一价铜催化的三类全取代1，2，3-三氮唑的合成方法学研究
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摘要
研究表明，1,4,5-三取代-1,2,3-三氮唑化合物在药物研究开发，新型材料的合成和先导化合物库的建立以及生物缀合等领域发挥着越来越重要的作用。而合成结构多样性的全取代三氮唑就成为进一步研究含三氮唑类药物的构效关系和提高含三氮唑化合物生物活性的重要途径之一。
CuAAC反应是新近提出的一种利用一价铜有效催化有机叠氮化合物和端基炔烃发生1,3-偶极环加成反应生成1,4-二取代-1,2,3-三氮唑化合物的高效新反应。该反应有以下优点：（1）反应条件较温和，对氧气和水不敏感；（2）参与反应的原料和添加剂容易获得；（3）反应所用溶剂能够非常容易去除；（4）反应所得副产物较少，或者产物较易分离；（5）生成产物能够稳定存在。但是利用一价铜催化剂合成1,4,5-三取代-1,2,3-三氮唑（全取代1,2,3-三氮唑）的方法还十分有限，目前大多数合成这类化合物的方法涉及到使用贵金属和膦配体的偶联反应以及C-H键活化反应。这样的方法不仅不具备原子经济性原则，而且往往需要高温等苛刻的反应条件。
因此，利用廉价易得的一价铜催化剂合成具有功能性和结构多样性的1,4,5-三取代-1,2,3-三氮唑化合物是方法学研究领域的一个非常有意义的工作。本论文针对全取代的三氮唑的合成和应用，主要做了以下研究：
第一章综述了近年来三氮唑药物设计的研究进展和合成全取代的1,2,3-三氮唑化合物的方法研究进展。
第二章首次发现了以CuBr/无机碱反应体系，以末端炔和有机叠氮为底物，高效合成5,5’-双（1,2,3-三氮唑）化合物的新方法。该反应体系原料价格低廉，反应条件简便，产率良好，且能够满足底物结构多样性。
第三章通过对CuBr/无机碱反应体系的优化以及反应温度的调节，发展了一种温度调控，在CuBr/无机碱体系中，合成5-炔代-1,4-取代-1,2,3-三氮唑的新方法。并以5-炔代-1,4-取代-1,2,3-三氮唑为中间体，发展了在三氮唑5-位引入羰基、酯基、羧酸、咪唑以及奎喔啉等多样化结构的新方法。
第四章将CuBr/无机碱催化体系扩展到碳环化合物的设计合成中。发展了一种铜催化的通过构建分子内sp2碳碳键合成7元、8元、9元、10元、12元环状分子的简便新方法。
目前，设计合成的全取代1,2,3-三氮唑的生理活性评价以及应用研究还在进行中。
Researches show that1,4,5-trisubstituted-1,2,3-triazoles are playing a more and more important rolein drug research and development, the synthesis of new material and the establishing of lead compoundsbase and biological dimmers. The synthesis of fully-substituted1,2,3-triazoles is becoming an importantway to research the structure activity relationship and improve the biological activity of structure-activitydrugs containing triazoles.
CuAAC (copper-catalyzed azide-alkyne cycloadditions) reaction is proposed recently that using a Cu(I)effective catalytic between organic azides and terminal alkynes to get1,4,5-trisubstituted-1,2,3-triazolesthrough1,3-dipolar cycloaddition reaction. The reaction has the following advantages:(1) it’s a mildreaction, and not sensitive to oxygen or water;(2) the raw material and additive using in reaction are easilyto obtain;(3) the solvent used in the reaction are usually easy to remove;(4) the coproducts may be gettedrarely, that is to say the products could be separated easily;(5) the products are stable.
As the methods of using copper(I) catalyst to synthesis1,4,5-trisubstituted-1,2,3-triazoles(fully-substituted1,2,3-triazoles) are still very scarce now, and most of these compounds synthesismethods need to use precious metals and triarylphosphine ligands through coupling reaction or C-Hactivation reaction——that not only obey the atom economy principle, and also needs high temperature andother harsh reaction conditions usually.
In this case, using CuAAC reaction to get1,4,5-trisubstituted-1,2,3-triazoles with structure diversityeffectively is becoming a more and more meaningful work in the researching of synthetic methodology.
We are interested in the synthesis and the application of fully-substituted1,2,3-trizaoles, and we havedone some research as followed：Firstly, we have reviewed mainly the development of fully-substituted1,2,3-trizaoles in the last few years, and divided the synthesis methods into three categories tointroduce.Secondly we have found the CuBr/inorganic base reaction system first, that is to use organicazides and terminal alkynes as the substrate, and get5,5’-bis (1,2,3-triazole) effectively. The reactionconditions was optimized, and the range of this mothed was expanded. Experimental results show that the price of the raw material in the reaction system is very inexpensive, the reaction conditions are very mildand the yields are good, what's more, the substrate structure diversity is satisfied well.
The next, we have found when the temperature of this system raised in the system of synthesizing5,5’-bis(1,2,3-triazole), the products5-alkynyl-1,2,3-triazoles became the main products instead of5,5’-bis(1,2,3-triazole). And we have made use of1-benzyl-4-phenyl-5-(phenylethynyl)-1H-1,2,3-triazoleas the intermediate, to develop the application of5-alkynyl-1,2,3-triazoles through importing carbonyl,ester, carboxyl, iminazole and quinoxaline ect to get diversified structure of5-substituted-1,2,3-triazoles.
At last, we have expanded the CuBr/inorganic base system to the synthesis of carbon ring compounds,and develop a new convenient method to get seven, eight, nine, ten and twelve-membered ring molecularby building the intramolecular sp2carbon-carbon bond under the function in copper catalysts.
CuAAC反应是新近提出的一种利用一价铜有效催化有机叠氮化合物和端基炔烃发生1,3-偶极环加成反应生成1,4-二取代-1,2,3-三氮唑化合物的高效新反应。该反应有以下优点：（1）反应条件较温和，对氧气和水不敏感；（2）参与反应的原料和添加剂容易获得；（3）反应所用溶剂能够非常容易去除；（4）反应所得副产物较少，或者产物较易分离；（5）生成产物能够稳定存在。但是利用一价铜催化剂合成1,4,5-三取代-1,2,3-三氮唑（全取代1,2,3-三氮唑）的方法还十分有限，目前大多数合成这类化合物的方法涉及到使用贵金属和膦配体的偶联反应以及C-H键活化反应。这样的方法不仅不具备原子经济性原则，而且往往需要高温等苛刻的反应条件。
因此，利用廉价易得的一价铜催化剂合成具有功能性和结构多样性的1,4,5-三取代-1,2,3-三氮唑化合物是方法学研究领域的一个非常有意义的工作。本论文针对全取代的三氮唑的合成和应用，主要做了以下研究：
第一章综述了近年来三氮唑药物设计的研究进展和合成全取代的1,2,3-三氮唑化合物的方法研究进展。
第二章首次发现了以CuBr/无机碱反应体系，以末端炔和有机叠氮为底物，高效合成5,5’-双（1,2,3-三氮唑）化合物的新方法。该反应体系原料价格低廉，反应条件简便，产率良好，且能够满足底物结构多样性。
第三章通过对CuBr/无机碱反应体系的优化以及反应温度的调节，发展了一种温度调控，在CuBr/无机碱体系中，合成5-炔代-1,4-取代-1,2,3-三氮唑的新方法。并以5-炔代-1,4-取代-1,2,3-三氮唑为中间体，发展了在三氮唑5-位引入羰基、酯基、羧酸、咪唑以及奎喔啉等多样化结构的新方法。
第四章将CuBr/无机碱催化体系扩展到碳环化合物的设计合成中。发展了一种铜催化的通过构建分子内sp2碳碳键合成7元、8元、9元、10元、12元环状分子的简便新方法。
目前，设计合成的全取代1,2,3-三氮唑的生理活性评价以及应用研究还在进行中。
Researches show that1,4,5-trisubstituted-1,2,3-triazoles are playing a more and more important rolein drug research and development, the synthesis of new material and the establishing of lead compoundsbase and biological dimmers. The synthesis of fully-substituted1,2,3-triazoles is becoming an importantway to research the structure activity relationship and improve the biological activity of structure-activitydrugs containing triazoles.
CuAAC (copper-catalyzed azide-alkyne cycloadditions) reaction is proposed recently that using a Cu(I)effective catalytic between organic azides and terminal alkynes to get1,4,5-trisubstituted-1,2,3-triazolesthrough1,3-dipolar cycloaddition reaction. The reaction has the following advantages:(1) it’s a mildreaction, and not sensitive to oxygen or water;(2) the raw material and additive using in reaction are easilyto obtain;(3) the solvent used in the reaction are usually easy to remove;(4) the coproducts may be gettedrarely, that is to say the products could be separated easily;(5) the products are stable.
As the methods of using copper(I) catalyst to synthesis1,4,5-trisubstituted-1,2,3-triazoles(fully-substituted1,2,3-triazoles) are still very scarce now, and most of these compounds synthesismethods need to use precious metals and triarylphosphine ligands through coupling reaction or C-Hactivation reaction——that not only obey the atom economy principle, and also needs high temperature andother harsh reaction conditions usually.
In this case, using CuAAC reaction to get1,4,5-trisubstituted-1,2,3-triazoles with structure diversityeffectively is becoming a more and more meaningful work in the researching of synthetic methodology.
We are interested in the synthesis and the application of fully-substituted1,2,3-trizaoles, and we havedone some research as followed：Firstly, we have reviewed mainly the development of fully-substituted1,2,3-trizaoles in the last few years, and divided the synthesis methods into three categories tointroduce.Secondly we have found the CuBr/inorganic base reaction system first, that is to use organicazides and terminal alkynes as the substrate, and get5,5’-bis (1,2,3-triazole) effectively. The reactionconditions was optimized, and the range of this mothed was expanded. Experimental results show that the price of the raw material in the reaction system is very inexpensive, the reaction conditions are very mildand the yields are good, what's more, the substrate structure diversity is satisfied well.
The next, we have found when the temperature of this system raised in the system of synthesizing5,5’-bis(1,2,3-triazole), the products5-alkynyl-1,2,3-triazoles became the main products instead of5,5’-bis(1,2,3-triazole). And we have made use of1-benzyl-4-phenyl-5-(phenylethynyl)-1H-1,2,3-triazoleas the intermediate, to develop the application of5-alkynyl-1,2,3-triazoles through importing carbonyl,ester, carboxyl, iminazole and quinoxaline ect to get diversified structure of5-substituted-1,2,3-triazoles.
At last, we have expanded the CuBr/inorganic base system to the synthesis of carbon ring compounds,and develop a new convenient method to get seven, eight, nine, ten and twelve-membered ring molecularby building the intramolecular sp2carbon-carbon bond under the function in copper catalysts.
引文
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