PEG-400介质中3-氨基联苯类、4H-苯并吡喃类和苯并吖啶类化合物的合成研究
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摘要
联苯类,以及杂环化合物中的苯并吡喃类和吖啶类化合物,具有广泛的生物活性和药理活性。这些化合物及其衍生物作为农药、医药、染料及其它精细化工产品的中间体,应用越来越广泛,世界各地科学家对它们的合成研究非常关注。
低分子量聚乙二醇PEG-400是一种常见的液体低聚物,具有低毒、可生物降解、不挥发、不可燃、价格低廉等优点;它对大多数有机及金属有机化合物溶解性能良好,在酸、碱、O_2和H_2O_2氧化体系以及NaBH_4还原体系中都很稳定,目前用PEG-400作为反应介质已开始引起人们的关注。本论文的主要工作是,以环境友好的PEG-400为反应介质,完成3-氨基-2,4-二氰基-5-甲基联苯化合物、苯并吡喃类和吖啶类化合物的合成,论文共分为四章:
第一章综述了联苯类,苯并吡喃类和吖啶类化合物的合成研究进展以及PEG-400作为反应介质在有机合成中的应用。
第二章PEG-400反应介质中,以芳香醛、丙二腈和丙酮为原料,碳酸钾做催化剂,在100℃下四组分一锅法较高产率地合成了3-氨基-2,4-二氰基-5-甲基联苯化合物。
第三章以环境友好的PEG-400为反应介质,不加任何催化剂,使芳香醛、丙二腈和5,5-二甲基-1,3-环己二酮在常温下合成了2-氨基-3-氰基-4-芳基-5-氧代-7,7-二甲基-5,6,7,8-四氢-4H-苯并吡喃类化合物;以芳香醛、丙二腈和间苯二酚为原料,在80℃下实现三组分缩合得到2-氨基-3-氰基-4-芳基-7-羟基-4H-苯并吡喃类化合物。
第四章用PEG-400作反应介质,以芳香醛、5,5-二甲基-1,3-环己二酮和α-萘胺为原料,在100℃下发生三组分缩合反应,合成了苯并[c]吖啶化合物;以芳香醛、5,5-二甲基-1,3-环己二酮和β-萘胺为原料,在100℃下实现三组分缩合,得到了苯并[a]吖啶化合物。
上述合成方法与文献报道的方法相比,具有操作简单、污染少、环境友好等优点。我们分别考察了反应介质、反应温度及时间等多种因素对上述反应的影响,从而优选出较佳反应条件。以上化合物的组成和结构经IR、~1H NMR、~(13)C NMR和Elemental Analysis得到确证。
Biaryls and heterocyclic compounds, especially 4H-pyrans and polyhydrobenzoacridine-1-one derivatives have a wide range of biological and pharmacological activities. Heterocyclic compounds and their derivatives as intermediates of pesticides, pharmaceuticals, dyes and other fine chemical products have already been widely applied. Scientists around the world very concerned about the synthesis of these compounds.
Low-molecular-weight polyethylene glycol PEG-400 is a common liquid oligomer, it is low-toxic, easily degradable, non-volatile, non-combustible and inexpensive. PEG-400 has a good solubility for most organic and metal organic compounds, moreover,which was stable in acid and alkali condition, oxidation system of O_2 and H_2O_2, redox system of NaBH4. PEG-400 as a new reaction medium has begun to attract more attention. The dissertation focuses on the synthesis of Biaryls, 4H-pyrans and polyhydrobenzoacridine-1-one derivatives using PEG-400 as reaction medium. The thesis is mainly divided into four chapters:
Chapter one: the progress of studies on the synthesis of Biaryls, 4H-pyrans and polyhydrobenzoacridine-1-one derivatives, the application of PEG-400 as reaction medium in the organic synthesis in recent years are reviewed.
Chapter two: a series of 3-Amino-2,4-dicarbonitrile-5-methylbiphenyl were synthesized by four-component condensation of aromatic aldehyde, malononitrile and acetone in PEG-400 at 100℃.
Chapter three: A various of 2-Amino-3-cyano-4-aryl-7,7-dimethyl-5-oxo-5,6,7,8-tetrahydro-4H-benzo[b]pyran were obtained by the reaction of aryl aldehydes, malononitrile and dimedone using PEG-400 as reaction medium at rt without catalyst; 2-Amino-3-cyano-7-hydroxy-4-aryl-4H-benzo-pyrans were also synthesized via three-component condensation of resorcinol, malononitrile, and various aldehydes in PEG-400 at 80 oC.
Chapter four: A series of benzo[c]acridine-1-ones and benzo[a]acridine-1-ones were synthesized by the reaction of an aldehyde,α-naphthylamine orβ-naphthylamine and dimedone in PEG-400 at 100℃.
This method has the advantages of easy work-up, less pollution and environmentally friendly procedure. We obtained the optimum reaction conditions by studing the factors respectively which affect the reactions such as the ratio of raw materials, reaction medium, temperature and time. The structures of all compounds were confirmed by IR, ~1H NMR, ~(13)C NMR and Elemental analysis.
低分子量聚乙二醇PEG-400是一种常见的液体低聚物,具有低毒、可生物降解、不挥发、不可燃、价格低廉等优点;它对大多数有机及金属有机化合物溶解性能良好,在酸、碱、O_2和H_2O_2氧化体系以及NaBH_4还原体系中都很稳定,目前用PEG-400作为反应介质已开始引起人们的关注。本论文的主要工作是,以环境友好的PEG-400为反应介质,完成3-氨基-2,4-二氰基-5-甲基联苯化合物、苯并吡喃类和吖啶类化合物的合成,论文共分为四章:
第一章综述了联苯类,苯并吡喃类和吖啶类化合物的合成研究进展以及PEG-400作为反应介质在有机合成中的应用。
第二章PEG-400反应介质中,以芳香醛、丙二腈和丙酮为原料,碳酸钾做催化剂,在100℃下四组分一锅法较高产率地合成了3-氨基-2,4-二氰基-5-甲基联苯化合物。
第三章以环境友好的PEG-400为反应介质,不加任何催化剂,使芳香醛、丙二腈和5,5-二甲基-1,3-环己二酮在常温下合成了2-氨基-3-氰基-4-芳基-5-氧代-7,7-二甲基-5,6,7,8-四氢-4H-苯并吡喃类化合物;以芳香醛、丙二腈和间苯二酚为原料,在80℃下实现三组分缩合得到2-氨基-3-氰基-4-芳基-7-羟基-4H-苯并吡喃类化合物。
第四章用PEG-400作反应介质,以芳香醛、5,5-二甲基-1,3-环己二酮和α-萘胺为原料,在100℃下发生三组分缩合反应,合成了苯并[c]吖啶化合物;以芳香醛、5,5-二甲基-1,3-环己二酮和β-萘胺为原料,在100℃下实现三组分缩合,得到了苯并[a]吖啶化合物。
上述合成方法与文献报道的方法相比,具有操作简单、污染少、环境友好等优点。我们分别考察了反应介质、反应温度及时间等多种因素对上述反应的影响,从而优选出较佳反应条件。以上化合物的组成和结构经IR、~1H NMR、~(13)C NMR和Elemental Analysis得到确证。
Biaryls and heterocyclic compounds, especially 4H-pyrans and polyhydrobenzoacridine-1-one derivatives have a wide range of biological and pharmacological activities. Heterocyclic compounds and their derivatives as intermediates of pesticides, pharmaceuticals, dyes and other fine chemical products have already been widely applied. Scientists around the world very concerned about the synthesis of these compounds.
Low-molecular-weight polyethylene glycol PEG-400 is a common liquid oligomer, it is low-toxic, easily degradable, non-volatile, non-combustible and inexpensive. PEG-400 has a good solubility for most organic and metal organic compounds, moreover,which was stable in acid and alkali condition, oxidation system of O_2 and H_2O_2, redox system of NaBH4. PEG-400 as a new reaction medium has begun to attract more attention. The dissertation focuses on the synthesis of Biaryls, 4H-pyrans and polyhydrobenzoacridine-1-one derivatives using PEG-400 as reaction medium. The thesis is mainly divided into four chapters:
Chapter one: the progress of studies on the synthesis of Biaryls, 4H-pyrans and polyhydrobenzoacridine-1-one derivatives, the application of PEG-400 as reaction medium in the organic synthesis in recent years are reviewed.
Chapter two: a series of 3-Amino-2,4-dicarbonitrile-5-methylbiphenyl were synthesized by four-component condensation of aromatic aldehyde, malononitrile and acetone in PEG-400 at 100℃.
Chapter three: A various of 2-Amino-3-cyano-4-aryl-7,7-dimethyl-5-oxo-5,6,7,8-tetrahydro-4H-benzo[b]pyran were obtained by the reaction of aryl aldehydes, malononitrile and dimedone using PEG-400 as reaction medium at rt without catalyst; 2-Amino-3-cyano-7-hydroxy-4-aryl-4H-benzo-pyrans were also synthesized via three-component condensation of resorcinol, malononitrile, and various aldehydes in PEG-400 at 80 oC.
Chapter four: A series of benzo[c]acridine-1-ones and benzo[a]acridine-1-ones were synthesized by the reaction of an aldehyde,α-naphthylamine orβ-naphthylamine and dimedone in PEG-400 at 100℃.
This method has the advantages of easy work-up, less pollution and environmentally friendly procedure. We obtained the optimum reaction conditions by studing the factors respectively which affect the reactions such as the ratio of raw materials, reaction medium, temperature and time. The structures of all compounds were confirmed by IR, ~1H NMR, ~(13)C NMR and Elemental analysis.
引文
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