银或铜催化C-S键形成反应合成苯并噻嗪及芳基硫醚研究
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摘要
本论文主要围绕以下两个部分展开研究工作：(1)银催化炔烃环化反应合成含硫杂环化合物的研究；(2)铜催化Ullmann偶联反应合成芳基硫醚的研究。主要内容如下：
第一部分主要包括两方面的内容：首先在第一章中综述了近年来过渡金属催化炔烃分子内环化反应合成含氮杂环化合物的研究进展；然后在第二章中介绍了我们发现的银催化2-乙炔基苯胺衍生物和二硫化合物环化反应的结果。通过银催化2-苯乙炔基苯胺衍生物和二硫化合物的反应,合成了1,3-苯并噻嗪杂环化合物。该方法具有操作简便,条件温和及高效等优点。
第二部分主要包括三方面的内容：首先综述了合成芳基硫醚化合物的现状；然后在第三章中介绍了我们自己的工作。以铜为催化剂,芳基三甲氧基硅烷与二硫醚发生Ullmann偶联反应合成芳基硫醚化合物,该方法为从芳基二硫化合物出发合成芳基硫醚开辟了一条全新的路径；最后在第四章中介绍了铜催化吡唑二硫和芳基硼酸的Ullmann偶联反应合成一系列具有良好生物活性的氟虫腈衍生物。在上述Ullmann偶联反应中选择有机硅试剂和有机硼试剂,主要是因为它们具有低毒,良好的热稳定性,官能团能够稳定存在,以及对水和空气稳定等优点。
The dissertation includes two parts of works:(1) The synthesis of sulfur-containing heterocycles by Ag-catalyzed annulation of alkynes; (2) The synthesis of arylsulfides by copper-catalyzed Ullmann coupling reactions. The contents of this dissertation are summarized as follow:
The first part includes two contents:(1) Recent progress in intramolecular cyclization between alkynes and nitrogen atom for the synthesis of nitrogen-containing heterocycles is described in Chapter 1; (2) We introduce our results in Chapter 2 on the silver-catalyzed annulation of 2-ethynylanilines with disulfides for the synthesis of thiazines. Our method is simple, mild and efficient.
The second part includes three contents:(1) Advance in the synthesis of arylsulfides is summarized; (2) In Chapter 3, copper-catalyzed Ullmann coupling of aryltrimethoxysilanes with disulfides has been developed to prepare arylsulfides, which provides a new route to the synthesis of arylsulfides; (3) Copper-catalyzed oxidative S-arylation of 1,2-bis(o-amino-1H-pyrazolyl)disulfides with arylboronic acids for the synthesis of the potential bioactive fipronil analogues has been presented in Chapter 4. In the above Ullmann reaction, organosilanes and organoboronic acids were chosen as the reaction partners because they are low toxicity, good thermal stability, functional group compatibility and the stability in water and air.
第一部分主要包括两方面的内容：首先在第一章中综述了近年来过渡金属催化炔烃分子内环化反应合成含氮杂环化合物的研究进展；然后在第二章中介绍了我们发现的银催化2-乙炔基苯胺衍生物和二硫化合物环化反应的结果。通过银催化2-苯乙炔基苯胺衍生物和二硫化合物的反应,合成了1,3-苯并噻嗪杂环化合物。该方法具有操作简便,条件温和及高效等优点。
第二部分主要包括三方面的内容：首先综述了合成芳基硫醚化合物的现状；然后在第三章中介绍了我们自己的工作。以铜为催化剂,芳基三甲氧基硅烷与二硫醚发生Ullmann偶联反应合成芳基硫醚化合物,该方法为从芳基二硫化合物出发合成芳基硫醚开辟了一条全新的路径；最后在第四章中介绍了铜催化吡唑二硫和芳基硼酸的Ullmann偶联反应合成一系列具有良好生物活性的氟虫腈衍生物。在上述Ullmann偶联反应中选择有机硅试剂和有机硼试剂,主要是因为它们具有低毒,良好的热稳定性,官能团能够稳定存在,以及对水和空气稳定等优点。
The dissertation includes two parts of works:(1) The synthesis of sulfur-containing heterocycles by Ag-catalyzed annulation of alkynes; (2) The synthesis of arylsulfides by copper-catalyzed Ullmann coupling reactions. The contents of this dissertation are summarized as follow:
The first part includes two contents:(1) Recent progress in intramolecular cyclization between alkynes and nitrogen atom for the synthesis of nitrogen-containing heterocycles is described in Chapter 1; (2) We introduce our results in Chapter 2 on the silver-catalyzed annulation of 2-ethynylanilines with disulfides for the synthesis of thiazines. Our method is simple, mild and efficient.
The second part includes three contents:(1) Advance in the synthesis of arylsulfides is summarized; (2) In Chapter 3, copper-catalyzed Ullmann coupling of aryltrimethoxysilanes with disulfides has been developed to prepare arylsulfides, which provides a new route to the synthesis of arylsulfides; (3) Copper-catalyzed oxidative S-arylation of 1,2-bis(o-amino-1H-pyrazolyl)disulfides with arylboronic acids for the synthesis of the potential bioactive fipronil analogues has been presented in Chapter 4. In the above Ullmann reaction, organosilanes and organoboronic acids were chosen as the reaction partners because they are low toxicity, good thermal stability, functional group compatibility and the stability in water and air.
引文
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