摘要：喹啉及其衍生物是重要的化工原料，在医药，染料，农药等方面都有非常必要的研究价值，2,3-二氢-4-喹啉酮在医药化学中作为一类重要的医药中间体，还可以合成出4-氨基喹啉抗疟药，这是一种新颖高效的抗疟疾药物。82095

本次论文主要分为两方面的内容，第一部分为为探究分子内胺氢化反应而进行反应底物的合成，主要为邻碘苯胺与炔丙醇在氮气保护下，在Pd2+的催化剂 作用下发生Sonogashina偶联反应，然后在苯胺的氮上引入保护基团来制备反应底物，为了探究不同取代基的影响，分别制备了含氟和含甲基的底物。

第二部分为本次论文的主要部分，探究分子内胺氢化反应，本次实验以TfOH作为反应的催化剂，先后探究了反应的条件以及催化剂的用量，确定了最佳的反应条件及用量比例，随后探究了不同取代基对反应的影响，最终结果均以较高产率获得目标产物而本次探究TfOH催化的，以邻-丙炔醇-苯胺类化合物为底物，2,3-二氢-4-喹啉酮的合成，该合成方法是一种迈耶-舒斯特重排/分子内胺氢化二者的串联反应。

毕业论文关键字：喹啉及其衍生物；2,3-二氢-4-喹啉酮；迈耶-舒斯特重排/分子内胺氢化反应；Sonogashina偶联反应；TfOH

A study on a tandem of Meyer-Schuster rearrangement / intramolecular hydroamination

Abstract: Quinoline and its derivatives are important chemical raw materials, in medicine, dyes, pesticides and other aspects have a very necessary research value, 2,3-dihydro-4-quinolinone in pharmaceutical chemistry as a class of important pharmaceutical intermediates, but also can be synthesized 4-amino quinoline antimalarial drugs, which is a new and highly effective anti-malarial drugs。

This paper is pided into two aspects, the first part of the molecular amine for the detection of hydrogenation reaction and the reaction of the substrate synthesis, mainly o-iodoan and propargyl alcohol under nitrogen protection, in the Pd2 + Catalyzed Sonogashina coupling reaction, and then the introduction of protective groups on the nitrogen of aniline to prepare the reaction substrate。 In order to explore the effect of different substituents, the fluorine-containing and methyl-containing substrates were prepared respectively。

In the second part, the main part of this paper is to explore the molecular hydrogenation of intramolecular amines。 In this experiment, TfOH was used as the catalyst for the reaction。 The reaction conditions and the amount of catalyst were investigated。 The optimum reaction conditions and dosage ratio were determined。 The effects of different substituents on the reaction were explored。 The final results were obtained in a higher yield。 The TfOH catalyzed by this study was characterized by the addition of o-propynol-aniline compounds as the substrate, 2,3- 4-quinolinone, which is a tandem reaction of both Meyer-Schuster rearrangement / intramolecular hydrogenation。

Keywords: quinoline and its derivatives; 2,3-dihydro-4-quinolinone; Meyer-Schuster rearrangement / intramolecular hydrogenation;  Sonogashira coupling reaction; TfOH

目录

第一章 绪论 1

1。1 引言 1

第二章 研究背景 3

2。1喹啉 -应用与用途 3

2。2喹啉衍生物的应用 3

2。3 喹啉酮结构的应用 3

第三章 TfOH催化的以邻-炔丙醇-苯胺为底物的串联的Meyer-Schuster反应/分子内胺氢化反应的研究 5

3。1 Meyer-Schuster重排反应