Ilkin Vladimir, Berseneva Vera, Beryozkina Tetyana, Glukhareva Tatiana, Dianova Lidia, Dehaen Wim, Seliverstova Eugenia, Bakulev Vasiliy
TOS Department, Ural Federal University named after the first President of Russia B.N. Yeltsin, 19 Mira St., 620002 Yekaterinburg, Russia.
Molecular Design and Synthesis, Department of Chemistry, KU Leuven, Celestijnenlaan 200F, 3001 Leuven, Belgium.
Beilstein J Org Chem. 2020 Dec 1;16:2937-2947. doi: 10.3762/bjoc.16.243. eCollection 2020.
-Sulfonyl amidines bearing 1,2,3-triazole, isoxazole, thiazole and pyridine substituents were successfully prepared for the first time by reactions of primary, secondary and tertiary heterocyclic thioamides with alkyl- and arylsulfonyl azides. For each type of thioamides a reliable procedure to prepare -sulfonyl amidines in good yields was found. Reactions of 1-aryl-1,2,3-triazole-4-carbothioamides with azides were shown to be accompanied with a Dimroth rearrangement to form 1-unsubstituted 5-arylamino-1,2,3-triazole-4--sulfonylcarbimidamides. 2,5-Dithiocarbamoylpyridine reacts with sulfonyl azides to form a pyridine bearing two sulfonyl amidine groups.
通过伯、仲和叔杂环硫代酰胺与烷基和芳基磺酰叠氮的反应，首次成功制备了带有1,2,3-三唑、异恶唑、噻唑和吡啶取代基的磺酰脒。对于每种硫代酰胺，都找到了一种可靠的方法来高产率地制备磺酰脒。结果表明，1-芳基-1,2,3-三唑-4-碳硫代酰胺与叠氮化物的反应伴随着Dimroth重排，形成1-未取代的5-芳基氨基-1,2,3-三唑-4-磺酰氨基甲脒。2,5-二硫代氨基甲酰吡啶与磺酰叠氮反应形成带有两个磺酰脒基团的吡啶。
