L-Proline配体效应与三氟乙酰胺基邻位效应共同促进的CuI催化的Ullmann偶联反应在合成杂环化合物中的应用研究
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摘要
铜催化的Ullmann交叉偶联反应在过去的一百多年时间里,获得了巨大的发展,特别是最近十几年,随着配体与催化剂相结合的催化体系的发展,Ullmann反应进入了后Ullmann时代,如何应用Ullmann反应合成具有生理活性的杂环化合物,已成为当今Ullmann反应的研究热点之一。本文主要着眼于Ullmann反应的应用研究,将配体促进效应与邻基促进效应相结合,通过Ullmann反应参与的串联反应,合成具有生理活性的杂环化合物。
在本文的第二章中,我们对氨基酸促进效应和邻基促进效应共同作用下的铜催化的Ullmann偶联反应,应用于合成吡咯并[1,2-a]喹喔啉-4-酮及类似结构杂环化合物的方法进行了研究。我们以2-吡咯甲酸甲酯与邻碘三氟乙酰苯胺的反应为模板,通过考查,得到优化的反应条件。我们以此优化条件,对不同取代的2-吡咯甲酸甲酯和邻卤三氟乙酰苯胺类化合物进行了底物拓展,成功合成了各种取代的吡咯并[1,2-a]喹喔啉-4-酮类杂环化合物。此外,若将邻卤三氟乙酰苯胺类化合物以2-溴-3-三氟乙酰胺基吡啶类化合物替代,则可合成吡啶并[3,2-e]吡咯并[1,2-a]吡嗪-6-酮类杂环化合物;而若以2-吲哚甲酸甲酯替代2-吡咯甲酸甲酯,则可合成吲哚并[1,2-a]喹喔啉-6-酮类杂环化合物。针对实验过程中发现的一些重要现象,我们提出了相应的反应机理进行解释。
在本文的第三章中,我们首先对氨基酸促进效应和邻基促进效应共同作用下的铜催化的Ullmann偶联反应,应用于合成2,3-二氢-1H-咔唑-4-酮类杂环化合物的方法进行研究。我们以邻碘三氟乙酰苯胺与1,3-环己二酮的反应为模板,得到优化的反应条件。我们以此优化条件对各种芳基碘化物进行了底物拓展,均取得了很好的结果。对于反应活性相对较差的芳基溴化物,我们只需将1,3-环己二酮的投料量增加至1.5当量,同时将部分溴化物的偶联反应温度提高至50℃,便能以中等至优秀的收率得到目标产物。接着,我们以1,3-环戊二酮替代1,3-环己二酮,对合成2,3-二氢环戊二烯并[b]吲哚-1-酮类化合物的方法进行了研究。我们以邻碘三氟乙酰苯胺与1,3-环戊二酮的反应为模板,得到优化的反应条件。我们以此优化条件对芳基碘化物、溴化物进行了底物拓展,发现溴化物及部分碘化物需将反应温度提高至50-70℃才能使偶联反应顺利进行。由于采用酸性条件水解脱酰,对于在酸性条件下较稳定的底物,我们以较好的收率得到了最终环化产物,而对酸较敏感的底物,则无法得到产物。此外,针对实验过程中出现的一些现象,我们提出了可能的反应机理加以解释。
Copper-catalyzed Ullmann type cross-coupling reactions have been greatly developed in the last century,especially with the development of the catalysis system which intergrading ligands with catalyst during the last 10 years.How to use Ullmann type reaction to synthesize bioactive heterocycles has become one of the research focuses.In this dissertation,we emphasized on the application of ligand and ortho-substituent promoted/copper catalyzed Ullmann type reactions.We studied some tandem processes in which Ullmann reactions participated of preparing bioactive heterocycles
In the second chapter of this dissertation,we studied the process of preparing pyrrolo[1,2-a]quinoxalin-4(5H)-ones via a copper catalyzed Ullmann type reaction promoted by amino acid ligand and ortho-substituent.We got the optimized reaction conditions using the reaction of methyl 1H-pyrrole-2-carboxylate with 2-iodotrifluoroacetylaniline.Then we tested these conditions by using different 1H-pyrrole-2-carboxylates and 2-halotrifluoroacetylanilines as substates,and obtained the target products successfully.If replacing 2-halotrifluoroacetylanilines by 2-bromo-3-trifluoroacetylamidopyridines,we could get pyrido[3,2-e]pyrrolo[1,2-a] pyrazin-6(5H)-ones.Otherwise,if replacing methyl 1H-pyrrole-2-carboxylate by methyl 1H-indole-2-carboxylate,we could obtain indolo[1,2-a]quinoxalin-6(5H)-ones. We also proposed the reaction mechanism to explain the phenomenon which we observed.
In the third chapter of this dissertation,we firstly studied the process of preparing 2,3-dihydro-1H-carbazol-4(9H)-ones via a copper catalyzed Ullmann type reaction promoted by amino acid ligand and ortho-substituent.We optimized the reaction conditions using the model reaction of 2-iodotrifluoroacetylaniline with cyclohexane-1, 3-dione.Then we tested other aryl iodides under these optimized conditions and got the target products successfully.To bromides,we can obtain the products with middle to excellent yield only need to increase the amount of cyclohexane-1,3-dione to 1.5 equiv and rise the temperature to 50℃for some of the bromides.Secondly we replaced cyclohexane-1,3-dione by cyclopentane-1,3-dione to study the synthesis process of 2,3-dihydrocyelopenta[b]indol-1(4H)-ones.We got the optimized reaction conditions using 2-iodotrifluoroacetylaniline and cyclopentane-1,3-dione as the reaction substrates.Under these optimized conditions,we tested the aryl halides and discovered that the reaction temperature must be at 50-70℃to make the coupling reaction operate successfully for all bromides and some of the iodides.Because of acid hydrolysis,we can only get the products when the substrates were stable in acidic condition.We also proposed the reaction mechanism to explain the phenomenon which we observed.
在本文的第二章中,我们对氨基酸促进效应和邻基促进效应共同作用下的铜催化的Ullmann偶联反应,应用于合成吡咯并[1,2-a]喹喔啉-4-酮及类似结构杂环化合物的方法进行了研究。我们以2-吡咯甲酸甲酯与邻碘三氟乙酰苯胺的反应为模板,通过考查,得到优化的反应条件。我们以此优化条件,对不同取代的2-吡咯甲酸甲酯和邻卤三氟乙酰苯胺类化合物进行了底物拓展,成功合成了各种取代的吡咯并[1,2-a]喹喔啉-4-酮类杂环化合物。此外,若将邻卤三氟乙酰苯胺类化合物以2-溴-3-三氟乙酰胺基吡啶类化合物替代,则可合成吡啶并[3,2-e]吡咯并[1,2-a]吡嗪-6-酮类杂环化合物;而若以2-吲哚甲酸甲酯替代2-吡咯甲酸甲酯,则可合成吲哚并[1,2-a]喹喔啉-6-酮类杂环化合物。针对实验过程中发现的一些重要现象,我们提出了相应的反应机理进行解释。
在本文的第三章中,我们首先对氨基酸促进效应和邻基促进效应共同作用下的铜催化的Ullmann偶联反应,应用于合成2,3-二氢-1H-咔唑-4-酮类杂环化合物的方法进行研究。我们以邻碘三氟乙酰苯胺与1,3-环己二酮的反应为模板,得到优化的反应条件。我们以此优化条件对各种芳基碘化物进行了底物拓展,均取得了很好的结果。对于反应活性相对较差的芳基溴化物,我们只需将1,3-环己二酮的投料量增加至1.5当量,同时将部分溴化物的偶联反应温度提高至50℃,便能以中等至优秀的收率得到目标产物。接着,我们以1,3-环戊二酮替代1,3-环己二酮,对合成2,3-二氢环戊二烯并[b]吲哚-1-酮类化合物的方法进行了研究。我们以邻碘三氟乙酰苯胺与1,3-环戊二酮的反应为模板,得到优化的反应条件。我们以此优化条件对芳基碘化物、溴化物进行了底物拓展,发现溴化物及部分碘化物需将反应温度提高至50-70℃才能使偶联反应顺利进行。由于采用酸性条件水解脱酰,对于在酸性条件下较稳定的底物,我们以较好的收率得到了最终环化产物,而对酸较敏感的底物,则无法得到产物。此外,针对实验过程中出现的一些现象,我们提出了可能的反应机理加以解释。
Copper-catalyzed Ullmann type cross-coupling reactions have been greatly developed in the last century,especially with the development of the catalysis system which intergrading ligands with catalyst during the last 10 years.How to use Ullmann type reaction to synthesize bioactive heterocycles has become one of the research focuses.In this dissertation,we emphasized on the application of ligand and ortho-substituent promoted/copper catalyzed Ullmann type reactions.We studied some tandem processes in which Ullmann reactions participated of preparing bioactive heterocycles
In the second chapter of this dissertation,we studied the process of preparing pyrrolo[1,2-a]quinoxalin-4(5H)-ones via a copper catalyzed Ullmann type reaction promoted by amino acid ligand and ortho-substituent.We got the optimized reaction conditions using the reaction of methyl 1H-pyrrole-2-carboxylate with 2-iodotrifluoroacetylaniline.Then we tested these conditions by using different 1H-pyrrole-2-carboxylates and 2-halotrifluoroacetylanilines as substates,and obtained the target products successfully.If replacing 2-halotrifluoroacetylanilines by 2-bromo-3-trifluoroacetylamidopyridines,we could get pyrido[3,2-e]pyrrolo[1,2-a] pyrazin-6(5H)-ones.Otherwise,if replacing methyl 1H-pyrrole-2-carboxylate by methyl 1H-indole-2-carboxylate,we could obtain indolo[1,2-a]quinoxalin-6(5H)-ones. We also proposed the reaction mechanism to explain the phenomenon which we observed.
In the third chapter of this dissertation,we firstly studied the process of preparing 2,3-dihydro-1H-carbazol-4(9H)-ones via a copper catalyzed Ullmann type reaction promoted by amino acid ligand and ortho-substituent.We optimized the reaction conditions using the model reaction of 2-iodotrifluoroacetylaniline with cyclohexane-1, 3-dione.Then we tested other aryl iodides under these optimized conditions and got the target products successfully.To bromides,we can obtain the products with middle to excellent yield only need to increase the amount of cyclohexane-1,3-dione to 1.5 equiv and rise the temperature to 50℃for some of the bromides.Secondly we replaced cyclohexane-1,3-dione by cyclopentane-1,3-dione to study the synthesis process of 2,3-dihydrocyelopenta[b]indol-1(4H)-ones.We got the optimized reaction conditions using 2-iodotrifluoroacetylaniline and cyclopentane-1,3-dione as the reaction substrates.Under these optimized conditions,we tested the aryl halides and discovered that the reaction temperature must be at 50-70℃to make the coupling reaction operate successfully for all bromides and some of the iodides.Because of acid hydrolysis,we can only get the products when the substrates were stable in acidic condition.We also proposed the reaction mechanism to explain the phenomenon which we observed.
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