聚乙二醇（PEG）作为绿色反应介质的若干有机反应研究
摘要
绿色化学已经成为21世纪学术领域和工业研究的中心话题,发展对环境友好、清洁的合成方法成是当今有机化学的目标之一,开发无毒无害的有机合成溶剂越来越引起大家的关注。
聚乙二醇(PEG)和它的单甲醚化合物是一类价廉、热稳定性高、可循环使用、具备相转移性能并且无毒的介质。PEG在生物学上广泛应用于药物释放和生物偶合的诊断型工作,虽然目前不是一种广泛应用的溶剂介质,但是也有一些成功应用于各种各类化学反应的实例。本论文主要围绕以聚乙二醇为溶剂介质的绿色有机合成反应展开研究,主要内容和结果如下：
1、研究了以PEG为介质的N-取代亚胺类化合物合成方法。亚胺类化合物是一种广泛应用于生物医药、合成化学和聚合物化学的重要化合物。本文采用两种方法合成该类化合物,一种是丁二酸酐、邻苯二甲酸酐和胺类的直接缩合,另一种是通过亚胺类杂环化合物和卤代物反应得到。两种方法都取得了较好的结果：具有反应时间短、产率高和操作简便等优点,聚乙二醇可以循环使用而不影响反应的效果。
2、发明了一种以PEG为介质的酰胺直接合成法。本文研究了用芳香醛和芳香胺、脂肪胺在氧化剂条件下合成相应的酰胺类化合物的方法,筛选了多种氧化剂,最终选择了PEG-次氯酸钠和硫酸叔丁基氢铵这种氧化体系,使用该体系进行反应的结果较好,反应条件温和,易于操作,产率可观。
3、研究了以PEG为介质的1,4-二氢吡啶类衍生物的合成方法。1,4-二氢吡啶类衍生物是应用于生物学和医学上的重要化合物,是制备多种药物的中间体。本文采用经典的三组分在PEG介质中进行Hantzsch反应,无需其他任何催化剂,反应的结果非常好,产率极高,易操作且PEG可以循环使用。
4、研究了以PEG为介质的经典Michael加成反应合成p-胺基羰基、氰基化合物的方法,这两类化合物具有广泛的生物与药用活性。本文以PEG-400为反应介质,由苄胺、脂肪胺和芳香胺对α,β-不饱和羰基化合物、氰基化合物在室温下进行碳氮键的Michael加成。该方法的突出优点为：PEG作为相转移性溶剂既经济安全且环保可循环使用,反应条件温和,产率高。
Green chemistry is becoming a central issue in both academic and industrial research in the21st century, and the development of environmentally benign and clean synthetic procedures has become the goal of present day organic synthesis. Organic reactions without the use of harmful organic solvents are now of great interest in organic synthesis.
PEG and its monomethyl ethers are inexpensive, thermally stable, recoverable, and nontoxic media for phase-transfer catalysts. PEG, a biologically acceptable polymer used extensively in drug delivery and in bioconjugates as tool for diagnostics, has hitherto not been widely used as a solvent medium but has been used as a support for various transformations. In this dissertation, we studied the green organic reaction by using PEG as the solvent medium, the content and results of the research as following:
1. The synthesis of N-substituted imide by using PEG as the solvent medium. Imide derivatives are compounds of considerable interest due to their biological properties and their interest as intermediates in synthesis and in polymer chemistry. Two procedures were used to synthesis these imides:one is the directive condensation by the reactions of succinic anhydrides or phthalic anhydrides with amines;the other one is the substitution by the reaction of nitrogen heterocycles with halides, and both methods were easy-worked with excellent yields and short reaction times respectively, and PEG could be recyclable.
2. A directly synthetic method of amides was explored. Amide derivatives are important compounds in organic synthesis and medical industry. They were obtained by directly oxidative of aromatic aldehydes with aromatic amines or aliphatic amines. The best oxidant system (PEG-NaOCl/Bu4NHSO4) was selected from several oxidant systems, the results of the reactions could get considerable yields, the reaction condition was mild and easy to work.
3.1,4-Dihydropyridine derivatives exhibit a large range of biological activities. We explored a protocol by using Hantzsch condensation of ethyl (methyl) acetoacetate and aromatic aldehydes in PEG-400with ammonium acetate, this reaction needed not any other catalyst. The results were really excellent, high yields, PEG was recyclable.
4. We developed an efficient and green approach to β-amino carbonyl and nitrile compounds which have attracted considerable attention in organic synthesis as to their wide range of biological activities and pharmacological properties. Room temperature Michael additions of various aliphatic and aromatic amines to α, β-unsaturated esters and acrylonitrile to form C-N bond in PEG-400which as a phase transfer solvent was economic, safe, and environment-friendly. Simple experimental procedure, mildness of the conversion, high yields, recyclable.
聚乙二醇(PEG)和它的单甲醚化合物是一类价廉、热稳定性高、可循环使用、具备相转移性能并且无毒的介质。PEG在生物学上广泛应用于药物释放和生物偶合的诊断型工作,虽然目前不是一种广泛应用的溶剂介质,但是也有一些成功应用于各种各类化学反应的实例。本论文主要围绕以聚乙二醇为溶剂介质的绿色有机合成反应展开研究,主要内容和结果如下：
1、研究了以PEG为介质的N-取代亚胺类化合物合成方法。亚胺类化合物是一种广泛应用于生物医药、合成化学和聚合物化学的重要化合物。本文采用两种方法合成该类化合物,一种是丁二酸酐、邻苯二甲酸酐和胺类的直接缩合,另一种是通过亚胺类杂环化合物和卤代物反应得到。两种方法都取得了较好的结果：具有反应时间短、产率高和操作简便等优点,聚乙二醇可以循环使用而不影响反应的效果。
2、发明了一种以PEG为介质的酰胺直接合成法。本文研究了用芳香醛和芳香胺、脂肪胺在氧化剂条件下合成相应的酰胺类化合物的方法,筛选了多种氧化剂,最终选择了PEG-次氯酸钠和硫酸叔丁基氢铵这种氧化体系,使用该体系进行反应的结果较好,反应条件温和,易于操作,产率可观。
3、研究了以PEG为介质的1,4-二氢吡啶类衍生物的合成方法。1,4-二氢吡啶类衍生物是应用于生物学和医学上的重要化合物,是制备多种药物的中间体。本文采用经典的三组分在PEG介质中进行Hantzsch反应,无需其他任何催化剂,反应的结果非常好,产率极高,易操作且PEG可以循环使用。
4、研究了以PEG为介质的经典Michael加成反应合成p-胺基羰基、氰基化合物的方法,这两类化合物具有广泛的生物与药用活性。本文以PEG-400为反应介质,由苄胺、脂肪胺和芳香胺对α,β-不饱和羰基化合物、氰基化合物在室温下进行碳氮键的Michael加成。该方法的突出优点为：PEG作为相转移性溶剂既经济安全且环保可循环使用,反应条件温和,产率高。
Green chemistry is becoming a central issue in both academic and industrial research in the21st century, and the development of environmentally benign and clean synthetic procedures has become the goal of present day organic synthesis. Organic reactions without the use of harmful organic solvents are now of great interest in organic synthesis.
PEG and its monomethyl ethers are inexpensive, thermally stable, recoverable, and nontoxic media for phase-transfer catalysts. PEG, a biologically acceptable polymer used extensively in drug delivery and in bioconjugates as tool for diagnostics, has hitherto not been widely used as a solvent medium but has been used as a support for various transformations. In this dissertation, we studied the green organic reaction by using PEG as the solvent medium, the content and results of the research as following:
1. The synthesis of N-substituted imide by using PEG as the solvent medium. Imide derivatives are compounds of considerable interest due to their biological properties and their interest as intermediates in synthesis and in polymer chemistry. Two procedures were used to synthesis these imides:one is the directive condensation by the reactions of succinic anhydrides or phthalic anhydrides with amines;the other one is the substitution by the reaction of nitrogen heterocycles with halides, and both methods were easy-worked with excellent yields and short reaction times respectively, and PEG could be recyclable.
2. A directly synthetic method of amides was explored. Amide derivatives are important compounds in organic synthesis and medical industry. They were obtained by directly oxidative of aromatic aldehydes with aromatic amines or aliphatic amines. The best oxidant system (PEG-NaOCl/Bu4NHSO4) was selected from several oxidant systems, the results of the reactions could get considerable yields, the reaction condition was mild and easy to work.
3.1,4-Dihydropyridine derivatives exhibit a large range of biological activities. We explored a protocol by using Hantzsch condensation of ethyl (methyl) acetoacetate and aromatic aldehydes in PEG-400with ammonium acetate, this reaction needed not any other catalyst. The results were really excellent, high yields, PEG was recyclable.
4. We developed an efficient and green approach to β-amino carbonyl and nitrile compounds which have attracted considerable attention in organic synthesis as to their wide range of biological activities and pharmacological properties. Room temperature Michael additions of various aliphatic and aromatic amines to α, β-unsaturated esters and acrylonitrile to form C-N bond in PEG-400which as a phase transfer solvent was economic, safe, and environment-friendly. Simple experimental procedure, mildness of the conversion, high yields, recyclable.
引文
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