铜催化串联环化合成含三氟甲基喹啉衍生物

发布时间：2018-03-05 09:59

本文选题：喹啉　切入点：三氟甲基　出处：《江西师范大学》2016年硕士论文　论文类型：学位论文

【摘要】：喹啉是一类具有生物活性的天然产物,由于其结构的特殊性,被广泛应用于药物分子的合成。含有三氟甲基的喹啉化合物尤为引人关注,因为在有机物中引入的氟原子往往在物理、化学、生物活性中发挥关键作用。由于这类化合物的重要性,尽管已经有高效合成含三氟甲基喹啉化合物的方法被报道,然而,高效合成含三氟甲基喹啉类药物的方法仍至关重要,因为已被报道的方法依然存在一些缺陷如:苛刻的反应条件和需要昂贵的催化剂等。因此,在温和的条件下,发展一种实用的方法合成含三氟甲基喹啉化合物是有必要的。本文主要包括以下三个部分:1、简单介绍了近期使用三氟甲基砌块和氟化试剂构建含三氟甲基化合物的研究进展。2、利用含氟砌块法发展了以N-(2-烯基芳基)烯胺为底物,以空气作氧化剂,CuCl2作催化剂的条件下发生氧化/环化,合成2-三氟甲基喹啉衍生物的方法。该方法新颖且高效,具有良好的底物适用性。我们还可以通过控制反应条件,选择性地合成含4-烷基或4位无取代的2-三氟甲基喹啉化合物。3、发展了N-邻乙炔基苯基烯胺在以Togni’s试剂为三氟甲基源,Cu2O为催化剂,3当量的吡啶作为碱的条件下,成功合成了4-(2’,2’,2’-三氟)乙基的喹啉衍生物,该反应能以中等至良好的收率得到一系列目标产物。基于前期报道和验证实验,我们认为它可能是先经过三氟甲基自由基加成,之后再环化,最终合成目标产物的反应路径。
[Abstract]:Quinoline is a kind of natural products with biological activity. Because of its special structure, quinoline is widely used in the synthesis of drug molecules, especially quinoline compounds containing trifluoromethyl. Because fluorine atoms introduced into organic compounds often play a key role in physical, chemical and biological activities. Because of the importance of these compounds, although highly efficient synthesis of trifluoromethyl quinoline compounds has been reported, The efficient synthesis of trifluoromethyl quinolines remains critical because the reported methods still have some shortcomings such as harsh reaction conditions and the need for expensive catalysts. It is necessary to develop a practical method for the synthesis of trifluoromethyl quinoline compounds. This paper mainly consists of three parts: 1, and briefly introduces the recent construction of trifluoromethyl compounds using trifluoromethyl block and fluorination reagent. In this paper, we have developed a new method of fluorine-containing block method, which is based on N-butadiene aryl) enylamine, The synthesis of 2-trifluoromethylquinoline derivatives by oxidation / cyclization with air as oxidant and CuCl _ 2 as catalyst is novel, efficient and suitable for substrates. We can also control the reaction conditions. The selective synthesis of 2-trifluoromethylquinoline compound containing 4-alkyl or 4-position unsubstituted 2,3-trifluoromethyl quinoline compound. N- o-acetylphenyl enylamine was developed under the condition that pyridine with Togni's reagent as the catalyst of trifluoromethyl source Cu2O as the base, A series of target products have been successfully synthesized by the synthesis of the quinoline derivatives of 4-H2H2O2O2-TIFOXYL) ethyl with moderate to good yield. Based on previous reports and validation experiments, we believe that it may first be added by trifluoromethyl radical. The reaction path of the target product is finally synthesized by cyclization.
【学位授予单位】：江西师范大学
【学位级别】：硕士
【学位授予年份】：2016
【分类号】：O626

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