机械力促进的N-去甲酰化，交叉脱氢偶联反应用于制备喹啉/四氢异喹啉类衍生物
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摘要
随着医药化工行业的迅猛发展,大量的有机溶剂被耗费,同时在其生产、纯化和循环利用过程中存在危害性、环境污染和能源消耗等问题,导致我们对溶剂的依赖越来越不可持续。无溶剂反应避免了由于使用溶剂所带来的危险性、毒害性以及成本增加等缺点,成为近年来研究热点之一。机械球磨,作为促进无溶剂反应的一种新型反应方式,具备多种优势,已逐渐成为有机合成反应的一种有效手段。
本论文的主要工作包括机械球磨条件下的去甲酰化反应和交叉脱氢偶联反应。具体内容如下：
(1)简要介绍了机械化学的发展概况,综述了机械球磨技术在有机合成中的应用及影响反应的各类因素。
(2)在高速球磨条件下,利用固体碱,实现对N-甲酰基-1,2-二氢喹啉类化合物的去甲酰基-芳构化反应。以固体NaOH为碱,聚乙二醇(PEG)2000为添加剂,NaCl为助磨剂进行无溶剂去甲酰基-芳构化反应,为2-芳(杂芳)基喹啉衍生物的合成提供了一条方便、快速、环境友好的路线。与传统方法相比,反应中不需要任何有毒有害的有机溶剂,时间短,收率高,底物适用范围广,后处理方便,充分体现了“绿色化学”的理念。此外,反应中所使用的添加剂及助磨剂能够多次循环使用并保持较高的反应活性。
(3)在高速球磨条件下,二氯二氰基苯醌(DDO)促进四氢异喹啉(sp3C-H)与三种不同杂化类型的底物(spC-H,aryl-sp2C-H, sp3C-H)进行交叉脱氢偶联反应(CDC)。本文首次将机械球磨技术用于交叉脱氢偶联反应中,利用安全稳定且易于存储的DDQ作为氧化剂进行反应。对于硝基烷烃类化合物及丙二腈来说,在非金属催化下即可得到R--C-H的官能团化产物。对于炔烃和吲哚类化合物来说,反应中使用铜质研磨球,既作为研磨介质又作为反应催化剂,同样能够高效地制备得到氧化偶联产物；其中催化剂能够简单的从反应混合物中取出并重复使用。该类反应既具有CDC反应高原子经济性的特点,又具备机械球磨反应高效、快速、无溶剂的优势,为制备具有潜在抗肿瘤活性的四氢异喹啉衍生物提供了一条合理的途径。
(4)在高速球磨条件下,利用2,6-吡啶二恶唑啉(Pybox)为手性配体,实现四氢异喹啉(sp3C-H)与炔烃(spC-H)的不对称交叉脱氢偶联(CDC)反应。高速球磨反应作为促进无溶剂反应的有效方式,被越来越多的运用于各类无溶剂有机反应中,但球磨条件下的对映选择性反应少有报道。本文首次采用这种非传统的反应方式进行以四氢异喹啉为底物的不对称交叉脱氢偶联反应,从而制备得到一系列具有潜在生物活性的手性四氢异喹啉衍生物,拓宽了机械球磨技术在不对称有机合成中的应用范围。这类反应具有时间短,操作简单,后处理方便,催化剂易于回收等优势。
(5)机械力促进的交叉脱氢偶联反应用于吡喹酮药物中间体的制备及其衍生反应的研究。将机械球磨条件下的交叉脱氢偶联反应运用到吡喹酮关键中间体的制备中,使反应更为快速,高效。以N-对甲氧基苯基四氢异喹啉为底物,经脱氢偶联,催化氢化及氧化去保护三步反应制备得到1-氨基甲基-1,2,3,4-四氢异喹啉中间体,为构建吡喹酮及其类似物中间体提供一种新颖、有效的方法。此外,在对毗喹酮合成路线进行优化设计过程中,发现一种新型机械研磨条件下的无溶剂N-酰基四氢异喹啉氧化开环反应。文中对该类反应的底物范围、反应条件、选择性及反应机理等进行了较全面地研究,同时还将该反应在传统方式下进行以作比较。
With the rapid development of the pharmaceutical and chemical industry, current dependence on solvents appears increasingly unsustainable since it is wasteful of fossil-derived materials, environmentally problematic, hazardous and energy-demanding with regard to solvent production, purification and recycling. Solvent-free reactions avoid the dangers, toxic and costs-increase posed by the use of solvents, become one of the hot-spot recently. As a new way to promote solvent-free reactions, mechanical milling has various advantages and becomes an effective tool for organic synthesis reactions.
In this thesis, investigations are focused on the deformylation and cross dehydrogenation coupling reaction under mechanical milling condition. The main contents include the following five aspects.
(1) Briefly describes the development of the mechanical chemistry, the overview of mechanical milling in organic synthesis as well as various influencing factors.
(2) Under high speed ball milling conditions, using solid base to realize the deformylation and aromatization reaction of N-formyl-1,2-dihydroquinolines. With solid NaOH as base, PEG2000as additive, NaCl as grinding aid, this solvent-free reaction providing a fast, convenient and environmentally friendly route for the preparation of2-aryl(heteroaryl)-quinolines. Compared with traditional deformylation methods, the reaction did not require any toxic organic solvents, Also, short reaction time, high yields, wide generality and simple isolation of the production all make this method fully embodied the concept of green chemistry. Additionally, additives and grinding aids used in the reaction could be reused many times with a high reaction activity.
(3) Under high speed ball milling conditions, using DDQ to promote the cross-dehydrogenative coupling reaction (CDC) between tetrahydroisoquinoline (sp3C-H) with three different type of hybrid substrates (sp C-H, aryl-sp2C-H, sp3C-H). Mechanical milling technique has been first applied to the cross-dehydrogenative coupling reaction. DDQ, a safe, stable and easy-store oxidant was used in these reactions. For nitroalkanes and malononitrile, R-C-H-functionalized products were obtained without any metal catalyst. For alkynes and indoles, copper balls were used both as the reacting catalyst and milling balls; the recovery of the catalyst would be as simple as removing the copper ball from the reaction media. Such reactions have both the characteristic of high atom economy of CDC reaction, and the advantages of fast, efficient and solvent-free of mechanical milling reaction. This method provides a reasonable approach for the preparation of tetrahydroisoquinoline derivatives having potential anti-tumor activity.
(4) Under high speed ball milling conditions, asymmetric alkynylation of prochiral sp3C-H bonds for the preparation of optically active tetrahydroisoquinolines was achieved by using PyBox as chiral ligand. Although High Speed Ball-Milling (HSBM) technique has been increasingly used in synthetic organic chemistry to promote several solvent-free reactions, only a few enantioselective reactions have been explored under HSBM conditions. The present work is attractive in the search of the application of this nonconventional methodology for the preparation of optically active tetrahydroisoquinoline derivatives through asymmetric CDC reactions. This could represent an interesting challenge for the development of enantioselective reactions in a ball mill. Fast, simple operation and easy to reuse the catalyst are advantages of the reaction.
(5) Mechanically activated cross-dehydrogenative coupling reaction was applied for the preparation of praziquantel intermediates, while a derivative reaction was studied. Mechanically promoted CDC reaction was firstly applied to prepare the key intermediates of praziquantel, the reaction is more rapid and efficient. N-(4-methoxyphenyl) tetrahydroisoquinoline was used as the substrate, through cross-dehydrogenative coupling, catalytic hydrogenation, and oxidative deprotection three-step reactions to give1-aminomethyl-1,2,3,4-tetrahydroisoquinoline intermediates, which providing a novel and effective method for constructing praziquantel and its analogues intermediates. In addition, during the design and optimization process in praziquantel synthetic routes, a new type of solvent-free oxidative ring-opening reaction of N-acyl-tetrahydroisoquinoline under ball mill condition was discovered. In this reaction, a relative comprehensive study was carried out on the range of substrate, reaction conditions, selectivity and mechanism. For comparison, the reaction was also carried out in the traditional condition.
本论文的主要工作包括机械球磨条件下的去甲酰化反应和交叉脱氢偶联反应。具体内容如下：
(1)简要介绍了机械化学的发展概况,综述了机械球磨技术在有机合成中的应用及影响反应的各类因素。
(2)在高速球磨条件下,利用固体碱,实现对N-甲酰基-1,2-二氢喹啉类化合物的去甲酰基-芳构化反应。以固体NaOH为碱,聚乙二醇(PEG)2000为添加剂,NaCl为助磨剂进行无溶剂去甲酰基-芳构化反应,为2-芳(杂芳)基喹啉衍生物的合成提供了一条方便、快速、环境友好的路线。与传统方法相比,反应中不需要任何有毒有害的有机溶剂,时间短,收率高,底物适用范围广,后处理方便,充分体现了“绿色化学”的理念。此外,反应中所使用的添加剂及助磨剂能够多次循环使用并保持较高的反应活性。
(3)在高速球磨条件下,二氯二氰基苯醌(DDO)促进四氢异喹啉(sp3C-H)与三种不同杂化类型的底物(spC-H,aryl-sp2C-H, sp3C-H)进行交叉脱氢偶联反应(CDC)。本文首次将机械球磨技术用于交叉脱氢偶联反应中,利用安全稳定且易于存储的DDQ作为氧化剂进行反应。对于硝基烷烃类化合物及丙二腈来说,在非金属催化下即可得到R--C-H的官能团化产物。对于炔烃和吲哚类化合物来说,反应中使用铜质研磨球,既作为研磨介质又作为反应催化剂,同样能够高效地制备得到氧化偶联产物；其中催化剂能够简单的从反应混合物中取出并重复使用。该类反应既具有CDC反应高原子经济性的特点,又具备机械球磨反应高效、快速、无溶剂的优势,为制备具有潜在抗肿瘤活性的四氢异喹啉衍生物提供了一条合理的途径。
(4)在高速球磨条件下,利用2,6-吡啶二恶唑啉(Pybox)为手性配体,实现四氢异喹啉(sp3C-H)与炔烃(spC-H)的不对称交叉脱氢偶联(CDC)反应。高速球磨反应作为促进无溶剂反应的有效方式,被越来越多的运用于各类无溶剂有机反应中,但球磨条件下的对映选择性反应少有报道。本文首次采用这种非传统的反应方式进行以四氢异喹啉为底物的不对称交叉脱氢偶联反应,从而制备得到一系列具有潜在生物活性的手性四氢异喹啉衍生物,拓宽了机械球磨技术在不对称有机合成中的应用范围。这类反应具有时间短,操作简单,后处理方便,催化剂易于回收等优势。
(5)机械力促进的交叉脱氢偶联反应用于吡喹酮药物中间体的制备及其衍生反应的研究。将机械球磨条件下的交叉脱氢偶联反应运用到吡喹酮关键中间体的制备中,使反应更为快速,高效。以N-对甲氧基苯基四氢异喹啉为底物,经脱氢偶联,催化氢化及氧化去保护三步反应制备得到1-氨基甲基-1,2,3,4-四氢异喹啉中间体,为构建吡喹酮及其类似物中间体提供一种新颖、有效的方法。此外,在对毗喹酮合成路线进行优化设计过程中,发现一种新型机械研磨条件下的无溶剂N-酰基四氢异喹啉氧化开环反应。文中对该类反应的底物范围、反应条件、选择性及反应机理等进行了较全面地研究,同时还将该反应在传统方式下进行以作比较。
With the rapid development of the pharmaceutical and chemical industry, current dependence on solvents appears increasingly unsustainable since it is wasteful of fossil-derived materials, environmentally problematic, hazardous and energy-demanding with regard to solvent production, purification and recycling. Solvent-free reactions avoid the dangers, toxic and costs-increase posed by the use of solvents, become one of the hot-spot recently. As a new way to promote solvent-free reactions, mechanical milling has various advantages and becomes an effective tool for organic synthesis reactions.
In this thesis, investigations are focused on the deformylation and cross dehydrogenation coupling reaction under mechanical milling condition. The main contents include the following five aspects.
(1) Briefly describes the development of the mechanical chemistry, the overview of mechanical milling in organic synthesis as well as various influencing factors.
(2) Under high speed ball milling conditions, using solid base to realize the deformylation and aromatization reaction of N-formyl-1,2-dihydroquinolines. With solid NaOH as base, PEG2000as additive, NaCl as grinding aid, this solvent-free reaction providing a fast, convenient and environmentally friendly route for the preparation of2-aryl(heteroaryl)-quinolines. Compared with traditional deformylation methods, the reaction did not require any toxic organic solvents, Also, short reaction time, high yields, wide generality and simple isolation of the production all make this method fully embodied the concept of green chemistry. Additionally, additives and grinding aids used in the reaction could be reused many times with a high reaction activity.
(3) Under high speed ball milling conditions, using DDQ to promote the cross-dehydrogenative coupling reaction (CDC) between tetrahydroisoquinoline (sp3C-H) with three different type of hybrid substrates (sp C-H, aryl-sp2C-H, sp3C-H). Mechanical milling technique has been first applied to the cross-dehydrogenative coupling reaction. DDQ, a safe, stable and easy-store oxidant was used in these reactions. For nitroalkanes and malononitrile, R-C-H-functionalized products were obtained without any metal catalyst. For alkynes and indoles, copper balls were used both as the reacting catalyst and milling balls; the recovery of the catalyst would be as simple as removing the copper ball from the reaction media. Such reactions have both the characteristic of high atom economy of CDC reaction, and the advantages of fast, efficient and solvent-free of mechanical milling reaction. This method provides a reasonable approach for the preparation of tetrahydroisoquinoline derivatives having potential anti-tumor activity.
(4) Under high speed ball milling conditions, asymmetric alkynylation of prochiral sp3C-H bonds for the preparation of optically active tetrahydroisoquinolines was achieved by using PyBox as chiral ligand. Although High Speed Ball-Milling (HSBM) technique has been increasingly used in synthetic organic chemistry to promote several solvent-free reactions, only a few enantioselective reactions have been explored under HSBM conditions. The present work is attractive in the search of the application of this nonconventional methodology for the preparation of optically active tetrahydroisoquinoline derivatives through asymmetric CDC reactions. This could represent an interesting challenge for the development of enantioselective reactions in a ball mill. Fast, simple operation and easy to reuse the catalyst are advantages of the reaction.
(5) Mechanically activated cross-dehydrogenative coupling reaction was applied for the preparation of praziquantel intermediates, while a derivative reaction was studied. Mechanically promoted CDC reaction was firstly applied to prepare the key intermediates of praziquantel, the reaction is more rapid and efficient. N-(4-methoxyphenyl) tetrahydroisoquinoline was used as the substrate, through cross-dehydrogenative coupling, catalytic hydrogenation, and oxidative deprotection three-step reactions to give1-aminomethyl-1,2,3,4-tetrahydroisoquinoline intermediates, which providing a novel and effective method for constructing praziquantel and its analogues intermediates. In addition, during the design and optimization process in praziquantel synthetic routes, a new type of solvent-free oxidative ring-opening reaction of N-acyl-tetrahydroisoquinoline under ball mill condition was discovered. In this reaction, a relative comprehensive study was carried out on the range of substrate, reaction conditions, selectivity and mechanism. For comparison, the reaction was also carried out in the traditional condition.
引文
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