炔胺Meyer-Schuster反应的研究
毕业论文关键词：Meyer-Schuster 重排，含氮杂环化合物，4-喹啉酮
Research on Meyer - Schuster reaction of alkynylamines
Abstract : The heterocyclic compounds containing nitrogen can easily be modified and can be easily introduced into functional groups.The study of the synthesis of nitrogen heterocyclic compounds has always been a hot spot in organic chemistry research.4-quinolone is a kind of important pharmaceutical intermediates and to it as raw material can synthesize a variety of quinolone compounds, such as norfloxacin and ciprofloxacin.The research direction of this thesis is 1-Methanesulfonyl-2,3dihydro-1H-quinolin-4-one and 1-(4-Methoxy-benzenesulfonyl)-2,3dihydro-1H-quinolin-4-one by Meyer-Schuster rearrangement reaction.In this paper, we take the aniline and propylene glycol as the raw materials, with PdCl2(PPh3)2 and Et3N as catalysts, get 3-(2-Amino-phenyl)-prop-2-yn-1-ol(1); The methyl sulfonyl chloride or methoxy benzene sulfonyl chloride, by using pyridine and anhydrous dichloromethane as catalyst, get N-[2-(3-Hydroxy-prop-1-ynyl)-phenyl]-methanesulfonamide or N-[2-(3-Hydroxy-prop-1-ynyl)-phenyl]-4-methoxy-benzenesulfonamide (2); Three fluoride and toluene as raw material, three fluorine methyl sulfonic acid as the catalyst, get 1-Methanesulfonyl-2,3dihydro-1H-quinolin-4-one or 1-(4-Methoxy-benzenesulfonyl)-2,3dihydro-1H-quinolin-4-one. Its structure was determined by NMR and IR spectra.
KeyWords : Meyer-Schuster rearrangement，Nitrogenous heterocyclic compounds, 4- quinolones
目 录
1 概述 1
1.1 杂环化合物 1
1.1.1 含氮杂环化合物 1
1.1.2 喹啉酮 2
1.2 实验方法及原理 4
1.2.1 Meyer-Schuster重排反应机理 4
1.2.2 薄层色谱法 7
1.2.3 柱层析 8
1.2.4 红外光谱 9
1.2.5 核磁共振氢谱 11
2 实验部分 13
2.1 试剂及仪器 13
2.1.1 实验试剂 13
2.1.2 实验仪器 13
2.3 实验内容 14
2.3.1 催化剂Pd(PPh3)2Cl2 的合成 14
2.3.2 MS（1-甲基磺酰基-2,3-二氢-4-喹啉酮）的合成 14
2.3.3 MbS（1-对甲氧基苯磺酰基-2,3-二氢-4-喹啉酮）的合成 16
3 实验结果与讨论 17
4 总结 18
致谢 19
参考文献 20
附录 21
1 概述
1.1 杂环化合物
有机化学是开始于研究天然产物的。长久以来，具备了强烈的生物活性的天然的有机化合物，一直都是有机化学研究中的关注点。而这一些天然的具有活性的化合物,很大部分都是杂环化合物。比如，核酸分子有:核糖、磷酸和碱基，三个部分组成的。核糖也是以杂环形式存在的。植物中存在的生物碱大部分都归属于杂环化合物,如奎宁碱、颠茄碱、吗啡碱等等,这些的药用价值都很显著。
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