, intermediate 1,2,3-triazoline-4-sulfonamides are isolated chromatographically and then subjected to thermally promoted aromatization with elimination of sulfur(IV) oxide and amine. In the other variant, both chemical transformations take place in a single step conducted at room temperature.
本文介绍了一种从α-乙酰基-α-重氮甲烷磺酰胺、伯脂肪胺和芳香醛合成 1,5-二取代 1,2,3-三唑的三组分方法。根据重氮试剂磺酰胺部分的取代基，1,2,3-三唑可以通过两种替代变体来获得。在一种变体中，通过色谱法分离得到中间 1,2,3-三唑啉-4-磺酰胺，然后在热促进下进行消除二氧化硫和胺的芳香化反应。在另一种变体中，这两个化学转化在室温下进行的单步反应中同时发生。
