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。的邻使用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,在一个一锅的邻官能化-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。的邻使用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,在一个一锅的邻官能化-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。