噻唑啉-2-硫酮的多组分绿色合成及其在取代硫脲合成中的应用研究
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摘要
在过去的几十年时间里,多组分反应由于其独特的性质在有机合成化学中引起了广泛的关注并取得了快速的发展。为了继续开发新的多组分反应和发展环境友好的合成方法,本论文研究了噻唑啉-2-硫酮的多组分绿色合成及其在取代硫脲合成中的应用。
首先,研究建立了三组分反应合成多取代的噻唑啉-2-硫酮衍生物的绿色方法。通过胺,二硫化碳和α-溴代酮的三组分反应,一步合成了一系列多取代的噻唑啉-2-硫酮化合物。在水溶剂介导的室温条件下,各种不同取代的底物,包括胺和α-溴代酮都能与二硫化碳顺利发生三组分反应并以良好到优秀的产率得到相应的产物。
其次,研究了多取代的噻唑啉-2-硫酮化合物在取代硫脲合成中的应用。在水溶剂介导和无催化剂条件下,多种不同的胺和噻唑啉-2-硫酮都能顺利发生反应生成对应的硫脲产物,反应效率优秀。该合成方法不仅适合于合成不对称硫脲,对于对称硫脲的合成也同样适用。
总之,我们发展了一种新的多组分反应合成多取代的噻唑啉-2-硫酮杂环化合物,并对其在取代硫脲合成中的应用进行了研究。研究共合成化合物54个,其中26个为新化合物。
During the past decades, multicomponent reactions (MCRs) have attracted much attention and gained rapid development in synthetic organic chemistry due to their specific properties. In order to develop novel MCRs and environmentally benign synthesis, we have explored and established the green synthesis of thiazolidine-2-thiones by multicomponent reaction and illustrated its application in the synthesis of substituted thioureas.
Firstly, we have developed a green method for the synthesis of multisubstituted thiazolidine-2-thione derivatives via a three-component reaction of amine, carbon disulfide, and a-bromoketone in one step. By using water as the reaction medium at room temperature, various substituted substrates, including amines and a-bromoketones can react well with carbon disulfide to afford corresponding products in good to excellent yields.
Secondly, the application of thiazolidine-2-thiones in the synthesis of substituted thioureas has been investigated. By using water as the reaction medium under catalyst-free condition, a variety of amines and thiazolidine-2-thiones can react well to furnish the corresponding thiourea products in good to excellent yields. This synthetic method is suitable for the synthesis of both unsymmetrical and symmetrical thiourea derivatives.
In summary, we have devised a novel three-component reaction for the synthesis of multisubstituted thiazolidine-2-thione heterocycles and investigated its application in the synthesis of substituted thioureas. A total of 54 compounds have been synthesized in our reaserch and 26 of which have been obtained as new compounds.
首先,研究建立了三组分反应合成多取代的噻唑啉-2-硫酮衍生物的绿色方法。通过胺,二硫化碳和α-溴代酮的三组分反应,一步合成了一系列多取代的噻唑啉-2-硫酮化合物。在水溶剂介导的室温条件下,各种不同取代的底物,包括胺和α-溴代酮都能与二硫化碳顺利发生三组分反应并以良好到优秀的产率得到相应的产物。
其次,研究了多取代的噻唑啉-2-硫酮化合物在取代硫脲合成中的应用。在水溶剂介导和无催化剂条件下,多种不同的胺和噻唑啉-2-硫酮都能顺利发生反应生成对应的硫脲产物,反应效率优秀。该合成方法不仅适合于合成不对称硫脲,对于对称硫脲的合成也同样适用。
总之,我们发展了一种新的多组分反应合成多取代的噻唑啉-2-硫酮杂环化合物,并对其在取代硫脲合成中的应用进行了研究。研究共合成化合物54个,其中26个为新化合物。
During the past decades, multicomponent reactions (MCRs) have attracted much attention and gained rapid development in synthetic organic chemistry due to their specific properties. In order to develop novel MCRs and environmentally benign synthesis, we have explored and established the green synthesis of thiazolidine-2-thiones by multicomponent reaction and illustrated its application in the synthesis of substituted thioureas.
Firstly, we have developed a green method for the synthesis of multisubstituted thiazolidine-2-thione derivatives via a three-component reaction of amine, carbon disulfide, and a-bromoketone in one step. By using water as the reaction medium at room temperature, various substituted substrates, including amines and a-bromoketones can react well with carbon disulfide to afford corresponding products in good to excellent yields.
Secondly, the application of thiazolidine-2-thiones in the synthesis of substituted thioureas has been investigated. By using water as the reaction medium under catalyst-free condition, a variety of amines and thiazolidine-2-thiones can react well to furnish the corresponding thiourea products in good to excellent yields. This synthetic method is suitable for the synthesis of both unsymmetrical and symmetrical thiourea derivatives.
In summary, we have devised a novel three-component reaction for the synthesis of multisubstituted thiazolidine-2-thione heterocycles and investigated its application in the synthesis of substituted thioureas. A total of 54 compounds have been synthesized in our reaserch and 26 of which have been obtained as new compounds.
引文
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[18]3a单晶的完整数据信息收录在CCDC库中,编号为747685.
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