二茂铁基苯基甲烷衍生物及含氮杂环衍生物的合成研究
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摘要
本论文主要分为两个部分,第一是二茂铁基苯基甲醇与亲核试剂(吲哚、芳胺)的反应研究,第二是N-杂环衍生物的合成研究。
在第一部分工作中,利用超声波技术,研究了二茂铁基苯基甲醇与吲哚的反应,合成了一系列含二茂铁基苯基甲烷的吲哚衍生物。该反应条件温和,操作简便,反应时间较短,产率中等偏上。在此基础上,我们还研究了二茂铁基苯基甲醇的芳胺化反应,在硝酸铈铵(CAN)的催化作用下,二茂铁基苯基甲醇与芳香胺能较快地发生反应,生成N-烷基化产物。该法的反应条件温和并且产率也较高。
在第二部分工作中,以邻溴苯甲醛或邻氯苯甲醛与3-(芳基氨基)-5,5-二甲基-2-环己烯酮类化合物为底物,通过Buchwald-Hartwig偶联,进而进行分子内的环化反应,合成了一系列喹啉衍生物。从中我们发现,当使用邻氯苯甲醛时反应产率较低,而使用邻溴苯甲醛时产率适中或较好。
我们以2-氰基吡啶、芳香醛和乙酸铵为底物,通过三组分一锅法,合成了一系列2,4,5-三芳基取代的咪唑化合物。该方法简单可行,但是也有其不足之处即底物范围有限且产率普遍较低。当前,我们正努力提高该反应的产率并对其机理作进一步的研究。
The thesis is mainly composed of two parts. The first part focus on the reaction of (ferrocenyl)(phenyl)methanol with nucleophiles such as indoles and arylamine. The second part is based on the synthesis of N-heterocycle derivatives.
In the first section, the neucleophilic substitution reaction of (ferrocenyl)(phenyl)methanol with indoles were investigated, a variety of indole derivatives could be easily synthesized under the ultrasonic condition. The reaction is mild, manipulated easy and even afford high yields in short time. In addition, we focus on the reaction of amination of (ferrocenyl)(phenyl)methanol. In the presence of Ceric nitrate ammonium (CAN), (ferrocenyl)(phenyl)methanol react with arylamines quickly, affording the product of N-alkylation. Condition of the reaction is tender and the yield is good.
In the second section, we synthesized a series of quinoline derivatives with 3-(arylamino)-5,5-dimethylcyclohex-2-enone and 2-chloro or 2-bromobenzaldehyde via Buchwald-Hartwig coupling followed by the intramolecular cyclization. The substituent group of halogen at the o-position of formyl in the substrate has great affect on the reantion.
we synthesized a series of 2,4,5-trisubstituted imidazole derivatives through three-component one-pot reaction from substrates of cyanopyridine, aldehyde and ammonium acetate. The method is simple and feasible, however, it has some defects such as substrates limitation and low yields. Presently we are attempting to improve the yield and working on the mechanism of the reaction.
在第一部分工作中,利用超声波技术,研究了二茂铁基苯基甲醇与吲哚的反应,合成了一系列含二茂铁基苯基甲烷的吲哚衍生物。该反应条件温和,操作简便,反应时间较短,产率中等偏上。在此基础上,我们还研究了二茂铁基苯基甲醇的芳胺化反应,在硝酸铈铵(CAN)的催化作用下,二茂铁基苯基甲醇与芳香胺能较快地发生反应,生成N-烷基化产物。该法的反应条件温和并且产率也较高。
在第二部分工作中,以邻溴苯甲醛或邻氯苯甲醛与3-(芳基氨基)-5,5-二甲基-2-环己烯酮类化合物为底物,通过Buchwald-Hartwig偶联,进而进行分子内的环化反应,合成了一系列喹啉衍生物。从中我们发现,当使用邻氯苯甲醛时反应产率较低,而使用邻溴苯甲醛时产率适中或较好。
我们以2-氰基吡啶、芳香醛和乙酸铵为底物,通过三组分一锅法,合成了一系列2,4,5-三芳基取代的咪唑化合物。该方法简单可行,但是也有其不足之处即底物范围有限且产率普遍较低。当前,我们正努力提高该反应的产率并对其机理作进一步的研究。
The thesis is mainly composed of two parts. The first part focus on the reaction of (ferrocenyl)(phenyl)methanol with nucleophiles such as indoles and arylamine. The second part is based on the synthesis of N-heterocycle derivatives.
In the first section, the neucleophilic substitution reaction of (ferrocenyl)(phenyl)methanol with indoles were investigated, a variety of indole derivatives could be easily synthesized under the ultrasonic condition. The reaction is mild, manipulated easy and even afford high yields in short time. In addition, we focus on the reaction of amination of (ferrocenyl)(phenyl)methanol. In the presence of Ceric nitrate ammonium (CAN), (ferrocenyl)(phenyl)methanol react with arylamines quickly, affording the product of N-alkylation. Condition of the reaction is tender and the yield is good.
In the second section, we synthesized a series of quinoline derivatives with 3-(arylamino)-5,5-dimethylcyclohex-2-enone and 2-chloro or 2-bromobenzaldehyde via Buchwald-Hartwig coupling followed by the intramolecular cyclization. The substituent group of halogen at the o-position of formyl in the substrate has great affect on the reantion.
we synthesized a series of 2,4,5-trisubstituted imidazole derivatives through three-component one-pot reaction from substrates of cyanopyridine, aldehyde and ammonium acetate. The method is simple and feasible, however, it has some defects such as substrates limitation and low yields. Presently we are attempting to improve the yield and working on the mechanism of the reaction.
引文
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