摘要吲哚衍生物广泛存在于天然产物中,大多数具有重要的生物活性。许多天然的或合成的吲哚化合物都被应用于药物研究领域,因此,通过有机小分子催化的串联反应合成吲哚衍生物具有重要的意义。在第一章,我们主要介绍布朗斯特酸催化的串联反应合成吲哚衍生物的研究现状。69864
在第二章,我们开发了一种有机小分子催化的方法,在无金属参与的条件下合成了一系列具有潜在药用价值的间吲哚苯胺类化合物。这个方法是消旋磷酸催化的醌亚胺缩酮与吲哚的串联1,4-加成/醇消除反应,通过机理验证,我们发现催化剂与底物形成的氢键对底物的活化具有重要作用。
在第三章,我们成功地实现了手性磷酸催化下,色胺和3-吲哚甲醇的不对称串联去芳构化反应。这个反应首次实现了3-吲哚醇的不对称串联取代反应,高收率、高立体选择性地合成了一系列含有两个手性季碳中心的吲哚并吡咯化合物。
毕业论文关键词:吲哚衍生物、布朗斯特酸、串联反应、不对称合成、加成反应
Abstract Indoles are widely distributed in nature, many of which display important biological activities. Moreover, a vast number of natural and synthetic indole compounds have found applications as pharmaceuticals. Therefore, it is of great significance to investigate the synthesis of indole derivatives by Brønsted acid-catalyzed cascade reactions. In the first chapter, will introduce the current research background on Brønsted acid-catalyzed cascade reactions for the synthesis of indole derivatives.
In the second chapter, an organocatalytic metal-free strategy has been established for the synthesis of pharmaceutically relevant meta-indolylanilines. This strategy took advantage of the reaction of indoles and quinone imine ketals (QIKs) in the presence of racemic phosphoric acid, which proceeded via a 1,4-addition/alcohol elimination reaction sequence. The control experiment demonstrated that the dual hydrogen-bonding activation mode of the catalyst to the substrates played a crucial role in the reaction.
A chiral phosphoric acid-catalyzed asymmetric cascade dearomatization reaction of tryptamines with indol-3-ylmethanols has been established. This reaction not only realized the first catalytic asymmetric cascade substitution of 3-indolylmethanols, but also provided an efficient and stereoselective method for constructing complex pyrroloindoline-based skeletons with three contiguous stereogenic centers, two of which were all-carbon quaternary centers.
Keywords: Indole derivatives, Brønsted acid, Cascade reaction, Asymmetric synthesis, Addition reaction
目录
摘要 I
Abstract II
目录 III
第一章 布朗斯特酸催化的串联反应合成吲哚衍生物的研究现状 1
1.1 布朗斯特酸催化吲哚与C=C、C=X双键的加成反应 1
1.2布朗斯特酸催化下亲核试剂进攻醇的反应 4
1.3 本论文研究的目标和内容 5
第二章 基于有机小分子催化的吲哚和醌亚胺缩酮的反应合成间吲哚苯胺衍生物 7
2.1 课题的研究背景 7
2.2 课题设想的提出 8
2.3 结果与讨论 9
2.4 反应机理的研究 13
2.5 产物的衍生化 13
2.6 总结 基于布朗斯特酸催化的串联反应来合成吲哚衍生物:http://www.751com.cn/huaxue/lunwen_78917.html