基于靛红参与的吡唑螺氧化吲哚衍生物洁净合成研究

发布时间：2018-02-04 20:48

  本文关键词： 螺环化合物 靛红 多组分反应 醋酸 水　出处：《江苏师范大学》2017年硕士论文　论文类型：学位论文

【摘要】：本文以多组分反应为基础合成出多系列的靛红螺氧化吲哚化合物,反应原料易得、价格低廉、反应操作简便。本文研究的多组分反应均是在水里面完成的反应,它们是合成具有分子多样性的化合物有效途径,本研究具有反应聚合性,原子经济性和环境友好的优点。第一章主要介绍了多组分反应的涵义、历史及其优点,合成螺环化合物的意义和应用前景,介绍了以靛红为基础原料在其3位合成各种螺环化合物的研究进展,简述了近几年在水相中的有机合成的研究。第二章研究了以3-氨基-1-苯基-1H-吡唑-5(4H)-酮、靛红及(取代)二苯乙酮为底物,以醋酸为催化剂,水作为溶剂,简单高效的合成出一系列的吡唑并吡啶螺氧化吲哚衍生物。避免了使用有机溶剂,符合“绿色化学”的概念。第三章研究了在水中以茚酮及萘酮、靛红和3-氨基-1-苯基-1H-吡唑-5(4H)-酮为原料用醋酸催化一锅法合成茚并杂环及苯并喹啉螺氧化吲哚衍生物,进一步丰富了茚并杂环及喹啉化合物库。第四章研究了以水作为溶剂,在醋酸的催化下,以靛红、3-氨基-1-苯基-1H-吡唑-5(4H)-酮和单环酮或杂环酮为原料合成了一系列含吡唑环的螺氧化吲哚衍生物,反应条件温和,操作简单,产率高。第五章研究了以靛红、氨基吡唑类化合物和β-环二酮为起始原料,以水为溶剂在醋酸的催化下一锅法合成出了吡唑并喹啉及吡唑并吡啶螺氧化吲哚化合物,该反应提供了一条快速、简便、经济、环保的合成途径。所有产物结构均经过核磁共振氢谱和碳谱、红外光谱、高分辨质谱表征,并对这些化合物的合成提出了可能的反应机理。实验研究表明,在水相中的多组分反应合成吲哚螺环化合物是一条重要的途径,而靛红则是合成螺环化合物的重要试剂。本研究具有原子经济性高、无毒性、环境友好、条件温和、产率高等优点。
[Abstract]:On the basis of multicomponent reaction, a series of indole compounds were synthesized. The raw materials are easy to get, the price is low and the reaction is easy to operate. The multicomponent reactions studied in this paper are all completed in water. They are effective ways to synthesize compounds with molecular diversity. This study has the advantages of reactive polymerization, atomic economy and environmental friendliness. Chapter 1 mainly introduces the meaning, history and advantages of multicomponent reactions. The significance and application prospect of the synthesis of spirocyclic compounds are reviewed. The research progress in the synthesis of various spirocyclic compounds based on indirubin at its 3 position is introduced. The study of organic synthesis in aqueous phase in recent years is reviewed. In chapter 2, 3Amino-1-phenyl-1H-pyrazole-4Hoxone, indirubin and (substituted) diacetophenone are used as substrates. Using acetic acid as catalyst and water as solvent, a series of pyrazolopyridine spiroxide indole derivatives were synthesized in a simple and efficient way, avoiding the use of organic solvents. In accordance with the concept of "green chemistry". In chapter 3, indene and naphthone in water were studied. Indolein and 3-amino-1-phenyl-1-H-pyrazolone were used as raw materials to synthesize indolein and benzoquinoline spirooxidated indole derivatives in one pot with acetic acid. In chapter 4th, water was used as solvent, and indirubin was used as catalyst under the catalysis of acetic acid. A series of spiroxyindole derivatives containing pyrazole ring were synthesized from 3-amino-1-phenyl -1H-pyrazole-4Hzolidone and monocyclic ketones or heterocyclic ketones. The reaction conditions were mild and the operation was simple. In chapter 5th, the raw materials of indirubin, aminopyrazole and 尾 -cyclodione were studied. Pyrazolyl quinoline and pyrazopyridine spiroxide indoles were synthesized by one-pot method in the presence of acetic acid with water as solvent. The reaction provides a rapid, simple and economical reaction. All the products were characterized by nuclear magnetic resonance (NMR) and carbon spectroscopy (NMR), infrared spectroscopy (IR) and high resolution mass spectrometry (HRMS). The possible reaction mechanism of these compounds was proposed. The synthesis of indole spirocyclic compounds by multicomponent reaction in aqueous phase is an important way, while indirubin is an important reagent for the synthesis of spirocyclic compounds. This study is characterized by high atomic economy, non-toxicity and environmental friendliness. Mild conditions, high yield and other advantages.
【学位授予单位】：江苏师范大学
【学位级别】：硕士
【学位授予年份】：2017
【分类号】：O626
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本文编号：1491104