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摘要：香豆素是一类重要的化合物，包括天然香豆素和合成香豆素，具有抗病毒、抗癌、抗微生物、抗炎症等各方面的生物活性。本课题所研究合成的一系列双香豆素和呋喃香豆素衍生物，具有潜在的生物活性和药用活性，同时在构建新型活性骨架，合成有应用价值的化合物，充实新的活性化合物库方面显示出独特的优点。此外，所设计的多组分反应可以使起始原料最大限度地转化为目标产物，避免中间体的分离而带来的资源浪费，充分体现了原子经济性和环境友好性。3,3'-次甲基-双(4-氨基-香豆素)衍生物是以4-羟基香豆素为原料，经过取代、缩合反应制备。2-(2-氧-2H-苯并吡喃-3-羰基)-2H-呋喃[3,2-c]香豆素衍生物是以邻羟基苯甲醛为原料，经过Robinson增环、卤取代、季铵化、缩合反应制备。通过工艺条件对照实验，本文优化了这几步反应的实验过程，增强了各步反应的稳定性和重复性，提高了产物收率和纯度，降低了实验成本，为今后的实际应用摸索出了一条相对可行的工艺路线。27824
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毕业论文关键词：香豆素衍生物；多组分反应；3,3'-次甲基-双(4-氨基-香豆素)衍生物；2-(2-氧-2H-苯并吡喃-3-羰基)-2H-呋喃[3,2-c]香豆素衍生物；合成
Study on Synthesis of Coumarin Derivatives by Multicomponent Reactions
Abstract: Coumarins are important class of compounds including natural products and synthetic products. They have many excellent biological activities in anti-virus, anti-cancer, anti-microbe and anti-inflammatory. The dicoumarin and furanocoumarin derivatives prepared in this paper not only have potential biological and medicinal activities, but also show unique advantages in constructing new molecular skeleton and synthesizing valuable compounds. In addition, by multicomponent reactions, the starting materials are furthest converted to the target products without waste of resources. This fully embodies atomic economy and environmental friendliness. 3,3'-Methenyl-bis(4-amine-coumarin) derivatives are synthesized by substitution reaction and condensation reaction steps based on 4-hydroxycoumarin as the starting material. 2-(2-Oxo-2H-benzopyran-3-carbonyl)-2H-furan[3,2-c] coumarin derivatives
are synthesized by Robinson annulation reaction, halogen substitution reaction, quaternization reaction and condensation reaction steps based on 2-hydroxybenzaldehyde as the starting material. Through the contrast experiment, we optimize experiment condition, enhance stability and reproducibility of each reaction, improve the productivity and purity of product, reduce production cost and determine a relatively feasible process which can be applied for major industrial production in the future.
Key Words: Coumarin derivatives; Multicomponent reactions; 3,3'-Methenyl-bis(4-amine-cou
marin) derivatives; 2-(2-Oxo-2H-benzopyran-3-carbonyl)-2H-furan[3,2-c]coumarin derivatives; Synthesis
目 录
1 前言 1
1.1 香豆素及其衍生物简介 1
1.2 呋喃类香豆素简介 1
1.3 多组分反应 2
1.3.1 多组分反应简介 2
1.3.2 多组分反应在香豆素衍生物合成中的应用 3
2 文献综述与方案论证 9
2.1 文献综述 9
2.1.1 Perkin反应合成法 9
2.1.2 Wittig反应合成法 9
2.1.3 Pechmann反应合成法 10
2.1.4 Kneovenagel反应合成法 10
2.1.5 Ponndorf反应合成法 11
2.1.6 Houben-Hoesch反应合成法 11