Synthesis of 2-arylbenzothiazoles via direct condensation between in situ generated 2-aminothiophenol from disulfide cleavage and carboxylic acids
Synthesis of 2-arylbenzothiazoles via direct condensation between in situ generated 2-aminothiophenol from disulfide cleavage and carboxylic acids
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DOI：
10.1016/j.tetlet.2017.04.078
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发表时间：
2017-06-14
影响因子：
1.8
通讯作者：
Campo, Leandra F.
中科院分区：
文献类型：
--
作者：
Coelho, Felipe L.;Campo, Leandra F.
在这项工作中，我们描述了一个简单而有效的一般方法2-芳基苯并噻唑的制备采用二硫化物和羧酸。该反应由三丁基膦促进，三丁基膦在二硫键断裂中起作用，并作为与羧酸偶联的活化剂。使用双（2-氨基苯基）二硫化物和具有给体/吸收取代基的不同羧酸研究了反应范围，这导致所需的2-芳基苯并噻唑，具有中等至良好的产率。该方法在制备淀粉样蛋白探针2-（4-氨基苯基）-6-甲氧基苯并噻唑（采用取代的双（2-氨基苯基）二硫化物）中得到了成功的验证。(C)2017爱思唯尔有限公司版权所有
In this work we describe a simple and efficient general methodology for 2-arylbenzothiazole preparation employing disulfides and carboxylic acids. The reaction is promoted by tributylphosphine that acts both in disulfide bond cleavage and as activating agent for coupling with carboxylic acids. The reaction scope was studied using bis(2-aminophenyl)disulfide and different carboxylic acids with donor/withdrawing substituents, which resulted in the desired 2-arylbenzothiazole with moderate to good yields. The method was tested with success in preparation of the amyloid probe 2-(4-aminophenyl)-6-methoxybenzothiazole that employed a substituted bis(2-aminophenyl)disulfide. (C) 2017 Elsevier Ltd. All rights reserved.