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Thiolation of Pyridine-2-sulfonamides using Magnesium Thiolates
Synthesis ( IF 2.2 ) Pub Date : 2019-09-03 , DOI: 10.1055/s-0039-1690199
Benjamin Heinz , Moritz Balkenhohl , Paul Knochel

Abstract

The thiolation of pyridine-2-sulfonamides using magnesium thiolates is reported. The ortho-functionalizations of these sulfonamides using TMPMgCl·LiCl (TMP = 2,2,6,6-tetramethylpiperidyl) followed by electrophilic quenching produced a range of 3-functionalized pyridine-2-sulfonamides, which were subsequently converted into the corresponding thioethers. Finally, symmetric or asymmetric diorganodisulfides were employed as electrophiles in a one-pot ortho-functionalization–thiolation procedure, leading to pyridine 2,3-disubstituted dithioethers.

The thiolation of pyridine-2-sulfonamides using magnesium thiolates is reported. The ortho-functionalizations of these sulfonamides using TMPMgCl·LiCl (TMP = 2,2,6,6-tetramethylpiperidyl) followed by electrophilic quenching produced a range of 3-functionalized pyridine-2-sulfonamides, which were subsequently converted into the corresponding thioethers. Finally, symmetric or asymmetric diorganodisulfides were employed as electrophiles in a one-pot ortho-functionalization–thiolation procedure, leading to pyridine 2,3-disubstituted dithioethers.



中文翻译:

硫代镁盐对吡啶-2-磺酰胺的硫代反应

抽象的

据报道,使用硫醇镁将吡啶-2-磺酰胺硫醇化。的使用TMPMgCl·LiCl(TMP = 2,2,6,6-四甲基),随后加入亲电淬火这些磺酰胺-functionalizations产生的范围的3官能吡啶-2-磺酰胺,随后被转化为相应的硫醚。最后,在一个一锅的官能化-硫醇化过程中,对称或不对称的二有机二硫醚被用作亲电子试剂,从而生成吡啶2,3-二取代的二硫醚。

据报道,使用硫醇镁将吡啶-2-磺酰胺硫醇化。的使用TMPMgCl·LiCl(TMP = 2,2,6,6-四甲基),随后加入亲电淬火这些磺酰胺-functionalizations产生的范围的3官能吡啶-2-磺酰胺,随后被转化为相应的硫醚。最后,在一个一锅的官能化-硫醇化过程中,对称或不对称的二有机二硫醚被用作亲电子试剂,从而生成吡啶2,3-二取代的二硫醚。

更新日期:2019-09-03
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