炔丙胺的自由基串联反应构建含氮环的研究
发布时间：2018-08-17 15:53
【摘要】：含氮杂环作为重要的结构单元广泛存在于天然产物、农药、医药和光电材料中,因此含氮杂环的构建已成为有机化学研究的一个重要方向。自由基串联反应在原子经济性、合成效率的高效性和环境的友好性等方面展示了突出的优点,已经成为有机合成领域至关重要的研究课题。炔丙胺是合成许多含氮杂环的有效功能前体能够合成咪唑环,吡咯环,喹啉环等各种功能含氮杂环。炔丙胺在有机合成中有着广泛的应用,它的合成方法较简单,反应条件温和,原料制备较容易,有着较多的反应位点,本论文主要关于炔丙胺的自由基串联反应来构建含氮杂环,包括以下两部分:第一部分是炔丙胺与N-碘代丁二酰亚胺的反应。常温条件下,炔丙胺与N-碘代丁二酰亚胺反应,甲醇作溶剂,生成双碘代喹啉衍生物。该反应条件温和,不需要添加其他催化剂,操作方便,这样也为构建喹啉衍生物提供了一种新型的方法。第二部分是炔丙胺与二苯基二硫醚的反应。同样以炔丙胺为原料,与二苯二硫醚在高温下发生自由基串联反应,为直接构建C-S键的提供了一种新的方法,最大程度的实现了原子经济性。
[Abstract]:Nitrogen heterocycles are widely used in natural products, pesticides, medicine and optoelectronic materials as important structural units. Therefore, the construction of nitrogen-containing heterocycles has become an important research direction in organic chemistry. Free radical series reaction has shown outstanding advantages in atom economy, high efficiency of synthesis and environmental friendliness, and has become a crucial research topic in the field of organic synthesis. Propargmine is an effective precursor for the synthesis of many nitrogen-containing heterocyclic compounds, such as imidazole ring, pyrrole ring, quinoline ring and so on. Propargyl amine has been widely used in organic synthesis. Its synthetic method is relatively simple, the reaction conditions are mild, the preparation of raw materials is easy, and it has more reaction sites. In this thesis, the radical series reaction of propargyl amine was studied to construct nitrogen-containing heterocyclic compounds, including the following two parts: the first part was the reaction of propargmine with N-iodosuccinimide. Under normal temperature, propargmine reacted with N-iodosuccinimide and methanol was used as solvent to form diiodoquinoline derivatives. The reaction conditions are mild, no other catalysts are needed, and the operation is convenient, which provides a new method for the construction of quinoline derivatives. The second part is the reaction of propargmine with diphenyl disulfide. Using propargmine as raw material, diphenyl disulfide reacted with diphenyl disulfide in series at high temperature, which provided a new method for the direct construction of C-S bond and achieved the maximum atomic economy.
【学位授予单位】：南京大学
【学位级别】：硕士
【学位授予年份】：2017
【分类号】：O626
本文编号：2188147
[Abstract]:Nitrogen heterocycles are widely used in natural products, pesticides, medicine and optoelectronic materials as important structural units. Therefore, the construction of nitrogen-containing heterocycles has become an important research direction in organic chemistry. Free radical series reaction has shown outstanding advantages in atom economy, high efficiency of synthesis and environmental friendliness, and has become a crucial research topic in the field of organic synthesis. Propargmine is an effective precursor for the synthesis of many nitrogen-containing heterocyclic compounds, such as imidazole ring, pyrrole ring, quinoline ring and so on. Propargyl amine has been widely used in organic synthesis. Its synthetic method is relatively simple, the reaction conditions are mild, the preparation of raw materials is easy, and it has more reaction sites. In this thesis, the radical series reaction of propargyl amine was studied to construct nitrogen-containing heterocyclic compounds, including the following two parts: the first part was the reaction of propargmine with N-iodosuccinimide. Under normal temperature, propargmine reacted with N-iodosuccinimide and methanol was used as solvent to form diiodoquinoline derivatives. The reaction conditions are mild, no other catalysts are needed, and the operation is convenient, which provides a new method for the construction of quinoline derivatives. The second part is the reaction of propargmine with diphenyl disulfide. Using propargmine as raw material, diphenyl disulfide reacted with diphenyl disulfide in series at high temperature, which provided a new method for the direct construction of C-S bond and achieved the maximum atomic economy.
【学位授予单位】：南京大学
【学位级别】：硕士
【学位授予年份】：2017
【分类号】：O626
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