金催化氧化炔烃合成α-羰基及四、五元氮氧杂环化合物的研究
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摘要
作为有机化学研究最受关注的领域之一，均相金催化化学在近几年得到了蓬勃的发展，也取得了大量颇具价值的研究成果。金具有特殊的π-酸性，可以与烯炔类π-键配位起到活化π-键的作用，进而发生多种类型的反应，例如与亲核试剂反应、氧化偶联反应以及炔丙酯重排反应等。
许多均相金催化反应都涉及金卡宾中间体的概念。金卡宾作为金属卡宾的一种，不仅可以通过金属配合物催化重氮卡宾分解生成，而且在许多亲核进攻反应中，表现出类似重氮卡宾的反应性质。-羰基金卡宾作为一种独特的卡宾结构，通常是由金配位的炔烃与含有亲核性氧的氧化剂反应得到的。在许多已经报道的均相金催化氧化反应中，-羰基金卡宾中间体表现出了较高的活性，能够进行多种官能团转化反应。
本论文主要研究金催化分子间氧化末端炔基生成的-羰基金卡宾中间体在羰基化合物和四、五元含氮氧杂环化合物合成中的应用，研究工作包括以下五个部分：
1.本文发展了一种金催化分子间氧化炔烃合成-乙酰氧基酮类化合物的通用方法。-乙酰氧基酮是一种在有机药物合成领域有着重要作用的中间体化合物，本文以末端炔烃为初始原料，利用金催化氧化反应以较好的产率一步合成该化合物。反应机理包括金催化分子间氧化炔基生成-羰基金卡宾中间体，然后金卡宾中间体与乙酸反应实现O-H键插入或者与乙酸乙酯反应实现C-O键插入。该方法利用-羰基金卡宾中间体代替已报道方法中危险的-重氮羰基化合物，而且反应过程不要求无水无氧条件，操作及后处理简便。
2．本文探索了一种金催化分子间氧化炔烃合成羰基甲磺酸酯类化合物的方法。反应机理包括金催化分子间氧化炔基生成-羰基金卡宾及THF分子C-O键断裂开环反应。本文以末端炔烃为初始原料，利用金催化氧化反应以较好的产率一步合成该化合物。此外，将反应溶剂换成四氢吡喃、1,4-二氧六环等其他的含氧杂环时，反应依然可以顺利进行，并且以良好的产率获得相应的杂环开环产物。
3．本文建立了一种通过金催化氧化末端炔烃生成-羰基金卡宾中间体与N,N-二甲基甲酰胺反应生成1,3-二酮类化合物的新方法，实现了-羰基金卡宾中间体的C-N键插入反应。本文以末端炔烃为初始原料，利用金催化氧化反应以较好的产率一步合成该化合物。该反应的反应条件极其温和，官能团兼容性强。
4．本文探索了一种金催化分子间氧化炔基磺酰胺化合物高效合成3-氮杂环酮类化合物的方法。反应机理包括金催化分子间氧化炔基生成-羰基金卡宾及卡宾分子内N-H键插入环化。对甲苯磺酰基作为反应中氨基的保护基，保证了反应的顺利进行。3-氮杂环酮作为药物研发中一类重要的生物活性结构，其合成方法受到有机化学家们的深入研究。本方法以首先通过一锅法制备炔基磺酰胺底物，然后利用金催化氧化反应以较好的产率一步合成该化合物。
5．本文利用了已知的金催化氧化末端炔烃与腈反应生成2,5-二取代噁唑的方法，合成了一系列5-芳基-2-甲基噁唑化合物，并对新合成的化合物进行了体外抗癌活性测试。抗癌活性测试结果表明，新合成的噁唑化合物，均具有一定的体外癌细胞抑制活性，其中5位萘基取代的化合物活性最优，与对照药顺铂的活性基本持平。
As one of the most hot topics in organic chemistry, homogeneous gold catalysishas been in-depth researched in recent years, and a lot of valuable results have beenachieved. Gold complexes are rather unique soft Lewis and π acids, which can be uesdas catalyst for the activation of C-C multibonds toward various types of reactions,such as nucleophilic reactions, oxidative coupling reactions, and propargyl esterrearrangement reactions.
Many gold-mediated homogeneous catalytic reactions take place via goldcarbene intermediates. As one of metal carbene complexes, gold carbene could beobtained through the metal complex catalyzed decomposition of diazo carbene. And inmany nucleophilic reactions, gold carbenes are similar with diazo carbenes. Gold
-oxo carbenoid intermediates can be generated from inter-and intramolecularoxidation of alkynes by nucleophilic oxygen-atom donor groups. In a large of reportedgold-mediated addition-elimination reactions,-oxo gold carbenoids can undergonucleophilic attack by a variety of groups, leading to cascade reactions and theconstruction of new skeletons.
This thesis is concerned with studies on the synthesis of carbonyl compounds andfour-or five-membered nitrogen-and oxygen-containing heterocycles by gold-catalyzed intermolecular oxidation of terminal alkynes generated-carbonyl carbeneintermediates. It is divided into five parts as follows:
（1）A general solution for the synthesis of various-acetoxy ketone has beendeveloped. This reaction uses readily available terminal alkynes as substrates andproceeds without the exclusion of moisture or air. Notably,-acetoxy ketones, ashighly valuable substrates for drug research, can be prepared in one step from alkynesin fairly good yields. Mechanistically, reactive a-oxo gold carbenes is generated asintermediates through intermolecular oxidation of alkynes and subsequentintermolecular O-H insertion with acetic acid or C-O insertion with ehtyl acetate. Thissafe and efficient generation of gold carbenes offers a potentially general entry into
-oxo metal carbene chemistry without using hazardous diazo ketones.
（2）Carbonyl mesylate esters are efficiently synthesized in moderate to highyields from gold-catalyzed reaction of alkynes. Mechanistically, a-oxo gold carbenesare generated as intermediates through intermolecular oxidation of alkynes andsubsequent THF ring-opening reaction. Notably, the products can be prepared in onestep from terminal alkynes as the starting material. Further more, the reaction solventwas replaced with tetrahydropyran,1,4-dioxane, or other oxygen-containingheterocyclic rings, the reactions could be carried out smoothly and obtained thecorresponding products in good yields.
（3） The efficient intermolecular reaction of gold carbene intermediatesgenerated via gold-catalyzed alkyne oxidation has been realized usingN,N-dimethylformamide as both the reagent and the reaction solvent, offering agenerally efficient synthesis of1,3-diketones to achieve the C-N bond insertionreaction of-carbonyl carbene intermediates. The reaction conditions areexceptionally mild, and a range of functional groups are easily tolerated.
（4）A practical and flexible synthesis of azetidin-3-ones and pyrrolidin-3-onehas been developed. The key reaction is a gold-catalyzed oxidative cyclization ofN-propargylsulfonamides. Mechanistically, a-oxo gold carbenes are generated asintermediates through intermolecular alkyne oxidation and subsequent intramolecularN-H insertion. The use of p-toluenesulfonyl as the protecting group does not influencethe reaction. Owing to the versatility of azetidin-3-ones and pyrrolidin-3-ones asimportant biologically active structures in drug research, extensive studies on theirpreparation have been well documented. Homopropargylic N-sulfonylamines aresynthesized via an efficient and simple one-pot procedure, then one step synthesis ofazetidin-3-ones and pyrrolidin-3-ones using gold catalytic oxidation ofhomopropargylic N-sulfonylamines.
（5） A series of5-aryl-2-methyloxazole derivatives are synthesized viagold-catalyzed alkyne oxidation. All of the compounds have been screened for theirantiproliferative activities against MCF-7cell （human breast carcinoma）, A549cell（human lung carcinoma）and Hela cell（Human cervical carcinoma）lines in vitro.The results reveal that oxazole compounds exhibit the inhibitory activities against thecancer cell lines, and naphthalen-2-yl at C-5position of oxazole ring are the best.
许多均相金催化反应都涉及金卡宾中间体的概念。金卡宾作为金属卡宾的一种，不仅可以通过金属配合物催化重氮卡宾分解生成，而且在许多亲核进攻反应中，表现出类似重氮卡宾的反应性质。-羰基金卡宾作为一种独特的卡宾结构，通常是由金配位的炔烃与含有亲核性氧的氧化剂反应得到的。在许多已经报道的均相金催化氧化反应中，-羰基金卡宾中间体表现出了较高的活性，能够进行多种官能团转化反应。
本论文主要研究金催化分子间氧化末端炔基生成的-羰基金卡宾中间体在羰基化合物和四、五元含氮氧杂环化合物合成中的应用，研究工作包括以下五个部分：
1.本文发展了一种金催化分子间氧化炔烃合成-乙酰氧基酮类化合物的通用方法。-乙酰氧基酮是一种在有机药物合成领域有着重要作用的中间体化合物，本文以末端炔烃为初始原料，利用金催化氧化反应以较好的产率一步合成该化合物。反应机理包括金催化分子间氧化炔基生成-羰基金卡宾中间体，然后金卡宾中间体与乙酸反应实现O-H键插入或者与乙酸乙酯反应实现C-O键插入。该方法利用-羰基金卡宾中间体代替已报道方法中危险的-重氮羰基化合物，而且反应过程不要求无水无氧条件，操作及后处理简便。
2．本文探索了一种金催化分子间氧化炔烃合成羰基甲磺酸酯类化合物的方法。反应机理包括金催化分子间氧化炔基生成-羰基金卡宾及THF分子C-O键断裂开环反应。本文以末端炔烃为初始原料，利用金催化氧化反应以较好的产率一步合成该化合物。此外，将反应溶剂换成四氢吡喃、1,4-二氧六环等其他的含氧杂环时，反应依然可以顺利进行，并且以良好的产率获得相应的杂环开环产物。
3．本文建立了一种通过金催化氧化末端炔烃生成-羰基金卡宾中间体与N,N-二甲基甲酰胺反应生成1,3-二酮类化合物的新方法，实现了-羰基金卡宾中间体的C-N键插入反应。本文以末端炔烃为初始原料，利用金催化氧化反应以较好的产率一步合成该化合物。该反应的反应条件极其温和，官能团兼容性强。
4．本文探索了一种金催化分子间氧化炔基磺酰胺化合物高效合成3-氮杂环酮类化合物的方法。反应机理包括金催化分子间氧化炔基生成-羰基金卡宾及卡宾分子内N-H键插入环化。对甲苯磺酰基作为反应中氨基的保护基，保证了反应的顺利进行。3-氮杂环酮作为药物研发中一类重要的生物活性结构，其合成方法受到有机化学家们的深入研究。本方法以首先通过一锅法制备炔基磺酰胺底物，然后利用金催化氧化反应以较好的产率一步合成该化合物。
5．本文利用了已知的金催化氧化末端炔烃与腈反应生成2,5-二取代噁唑的方法，合成了一系列5-芳基-2-甲基噁唑化合物，并对新合成的化合物进行了体外抗癌活性测试。抗癌活性测试结果表明，新合成的噁唑化合物，均具有一定的体外癌细胞抑制活性，其中5位萘基取代的化合物活性最优，与对照药顺铂的活性基本持平。
As one of the most hot topics in organic chemistry, homogeneous gold catalysishas been in-depth researched in recent years, and a lot of valuable results have beenachieved. Gold complexes are rather unique soft Lewis and π acids, which can be uesdas catalyst for the activation of C-C multibonds toward various types of reactions,such as nucleophilic reactions, oxidative coupling reactions, and propargyl esterrearrangement reactions.
Many gold-mediated homogeneous catalytic reactions take place via goldcarbene intermediates. As one of metal carbene complexes, gold carbene could beobtained through the metal complex catalyzed decomposition of diazo carbene. And inmany nucleophilic reactions, gold carbenes are similar with diazo carbenes. Gold
-oxo carbenoid intermediates can be generated from inter-and intramolecularoxidation of alkynes by nucleophilic oxygen-atom donor groups. In a large of reportedgold-mediated addition-elimination reactions,-oxo gold carbenoids can undergonucleophilic attack by a variety of groups, leading to cascade reactions and theconstruction of new skeletons.
This thesis is concerned with studies on the synthesis of carbonyl compounds andfour-or five-membered nitrogen-and oxygen-containing heterocycles by gold-catalyzed intermolecular oxidation of terminal alkynes generated-carbonyl carbeneintermediates. It is divided into five parts as follows:
（1）A general solution for the synthesis of various-acetoxy ketone has beendeveloped. This reaction uses readily available terminal alkynes as substrates andproceeds without the exclusion of moisture or air. Notably,-acetoxy ketones, ashighly valuable substrates for drug research, can be prepared in one step from alkynesin fairly good yields. Mechanistically, reactive a-oxo gold carbenes is generated asintermediates through intermolecular oxidation of alkynes and subsequentintermolecular O-H insertion with acetic acid or C-O insertion with ehtyl acetate. Thissafe and efficient generation of gold carbenes offers a potentially general entry into
-oxo metal carbene chemistry without using hazardous diazo ketones.
（2）Carbonyl mesylate esters are efficiently synthesized in moderate to highyields from gold-catalyzed reaction of alkynes. Mechanistically, a-oxo gold carbenesare generated as intermediates through intermolecular oxidation of alkynes andsubsequent THF ring-opening reaction. Notably, the products can be prepared in onestep from terminal alkynes as the starting material. Further more, the reaction solventwas replaced with tetrahydropyran,1,4-dioxane, or other oxygen-containingheterocyclic rings, the reactions could be carried out smoothly and obtained thecorresponding products in good yields.
（3） The efficient intermolecular reaction of gold carbene intermediatesgenerated via gold-catalyzed alkyne oxidation has been realized usingN,N-dimethylformamide as both the reagent and the reaction solvent, offering agenerally efficient synthesis of1,3-diketones to achieve the C-N bond insertionreaction of-carbonyl carbene intermediates. The reaction conditions areexceptionally mild, and a range of functional groups are easily tolerated.
（4）A practical and flexible synthesis of azetidin-3-ones and pyrrolidin-3-onehas been developed. The key reaction is a gold-catalyzed oxidative cyclization ofN-propargylsulfonamides. Mechanistically, a-oxo gold carbenes are generated asintermediates through intermolecular alkyne oxidation and subsequent intramolecularN-H insertion. The use of p-toluenesulfonyl as the protecting group does not influencethe reaction. Owing to the versatility of azetidin-3-ones and pyrrolidin-3-ones asimportant biologically active structures in drug research, extensive studies on theirpreparation have been well documented. Homopropargylic N-sulfonylamines aresynthesized via an efficient and simple one-pot procedure, then one step synthesis ofazetidin-3-ones and pyrrolidin-3-ones using gold catalytic oxidation ofhomopropargylic N-sulfonylamines.
（5） A series of5-aryl-2-methyloxazole derivatives are synthesized viagold-catalyzed alkyne oxidation. All of the compounds have been screened for theirantiproliferative activities against MCF-7cell （human breast carcinoma）, A549cell（human lung carcinoma）and Hela cell（Human cervical carcinoma）lines in vitro.The results reveal that oxazole compounds exhibit the inhibitory activities against thecancer cell lines, and naphthalen-2-yl at C-5position of oxazole ring are the best.
引文
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