氧化吲哚衍生物的合成研究
发布时间：2018-08-10 20:30
【摘要】：本论文包括两个部分：1.以N-芳基丙烯酰胺为底物与重氮盐在光催化作用下进行反应合成一系列氧化吲哚化合物；2.以N-芳基丙烯酰胺为底物与TMSCF3在醋酸碘苯氧化作用下合成含三氟甲基的氧化吲哚。 1.N-芳基丙烯酰胺与重氮盐反应合成了27种相应的氧化吲哚衍生物，反应过程中，我们探讨了反应条件对反应的影响，在光催化剂的选择上对比Ru(bpy)3Cl2·6H2O、Ru(bpy)3(PF6)2、曙红Y结果发现催化剂Ru(bpy)3Cl2·6H2O使得产物产率达到最高，在反应溶剂的选择上以MeOH效果最好，，投料比1a:2a以1:2.5反应产率达到最高。然后利用核磁共振氢谱、质谱和单晶衍射等现代分析测试手段对这些化合物进行结构表征。 2.N-芳基丙烯酰胺与TMSCF3反应合成了19种相应的氧化吲哚衍生物，反应过程中对条件优化发现以NMP为溶剂，PhI(OAc)2作为氧化剂，NaOAc作为碱时反应以较高收率得到含三氟甲基的氧化吲哚衍生物。然后利用核磁共振氢谱、质谱和单晶衍射等现代分析测试手段对这些化合物进行结构表征。
[Abstract]:This thesis includes two parts: 1. A series of oxidized indoles were synthesized by photocatalytic reaction of N-aryl acrylamide with diazo salt. N aryl acrylamide was used as substrate to synthesize indoles containing trifluoromethyl in the presence of iodobenzene acetate in the presence of TMSCF3. 1. N aryl acrylamide reacted with diazo salt to synthesize 27 corresponding indoles. The effect of reaction conditions on the reaction was discussed. Compared with Ru (bpy) 3Cl2 6H 2O Ru (bpy) 3 (PF6) 2, the eosin Y catalyst Ru (bpy) 3Cl2 6H2O made the yield of the product reach the highest, and MeOH was the best in the selection of reaction solvent. The feed ratio 1a:2a reached the highest yield at 1: 2.5 reaction. The structures of these compounds were characterized by nuclear magnetic resonance spectroscopy, mass spectrometry and single crystal diffraction. 2. N- aryl acrylamide reacted with TMSCF3 to synthesize 19 corresponding oxyindole derivatives. When NMP was used as oxidant and NaOAc as base, trifluoromethyl oxyindole derivatives were obtained in high yield. The structures of these compounds were characterized by nuclear magnetic resonance spectroscopy, mass spectrometry and single crystal diffraction.
【学位授予单位】：郑州大学
【学位级别】：硕士
【学位授予年份】：2014
【分类号】：R914
本文编号：2176115
[Abstract]:This thesis includes two parts: 1. A series of oxidized indoles were synthesized by photocatalytic reaction of N-aryl acrylamide with diazo salt. N aryl acrylamide was used as substrate to synthesize indoles containing trifluoromethyl in the presence of iodobenzene acetate in the presence of TMSCF3. 1. N aryl acrylamide reacted with diazo salt to synthesize 27 corresponding indoles. The effect of reaction conditions on the reaction was discussed. Compared with Ru (bpy) 3Cl2 6H 2O Ru (bpy) 3 (PF6) 2, the eosin Y catalyst Ru (bpy) 3Cl2 6H2O made the yield of the product reach the highest, and MeOH was the best in the selection of reaction solvent. The feed ratio 1a:2a reached the highest yield at 1: 2.5 reaction. The structures of these compounds were characterized by nuclear magnetic resonance spectroscopy, mass spectrometry and single crystal diffraction. 2. N- aryl acrylamide reacted with TMSCF3 to synthesize 19 corresponding oxyindole derivatives. When NMP was used as oxidant and NaOAc as base, trifluoromethyl oxyindole derivatives were obtained in high yield. The structures of these compounds were characterized by nuclear magnetic resonance spectroscopy, mass spectrometry and single crystal diffraction.
【学位授予单位】：郑州大学
【学位级别】：硕士
【学位授予年份】：2014
【分类号】：R914
【共引文献】
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2 黄璇;刘雄伟;郭丰敏;景德红;周英;刘雄利;余章彪;;通过自由基历程合成3-季碳氧化吲哚的研究进展[J];铜仁学院学报;2014年04期
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2 王贺;基于α-羰基二硫缩烯酮多米诺成环反应研究[D];东北师范大学;2014年
3 杨志勇;一些含氮杂环化合物及其衍生物的合成[D];湖南大学;2014年
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1 叶超;基于串联反应构建几类含氮杂环化合物[D];江西师范大学;2013年
2 张磊;铼催化的烯烃与高价碘的脱羧烷基化—芳基化反应研究[D];河北师范大学;2014年
本文编号：2176115
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