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Regioselective synthesis of heterocyclic N-sulfonyl amidines from heteroaromatic thioamides and sulfonyl azides
Beilstein Journal of Organic Chemistry ( IF 2.7 ) Pub Date : 2020-12-01 , DOI: 10.3762/bjoc.16.243
Vladimir Ilkin , Vera Berseneva , Tetyana Beryozkina , Tatiana Glukhareva , Lidia Dianova , Wim Dehaen , Eugenia Seliverstova , Vasiliy Bakulev

N-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 N-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-N-sulfonylcarbimidamides. 2,5-Dithiocarbamoylpyridine reacts with sulfonyl azides to form a pyridine bearing two sulfonyl amidine groups.

中文翻译:

由杂芳族硫代酰胺和磺酰基叠氮化物区域选择性合成杂环N-磺酰基am

带有1,2,3-三唑,异恶唑,噻唑和吡啶取代基的N-磺酰am是通过伯,仲和叔杂环硫代酰胺与烷基和芳基磺酰基叠氮化物的反应首次成功制备的。对于每种类型的硫酰胺,都发现了以高收率制备N-磺酰基am的可靠方法。1-芳基-1,2,3-三唑-4-碳硫酰胺与叠氮化物的反应显示伴随Dimroth重排形成1-未取代的5-芳基氨基-1,2,3-三唑-4- N-磺酰基碳亚胺。2,5-二硫代氨基甲酰基吡啶与磺酰基叠氮化物反应形成带有两个磺酰基am基的吡啶。
更新日期:2020-12-01
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