基于铜催化炔基亚胺和重氮化合物的串联反应合成喹啉衍生物的研究
发布时间：2018-11-23 16:02
【摘要】：喹啉衍类化合物是一类重要的杂环化合物,其广泛存在于自然界中,展现出了诸多的生物活性和药理活性,如抗疟、抗肿瘤、抗炎、抗菌活性等。因此,如何高效地构筑喹啉分子一直是有机合成领域的重要研究课题。自十九世纪以来,科学家们开发了多种经典的喹啉类化合物的合成方法,如Skraup、Doebner-von Miller、Friedlander、Pfitzinger、Conrad-Limpach反应等。虽然这些方法都具有很好的应用价值,但它们仍存在诸多局限性,如反应条件苛刻,较长的反应时间,反应过程会产生大量的副产物,对环境污染的同时又对产物的分离造成困难。近些年来,过渡金属催化的串联已经成为构筑结构复杂分子的高效、简洁策略,在反应过程中,多个化学键的断裂和形成仅通过一“锅”完成。因此,开发过渡金属催化的串联反应用以合成喹啉类衍生物具有重要的研究意义。本文研究了铜催化炔基亚胺和重氮化合物的串联反应,在温和的条件下,简洁、高效地合成了一系列结构新颖的喹啉类衍生物。该反应过程涉及联烯中间体的形成,6-π电环化,1,3氢迁移。我们考察了不同催化剂、反应温度、溶剂、投料比等反应条件,得到了最佳的反应条件,即在60℃条件下,以碘化亚铜为催化剂,N,N-二甲基甲酰胺为溶剂的合成条件。并详细探索了底物的适用范围,提出了反应机理。
[Abstract]:Quinoline derivatives are an important class of heterocyclic compounds, which widely exist in nature and exhibit many biological and pharmacological activities, such as antimalarial, anti-tumor, anti-inflammatory and antibacterial activities. Therefore, how to efficiently construct quinoline molecules has been an important research topic in the field of organic synthesis. Since the nineteenth century, scientists have developed a variety of classical synthesis methods of quinoline compounds, such as Skraup,Doebner-von Miller,Friedlander,Pfitzinger,Conrad-Limpach reaction. Although these methods have good application value, but they still have many limitations, such as harsh reaction conditions, longer reaction time, reaction process will produce a large number of by-products, At the same time, it is difficult to separate the products from the environment. In recent years, the series of transition metal catalysis has become an efficient and simple strategy to construct complex molecules. In the process of reaction, the breakage and formation of multiple chemical bonds are accomplished only by a "pot". Therefore, the development of transition metal catalyzed series reaction for the synthesis of quinoline derivatives has important significance. A series of novel quinoline derivatives were synthesized succinctly and efficiently under mild conditions by copper-catalyzed series reaction of alkynyl imines with diazo compounds. The reaction involves the formation of diene intermediates, the electrocyclization of 6- 蟺, and the migration of 1 / 3 hydrogen. The optimum reaction conditions were obtained under different reaction conditions, such as reaction temperature, solvent and feed ratio. The optimum reaction conditions were obtained at 60 鈩，
本文编号：2351991
[Abstract]:Quinoline derivatives are an important class of heterocyclic compounds, which widely exist in nature and exhibit many biological and pharmacological activities, such as antimalarial, anti-tumor, anti-inflammatory and antibacterial activities. Therefore, how to efficiently construct quinoline molecules has been an important research topic in the field of organic synthesis. Since the nineteenth century, scientists have developed a variety of classical synthesis methods of quinoline compounds, such as Skraup,Doebner-von Miller,Friedlander,Pfitzinger,Conrad-Limpach reaction. Although these methods have good application value, but they still have many limitations, such as harsh reaction conditions, longer reaction time, reaction process will produce a large number of by-products, At the same time, it is difficult to separate the products from the environment. In recent years, the series of transition metal catalysis has become an efficient and simple strategy to construct complex molecules. In the process of reaction, the breakage and formation of multiple chemical bonds are accomplished only by a "pot". Therefore, the development of transition metal catalyzed series reaction for the synthesis of quinoline derivatives has important significance. A series of novel quinoline derivatives were synthesized succinctly and efficiently under mild conditions by copper-catalyzed series reaction of alkynyl imines with diazo compounds. The reaction involves the formation of diene intermediates, the electrocyclization of 6- 蟺, and the migration of 1 / 3 hydrogen. The optimum reaction conditions were obtained under different reaction conditions, such as reaction temperature, solvent and feed ratio. The optimum reaction conditions were obtained at 60 鈩，
本文编号：2351991
本文链接：https://www.wllwen.com/kejilunwen/huaxue/2351991.html
教材专著
