超声辐射下3-取代吲哚衍生物的合成与结构表征
摘要
吲哚化学的研究已经并仍将是杂环化学中最活跃的领域之一,特别是3-取代吲哚衍生物,已用于许多天然产物和相应具有生物活性化合物重要骨架的构筑,其合成方法的研究格外令人注目,近几年来,由吲哚一步合成3-取代吲哚衍生物的报道剧增。本文按合成过程中所用催化剂的种类,综述近几年来由吲哚为原料合成二吲哚甲烷、β-吲哚酮、β-吲哚醇、β-吲哚硝基化合物等3-取代吲哚衍生物的研究进展。
超声辐射技术在有机合成中的应用研究近二十年来发展非常迅速,与传统的有机合成方法比较,操作方便,反应条件温和,缩短反应时间,提高反应产率。论文介绍超声波的作用原理,综述近几年来超声波在有机合成中的一些应用。
超声辐射下吲哚与1,5-二芳基-1,4-戊二烯-3-酮分别在三氯化铝、碘、对甲苯磺酸等三种不同催化剂催化下的共轭加成反应。考察了超声辐射频率、反应溶剂、底物与催化剂的摩尔比、加料顺序等对反应的影响,推测了可能的反应机理。
以钨硅酸(SiO2·12WO3·24H2O)为催化剂,将吲哚与芳香醛或芳香酮在超声辐射下反应15-120 min,二吲哚甲烷的收率53-97%。与搅拌方法相比,反应时间缩短,反应收率高。与芳香醛相比,芳香酮的反应活性明显降低。
超声辐射能够有效促进无水氯化锌催化的吲哚与芳叉丙二腈、氰基肉桂酸乙酯的Michael加成,室温反应1.5-6h产物收率34-97%。与芳叉丙二腈相比,氰基肉桂酸乙酯反应活性较低。
The investigation of the chemistry of indoles has been, and continues to be, one of the most active areas of heterocyclic chemistry. In particular,3-substituted indole derivatives have received much attention as important building blocks for the synthesis of many natural products and other biologically active compounds. Recently, there are a lot of reports on the synthesis of 3-substituted indoles from indole. In this article, the one-pot synthesis of 3-substituted indole derivatives from indoles, such as bis(indolyl)methane,β-indolylketone,β-indolylalcohol, P-indolylnitro-compound, was reviewed in recent years according to kinds of catalysts used in synthesis of 3-substituted indole derivatives.
Ultrasound has been used more and more frequently in organic synthesis in recent three decades. Compared with traditional methods, a great many of organic reactions can be carried out in higher yields, shorter reaction time or milder conditions under ultrasonic irradiation. In the paper, the principle of sonochemitry and some applications in organic synthesis were reviewed.
The conjugate addition of indoles with 1,5-diaryl-1,4-pentadien-3-ones catalyzed by three catalysts such as aluminum chloride, iodine andβ-toluenesulfonic acid afforded the corresponding products in moderate yields under ultrasound irradiation at room temperature. The acceleration of ultrasound on the reaction, effect of solvent, addition order, frequency of ultrasound and molar ratio of substrate were showed in the results. And a plausible mechanism was proposed.
Synthesis of bis(indolyl)methanes via eletrophilic substitution reactions of indoles with aromatic and ketones catalyzed by silicotungstic acid (SiO2·12WO3·24H2O) was carried out in 50-97% yield within 15-120 min under ultrasound. Compared with traditional methods, this method is more convenient and reactions can be carried out in shorter reaction time and higher yield under ultrasound irradiation. The reaction activities of aromatic aldehydes were higher than aromatic ketones.
Synthesis of 2-((1H-indol-3-yl)(aryl)methyl)malononitrile via the Michael addition of indole with various arylmethylenemalononitriles was carried out in 34-97% yields within 1.5-6 h at r.t using anhydrous zinc chloride as the catalyst under ultrasound irradiation. The reaction activities of ethyl a-cyanocinnamates were lower than arylmethylenemalononitriles.
超声辐射技术在有机合成中的应用研究近二十年来发展非常迅速,与传统的有机合成方法比较,操作方便,反应条件温和,缩短反应时间,提高反应产率。论文介绍超声波的作用原理,综述近几年来超声波在有机合成中的一些应用。
超声辐射下吲哚与1,5-二芳基-1,4-戊二烯-3-酮分别在三氯化铝、碘、对甲苯磺酸等三种不同催化剂催化下的共轭加成反应。考察了超声辐射频率、反应溶剂、底物与催化剂的摩尔比、加料顺序等对反应的影响,推测了可能的反应机理。
以钨硅酸(SiO2·12WO3·24H2O)为催化剂,将吲哚与芳香醛或芳香酮在超声辐射下反应15-120 min,二吲哚甲烷的收率53-97%。与搅拌方法相比,反应时间缩短,反应收率高。与芳香醛相比,芳香酮的反应活性明显降低。
超声辐射能够有效促进无水氯化锌催化的吲哚与芳叉丙二腈、氰基肉桂酸乙酯的Michael加成,室温反应1.5-6h产物收率34-97%。与芳叉丙二腈相比,氰基肉桂酸乙酯反应活性较低。
The investigation of the chemistry of indoles has been, and continues to be, one of the most active areas of heterocyclic chemistry. In particular,3-substituted indole derivatives have received much attention as important building blocks for the synthesis of many natural products and other biologically active compounds. Recently, there are a lot of reports on the synthesis of 3-substituted indoles from indole. In this article, the one-pot synthesis of 3-substituted indole derivatives from indoles, such as bis(indolyl)methane,β-indolylketone,β-indolylalcohol, P-indolylnitro-compound, was reviewed in recent years according to kinds of catalysts used in synthesis of 3-substituted indole derivatives.
Ultrasound has been used more and more frequently in organic synthesis in recent three decades. Compared with traditional methods, a great many of organic reactions can be carried out in higher yields, shorter reaction time or milder conditions under ultrasonic irradiation. In the paper, the principle of sonochemitry and some applications in organic synthesis were reviewed.
The conjugate addition of indoles with 1,5-diaryl-1,4-pentadien-3-ones catalyzed by three catalysts such as aluminum chloride, iodine andβ-toluenesulfonic acid afforded the corresponding products in moderate yields under ultrasound irradiation at room temperature. The acceleration of ultrasound on the reaction, effect of solvent, addition order, frequency of ultrasound and molar ratio of substrate were showed in the results. And a plausible mechanism was proposed.
Synthesis of bis(indolyl)methanes via eletrophilic substitution reactions of indoles with aromatic and ketones catalyzed by silicotungstic acid (SiO2·12WO3·24H2O) was carried out in 50-97% yield within 15-120 min under ultrasound. Compared with traditional methods, this method is more convenient and reactions can be carried out in shorter reaction time and higher yield under ultrasound irradiation. The reaction activities of aromatic aldehydes were higher than aromatic ketones.
Synthesis of 2-((1H-indol-3-yl)(aryl)methyl)malononitrile via the Michael addition of indole with various arylmethylenemalononitriles was carried out in 34-97% yields within 1.5-6 h at r.t using anhydrous zinc chloride as the catalyst under ultrasound irradiation. The reaction activities of ethyl a-cyanocinnamates were lower than arylmethylenemalononitriles.
引文
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