离子液体在多组分缩合反应中的应用研究
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摘要
室温离子液体由于具有不挥发、不可燃、液态范围宽、热稳定性和化学稳定性好、溶解性好、酸碱性可调、可循环利用等优点,近年来已被作为绿色溶剂或催化剂广泛应用于有机合成领域。多组分反应具有独特的合成效率、步骤简化,结构多样性、环境友好性、原子经济性等特点,更加接近于理想合成,是一种高效的合成方法和绿色合成途径。本论文以绿色化学为理念,采用室温离子液体作催化剂或反应介质,通过多组分反应设计合成具有重要生物活性和和药理活性的杂环化合物。本论文主要研究内容如下:
首先,简要介绍了离子液体的定义、历史与现状、种类、性质及合成和多组分反应的基本概念、发展、特点及其在合成上的优势,并对近年来离子液体在多组分反应中的应用作简单综述。
其次,以廉价、简便的酸性离子液体[Hnmp]HSO4为催化剂,研究了无溶剂加热条件下,芳香醛、1,3-二羰基化合物和尿素或硫脲三组分的Biginelli缩合反应及醛、β-萘酚和环1,3-二羰基化合物的缩合反应和以乙醇为溶剂,芳香醛、乙酰乙酰苯胺、5,5-二甲基-1,3-环己二酮和乙酸铵四组分的Hantzsch缩合反应。离子液体[Hnmp]HSO4应用于这些多组分反应,避免了毒性较大的含氟离子液体和成本较高的含咪唑或丙基磺酸离子液体的使用,为四氢苯并[a]氧杂蒽-11-酮衍生物合成提供了一条高效、快捷、环境友好的新途径,扩展了Hantzsch反应适用范围,对六氢喹啉化合物库是一个重要补充。
最后,以碱性离子液体乙醇胺乙酸盐(HEAA)为催化剂、乙醇为溶剂,室温下芳香醛、4-羟基香豆素和丙二腈一锅法合成2-氨基-4-芳基-4H,5H-吡喃并[3,2-c]苯并吡喃-5-酮衍生物,该方法操作简单、反应条件温和、产率高、催化剂可以循环使用,具有很重要工业应用价值。
以上方法采用离子液体作催化剂或反应介质催化或促进多组分反应,具有操作简便、产率高、离子液体可以循环使用、对环境友好等优点,符合绿色化学要求,具有潜在的应用前景。
In recent times, room temperature ionic liquids have been widely applied in organic synthesis because of their unique properties such as non-volatility, non-inflammability, tunable acidity and alkaline, wide liquid range, good solvating ability, high chemical and thermal stability and recyclable. Multicomponent reaction is a highly efficient and green synthesis pathway, which includes excellent synthesis efficiency, simple procedure, structural diversity, environmentally friendly, atom economy and closer to the ideal synthesis. In this paper, with the view of green chemistry, a varity of heterocyclic compounds which posses important biological and pharmaceutical activities were designed and synthesized using ionic liquids as green catalyst or reaction medium through multicomponent reaction. The main contents as follow:
Firstly, the definition, development, types, properties and synthesis of ionic liquids and the conception, development, feature and the advantages in the synthesis of multicomponent reaction were introduced. And the applications of ionic liquids in multicomponent organic synthesis reactions were simply reviewed in recent years.
Secondly, Biginelli reaction of aromatic aldehydes, 1,3-dicarbonyl compounds and urea or thiourea and three-component condesation reaction of aldehydes, cyclic 1,3-dicarbonyl compounds, andβ-naphthol were investigated using inexpensive and simple acidic ionic liquid [Hnmp]HSO4 as catalyst under solvent-free conventional heating condictions, and four-component Hantzsch reaction of aldehydes, 5,5-dimethyl-1,3-cyclohexanedione, acetoacetanilide and ammonium acetate were also studied in ethanol in the presence of [Hnmp]HSO4. The applications of ionic liquid [Hnmp]HSO4 in above multicomponent reactions, which avoids the toxic fluorine containing ionic liquids and expensive imidazole or propyl sulfonic acid ionic liquids, provides an efficient, fast and environmentally friendly new procedure for the preparation of tetrahydrobenzo[a]xanthen-11-one derivatives, and extends the application scopes of Hantzsch reaction and enriches hexahydroquinoline compound libraries.
Lastly, 2-amino-4-aryl-4H,5H-pyrano[3,2-c]benzopyran-5-one derivatives were synthesized via three-component condensation reactions of aromatic aldehydes, 4-hydroxycoumarin and malononitrile in the presence of alkaline ionic liquid 2-hydroxyethylammonium acetate (HEAA) as catalyst in ethanol at room temperature. The method has several advantages such as simple operational procedure, mild reaction condition, short reaction time, high yields and the catalyst could be reused, which is much valuable in industrial applications.
Multicomponent reactions were catalyzed by ionic liquids in the above mentioned methods, which offers several advantages such as simple operational procedure, high yields, short reaction time, recyclability of the ionic liquids and environmentally friendly. These methods meet the green chemistry and have potential applications.
首先,简要介绍了离子液体的定义、历史与现状、种类、性质及合成和多组分反应的基本概念、发展、特点及其在合成上的优势,并对近年来离子液体在多组分反应中的应用作简单综述。
其次,以廉价、简便的酸性离子液体[Hnmp]HSO4为催化剂,研究了无溶剂加热条件下,芳香醛、1,3-二羰基化合物和尿素或硫脲三组分的Biginelli缩合反应及醛、β-萘酚和环1,3-二羰基化合物的缩合反应和以乙醇为溶剂,芳香醛、乙酰乙酰苯胺、5,5-二甲基-1,3-环己二酮和乙酸铵四组分的Hantzsch缩合反应。离子液体[Hnmp]HSO4应用于这些多组分反应,避免了毒性较大的含氟离子液体和成本较高的含咪唑或丙基磺酸离子液体的使用,为四氢苯并[a]氧杂蒽-11-酮衍生物合成提供了一条高效、快捷、环境友好的新途径,扩展了Hantzsch反应适用范围,对六氢喹啉化合物库是一个重要补充。
最后,以碱性离子液体乙醇胺乙酸盐(HEAA)为催化剂、乙醇为溶剂,室温下芳香醛、4-羟基香豆素和丙二腈一锅法合成2-氨基-4-芳基-4H,5H-吡喃并[3,2-c]苯并吡喃-5-酮衍生物,该方法操作简单、反应条件温和、产率高、催化剂可以循环使用,具有很重要工业应用价值。
以上方法采用离子液体作催化剂或反应介质催化或促进多组分反应,具有操作简便、产率高、离子液体可以循环使用、对环境友好等优点,符合绿色化学要求,具有潜在的应用前景。
In recent times, room temperature ionic liquids have been widely applied in organic synthesis because of their unique properties such as non-volatility, non-inflammability, tunable acidity and alkaline, wide liquid range, good solvating ability, high chemical and thermal stability and recyclable. Multicomponent reaction is a highly efficient and green synthesis pathway, which includes excellent synthesis efficiency, simple procedure, structural diversity, environmentally friendly, atom economy and closer to the ideal synthesis. In this paper, with the view of green chemistry, a varity of heterocyclic compounds which posses important biological and pharmaceutical activities were designed and synthesized using ionic liquids as green catalyst or reaction medium through multicomponent reaction. The main contents as follow:
Firstly, the definition, development, types, properties and synthesis of ionic liquids and the conception, development, feature and the advantages in the synthesis of multicomponent reaction were introduced. And the applications of ionic liquids in multicomponent organic synthesis reactions were simply reviewed in recent years.
Secondly, Biginelli reaction of aromatic aldehydes, 1,3-dicarbonyl compounds and urea or thiourea and three-component condesation reaction of aldehydes, cyclic 1,3-dicarbonyl compounds, andβ-naphthol were investigated using inexpensive and simple acidic ionic liquid [Hnmp]HSO4 as catalyst under solvent-free conventional heating condictions, and four-component Hantzsch reaction of aldehydes, 5,5-dimethyl-1,3-cyclohexanedione, acetoacetanilide and ammonium acetate were also studied in ethanol in the presence of [Hnmp]HSO4. The applications of ionic liquid [Hnmp]HSO4 in above multicomponent reactions, which avoids the toxic fluorine containing ionic liquids and expensive imidazole or propyl sulfonic acid ionic liquids, provides an efficient, fast and environmentally friendly new procedure for the preparation of tetrahydrobenzo[a]xanthen-11-one derivatives, and extends the application scopes of Hantzsch reaction and enriches hexahydroquinoline compound libraries.
Lastly, 2-amino-4-aryl-4H,5H-pyrano[3,2-c]benzopyran-5-one derivatives were synthesized via three-component condensation reactions of aromatic aldehydes, 4-hydroxycoumarin and malononitrile in the presence of alkaline ionic liquid 2-hydroxyethylammonium acetate (HEAA) as catalyst in ethanol at room temperature. The method has several advantages such as simple operational procedure, mild reaction condition, short reaction time, high yields and the catalyst could be reused, which is much valuable in industrial applications.
Multicomponent reactions were catalyzed by ionic liquids in the above mentioned methods, which offers several advantages such as simple operational procedure, high yields, short reaction time, recyclability of the ionic liquids and environmentally friendly. These methods meet the green chemistry and have potential applications.
引文
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