亚稳态中间体的研究：基于α-芳基酮醛的原位捕获构建多样化杂环的新方法
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摘要
亚稳态中间体是一类很重要的分子结构体,其拥有反应活性高、易于转化为多样化的新颖结构、以及储存困难等特点,我们设想以原位捕获亚稳态中间体作为反应设计的基点,利用它极容易产生新型的分子骨架和新颖的成键方式的特性,作为开拓新型反应的重要途经和设计策略。通过理性的逻辑设计,将多样化的基元反应有效的集成于一锅中,以串联反应作为媒介,对亚稳态中间体进行原位捕获,构建全面关联的有机分子网络,实现了微观分子的自序化合成,构建了2-酰基苯并噻唑、双吲哚桥联、二芳基甲烷衍生物、咪唑[1,2-a]并吡啶、2-氨基噻唑、α-甲／乙酰氧基芳甲酮、2-烯-1,4-二酮、茚酮骨架、p-咔啉、2-芳酰基喹唑啉等重要结构体。并利用原位捕获亚稳态中间体的策略,完成了天然产物eudistomin Y1-Y6, pityiacitrin以及luotonin F的首次一锅自序化全合成。该策略对一锅合成其他天然产物具有一定的借鉴意义。
下面主要介绍我们在研究原位捕获亚稳态中间体α-芳基酮醛方面的工作：
第一章,首先概述了近年来主要亚稳态中间体的相关进展,然后综述了亚稳态中间体α-芳基酮醛的合成方法及在有机合成中的应用进展,最后,提出了本论文的立题思想。
第二章,近年来,过渡金属催化的C-H键活化及直接官能化得到了飞速地发展,然而,仍然需要进一步发展多样化的方法直接官能化C-H键。我们在研究芳甲基酮与邻氨基苯硫酚的反应中,发现分子碘能促使芳甲基酮sp3C-H键与邻氨基苯硫酚直接偶联生成2-芳酰基苯并噻唑,经过条件优化,发现反应以高达86%的收率得到2-苯甲酰基苯并噻唑。随后,我们仔细地研究了底物的适用范围(不同取代基的芳乙酮、杂芳乙酮、萘乙酮),并成功将芳甲基酮的范围扩展到a,p-不饱和甲基酮。最后,利用在线核磁跟踪和动力学实验有效的观察到反应过程经历的各种中间体。结果表明反应经历了α-碘代芳乙酮和α-芳基酮醛中间体,实现了将碘代、Kornblum氧化、杂环化等多个基元反应自序化集成于一锅中。
第三章,利用多路径偶合串联反应策略,以多样化的底物芳乙烯、芳乙炔、α-羟基芳乙酮和甲原醇(1-芳基乙醇)出发,经历不同的路径生成共同的亚稳态中间体α-芳基酮醛,随后与2-氨基苯硫酚缩合生成2-芳酰基苯并噻唑。通过合理的投料方式,将多个基元反应偶合在一个反应器中。反应对底物芳乙烯、芳乙炔、α-羟基芳乙酮和甲原醇具有很好的广谱性,各种电中性、富电子、缺电子以及杂芳环底物都能很好的适用于该反应。
第四章,吲哚作为一种优势结构受到了人们广泛的关注,双吲哚及多吲哚骨架作为“明星分子”更是人们追捧的对象。我们以芳甲基酮和吲哚及衍生物为原料,实现了分子碘促进的sp3C-H键直接双杂芳基化,合成双吲哚骨架及含杂环的双吲哚骨架。相比传统的金属催化C-H官能化,该方法不需要使用金属、碱和配体即可实现sp3C-H和sp2C-H的偶联。
第五章,在第四章的基础上,进一步发展了碘-三氟甲烷磺酸协同促进的芳甲基酮sp3C-H键双芳基化,以芳甲基酮和N,N-二烷基苯胺等富电子芳环为底物,合成了二-(N,N-二烷基苯胺)-取代甲烷衍生物。通过在线核磁监控及控制实验证明了反应机理,揭示出反应经历了碘代、Kornblum氧化、两次傅克烷基化过程。
第六章,发展了一种可调控的选择性合成2-芳基咪唑[1,2-a]并吡啶和2-芳基-3-(2-吡啶氨基)-咪唑[1,2-a]并吡啶。以相同的底物芳甲基酮和2-氨基吡啶山发,通过控制条件使反应经历不同的亚稳态中间体。当反应在MeOH中进行时,原位生成α-碘代芳乙酮,随后被2-氨基毗啶捕获,合成2-芳基咪唑[1,2-a]并毗啶：当反应在DMSO中进行时,首先原位生成亚稳态中间体α-芳基酮醛,随后两分子2-氨基吡啶捕获α-芳基酮醛,生成2-芳基-3-(2-吡啶氨基)-咪唑[1,2-a]并吡啶。实现了基于相同底物出发,通过路径的调控原位生成不同的亚稳态中间体,选择性合成不同的咪唑[1,2-a]并吡啶骨架。
第七章,在第六章的基础上,我们以芳甲基酮和硫脲出发,在碘和氧化铜的促进下,原位生成亚稳态中间体α-碘代芳乙酮,随后,原位生成的α-碘代芳乙酮被硫脲捕获,生成2-氨基噻唑。接下来,我们进一步研究了底物的适用范围,发现α,β-不饱和甲基酮、1,3-二酮、p-酮酸酯和N-取代硫脲都能很好的适用于该反应。当使用α,β-不饱和甲基酮为底物时,反应能专一性的生成烯键为E-式的产物。
第八章,发展了一种可持续的副产物催化的串联反应策略,实现了串联反应中上游Domino反应的副产物作为催化剂,可持续地催化下游的Domino反应。同时,溶剂作为底物参与了反应,大大提高了整个反应的原子经济性。以芳甲基酮或α,p-不饱和甲基酮为原料,首先,在碘和氧化铜的作用下,原位产生α-碘代芳乙酮,同时,碘和氧化铜转化为副产物碘化亚铜(CuI),随后,碘化亚铜(CuI)又催化了原位生成的α-碘代芳乙酮与溶剂N,N-二甲基甲酰胺(DMF)/N,N-二甲基乙酰胺(DMA)的亲核取代以及水解反应,生成α-甲/乙酰氧基芳甲酮。
第九章,受到多样性导向合成和多路径合成策略的启示,我们发展了一种多样性底物聚焦导向的合成策略。以多样化的底物α-碘代芳乙酮、α-溴代芳乙酮、α-氯代芳乙酮、α-羟基芳乙酮和α-芳基乙醇为原料山发,各自经历不同的反应路径聚焦导向生成共同的中间体α-芳基酮醛,随后,α-芳基酮醛在碘化亚铜的催化下与1,3-二酮或p-酮酸酯发生偶联,合成2-烯-1,4-二酮。通过核磁监测、控制实验以及中间体单晶结构等证实了反应可能经历了Cu(Ⅰ)／Cu(Ⅱ)的催化过程。随后,以Cu(Ⅱ)配合物作为底物详细研究了反应底物的适用范围。最后,通过大量的筛选,发现将多样化的底物α-碘代芳乙酮、α-溴代芳乙酮、α-氯代芳乙酮、α-羟基芳乙酮、α-芳基乙醇和1,3-二酮及催化剂放在一锅中执行,反应能够以很好的收率生成目标产物,进一步证明多样性底物聚焦导向合成是可行的。
第十章,以第九章中合成的2-烯-1,4-二酮为原料,实现了三氯化铝促进的2-烯-1,4-二酮发生Nazarov环化反应,合成了具有两个手性中心的2-酯基-3-芳酰基-1-茚酮,反应儿乎能以定量的收率生成目标产物,且产物的dr值高达99：1。我们详细的研究了原料2-烯-1,4-二酮中底物取代基对反应的影响,发现底物中取代基对反应有很明显的影响。同时,我们通过核磁研究了反应的机理,并观察到2-烯-1,4-二酮与三氯化铝在溶液相中有络合作用,随后,利用核磁研究了溶剂的作用,反应只有在硝基乙烷中才能进行。
第十一章,咔啉是一类重要的杂环骨架,广泛的存在于天然产物和药物分子中,因此,发展简便高效的方法合成咔啉是非常有意义的。本章发展了一种分子碘促进的方法合成α-芳酰基-β-咔啉。以廉价易得的芳甲基酮和色胺及衍生物为原料,直接偶联C-H和N-H键,高收率的合成多样化的α-芳酰基-p-咔啉。当使用色氨酸为底物时,反应能实现C-C键的断裂,同样以高收率生成α-芳酰基-p-咔啉。随后,通过核磁监测和控制实验证实了反应经历α-碘代芳乙酮、α-芳基酮醛和二氢-p-咔啉中间体。最后,我们直接将该方法应用于天然产物eudistomin Y1-Y6和pityiacitrin的一锅合成,可以一锅高收率的合成多样化的目标天然产物。
第十二章,在本论文发展的合成方法和建立的模型的基础上,将其进一步的升华,并应用于天然产物的自序化全合成中。通过理性的逻辑设计,将碘代反应、Kornblum氧化、缩合、加成、氧化芳构化等多步反应自序化的集成在一锅中执行,首次实现了天然产物luotonin F(骆驼宁生物碱)的一锅全合成。反应以廉价易得的2-乙酰基喹啉和2-氨基苯甲酰胺衍生物为原料,在分子碘的促进下,可以高收率的合成天然产物luotonin F及其衍生物。
第十三章,对本篇博士论文的工作进行了总结,并对以后的研究进行了展望。
Metastable-state intermediate is one of the most important molecules, which has the characters of high reactivity, storage difficult and easily transforming to diverserse novel structures. Therefore, we paid our attention on the metastable-state intermediate. Because it was easy to construct novel molecular scaffold. Moreover, it also was an important approach to establish new reaction. Through rational logical design, multifundamental reactions were assembled in one-pot. We have constructed diverse heterocycles by capturing the in situ generated metastable-state intermediates, including2-acyl benzothiazoles, bisindoles,2,2-bis(4-(dimethylamino)phenyl)-1-aryl ethanones, imidazo[1,2-a]pyridines,2-aminothiozoles, a-formyloxy/acetoxy ketones,1,4-enediones,1-indanones, β-carbolines, quinazolin-4(3H)-one. We firstly accomplished the total synthesis of natural products eudistomin Y1-Y6, pityiacitrin, and luotonin F through capturing the metastable-state intermediates approach. This efficient strategy could have significance for directing further research into one-pot synthesis of many natural products.
In this dissertation, we described our works about the metastable-state intermeddiate a-arylglyoxal. At first, we have developed some novel methods for the synthesis of diverse heterocycles by capturing the in situ generated metastable-state intermediate a-arylglyoxal. Furthermore, we have established multipathway coupled domino strategy, focus-oriented domino strategy and sustainable byproduct catalyzed domino strategy. Finally, we have applied the developed methods and strategies to natural products total synthesis. The key discoveries are listed below.
In chapter1, we first summarized the relevant progress about metastable-state intermediates in recent years, and then overviewed of the major synthetic methods to access intermediate a-arylglyoxal and its application in organic synthesis. Subsequently, we proposed the design idea of this dissertation.
In chapter2, transition-metal-catalyzed C-H activation and functionalization has drawn considerable interest in recent years. To further develop diverse methods for direct C-H bond functionalization are still both desirable and valuable. During studying the reaction of aromatic ketones with2-aminothiophenols, we found that molecular iodide could promote sp3C-H of aromatic ketones directly coupling with2-aminothiophenols to afford2-acyl benzothiazoles. After several experimental iterations, the desired product2-benzoyl benzothiazole was furnished in86%yield. Subsequently, the scope of the substrates was investigated in detail, different substituted aromatic ketones, hetero aryl ketones and naphthyl methyl ketones all well suitable in the reaction. We further expanded the scope of the substrates to a,p-unsaturated methyl ketones. We also monitored the reaction process and intermediates via on-line NMR and kinetic experiments. The results disclosed that the reaction underwent a-iodo aryl methyl ketones and a-arylglyoxal intermediates, in which multiple fundamental reactions (iodination, Kornblum oxidation and annulation) were self-sequentially assembled in a single reactor.
In chapter3, based on the multipathway coupled domino strategy, multiform substrates arylethenes, arylacetylenes,2-hydroxy-aromatic ketones, and carbinols were firstly converted into the same intermediates a-arylglyoxals via four distinct pathways. Then, a-arylglyoxals were captured by2-aminothiophenol to afford2-acyl benzothiazoles. Through a logical charging manner, diverse fundamental reactions were integrated in one-pot. The reaction has well tolerant to the multiform substrates (arylethenes, arylacetylenes,2-hydroxy-aromatic ketones, and carbinols), both electron-donating and-withdrawing groups attached to the aryl of substrates were all suitable for this protocol.
In chapter4, indole as privileged scaffold has attracted considerable attention. Moreover, bisindoles as molecular stars were pursued by many synthetic chemists and pharmacologists. We selected aromatic ketones and indole derivatives as starting materials, developed I2-promoted sp3C-H bond dual-(het)arylation protocol for the synthesis of2,2-bisindolyl-l-arylethanones. Compared with the classical metal-catalyzed C-H functionalization, this protocol could directly coupling sp3C-H bond with sp2C-G bond without metal, base, and ligand.
In chapter5, An I2-CF3SO3H synergistic promoted sp3C-H bond diarylation protocol was developed for the synthesis of2,2-bis(4-(dimethylamino)phenyl)-1-aryl ethanones from simple and readily available aryl methyl ketones and N,N-dialkylanilines. We investigated the mechanism and reaction process via on-line NMR and control experiments. The mechanism revealed that the reaction underwent iodination, Kornblum oxidation and hydroarylation three fundamental reactions.
In chapter6, A tunable synthetic protocol was proposed for selective synthesis of2-aryl-imidazo[1,2-a]pyridines and2-aryl-3-(pyridine-2-ylamino)imidazo[1,2-a]pyridines from the same starting materials:aromatic ketones and2-aminopyridines. The reaction performed through different reaction pathways in MeOH and DMSO. When the reaction was carried out in MeOH, aromatic ketones underwent a-halogenation to afford intermediate a-iodo ketones in situ, which were captured by2-aminopyrimidines to obtain2-aryl-imidazo[1,2-a]pyridines. While the reaction performed in DMSO, aromatic ketones were first converted to a-arylglyoxals intermediates. This step was likely followed by condensation with two molecules of2-aminopyrimidines to yield2-aryl-3-(pyridine-2-ylamino)imidazo[1,2-a]pyridines. This protocol could afford different imidazo[1,2-a]pyridines from the same substrates via tunable intermediates in MeOH and DMSO.
In chapter7, we developed a direct protocol for the synthesis of2-aminothiozoles from aromatic ketones and thioureas in the mediate of I2-CuO. First, I2-CuO promoted aromatic ketones to afford a-iodo ketones intermediates, which were captured by thiourea to furnish2-aminothiozoles. Next, we examined the scope of the substrates, and found that α,β-unsaturated methyl ketones, P-keto esters,1,3-diketones and N-methyl thiourea were all suitable for this protocol. When α,β-unsaturated methyl ketones were selected as substrates, the reaction could high selectively obtain the E-conformation products.
In chapter8, we developed a suitable byproduct catalyzed domino strategy, in which the byproducts generated from upstream domino reactions could be utilized to catalyze the downstream domino reactions. Moreover, the solvent also as a substrate took part in the reaction. This strategy can greatly increase the atom-economic of the whole reaction. First,I2-CuO promoted aromatic ketones to afford a-iodo ketones and byproduct CuI. Subsequently, byproduct CuI catalyzed a-iodo ketones reacting with solvent DMF or DMA to afford a-formyloxy and acetoxy ketones. The protocol could highly efficient synthesis of a-formyloxy and acetoxy ketones from aromatic ketones and solvent DMF or DMA.
In chapter9, inspired by the diversity-oriented synthesis and multipathway synthesis strategy, we proposed a multisubstrate focus-oriented synthetic strategy. In the process, different substrates a-halo aromatic ketones,2-hydroxy-aromatic ketones and methyl carbinols were converted into the same intermediate arylglyoxal in situ through different reaction pathways, which was captured by1,3-dicarbonyl compounds to afford1,4-enediones. The on-line NMR monitoring, control experiments and the X-ray structure of intermediate disclosed that the reaction may undergo Cu(I)/Cu(II) catalytic cyclization process. Moreover, we examined the efficiency of Cu(II)-complex with different a-halo aromatic ketones without additional catalyst. After several experimental iterations, we found that diverse substrates a-halo aromatic ketones,2-hydroxy-aromatic ketones and methyl carbinols could self-organized react with1,3-dicarbonyl compounds to afford1,4-enediones through different pathways in one-pot. The result demonstrated that multisubstrate focus-oriented synthetic strategy is feasible under suitable conditions.
In chapter10, we proposed an AlCl3promoted Nazarov cyclization protocol from1,4-enediones to afford1-indanones, in which there were two chiral center. Moreover, the reaction could furnish the product in quantitative yields with high dr (99:1). We observed that the substituent groups of substrates have strong influence on the reaction efficiency. We also investigated the reaction mechanism by NMR spectrum and observed the complexing action between substrate and AlCl3in solution. Furthermore, we studied the influence of solvents and found the reaction only took place in EtNO2.
In chapter11,β-carboline is an important class of heterocycle, which exists widely in natural products and drug molecules. Therefore, the development of a practical and efficient protocol to access β-carboline is both desirable and valuable. We developed a molecular iodide promoted C-H and N-H coupling protocol to access P-carbolines from easy available aromatic ketones and tryptamine derivatives. This method could efficiently obtain diverse β-carbolines. When tryptophan was selected as substrate, the reaction also underwent to furnish P-carbolines in high yields via decarboxylation. We also monitored the reaction process and intermediates via on-line NMR and control experiments. The results disclosed that the reaction underwent a-iodo aryl methyl ketones, a-arylglyoxal and4,9-dihydro-3H-pyrido[3,4-b]indole intermediates. Finally, we directly applied this method to total synthesis of natural product eudistomin Y1-Y6and pityiacitrin. This method could efficiently furnish the desired natural products in one-pot.
In chapter12, based on the previous developed protocols and reaction models, we further applied them to one-pot synthesis of natural products. Through a rational logical design, we assembled multifundamental reactions (iodination, Kornblum oxidation, and annulation) in one-pot and realized the total synthesis of natural product luotonin F in one-pot. The protocol could efficiently synthesize the natural product luotonin F and derivatives from simple and readily available aromatic ketones and2-aminobenzamides.
In chapter13, the summary and outlook of this dissertation was given.
下面主要介绍我们在研究原位捕获亚稳态中间体α-芳基酮醛方面的工作：
第一章,首先概述了近年来主要亚稳态中间体的相关进展,然后综述了亚稳态中间体α-芳基酮醛的合成方法及在有机合成中的应用进展,最后,提出了本论文的立题思想。
第二章,近年来,过渡金属催化的C-H键活化及直接官能化得到了飞速地发展,然而,仍然需要进一步发展多样化的方法直接官能化C-H键。我们在研究芳甲基酮与邻氨基苯硫酚的反应中,发现分子碘能促使芳甲基酮sp3C-H键与邻氨基苯硫酚直接偶联生成2-芳酰基苯并噻唑,经过条件优化,发现反应以高达86%的收率得到2-苯甲酰基苯并噻唑。随后,我们仔细地研究了底物的适用范围(不同取代基的芳乙酮、杂芳乙酮、萘乙酮),并成功将芳甲基酮的范围扩展到a,p-不饱和甲基酮。最后,利用在线核磁跟踪和动力学实验有效的观察到反应过程经历的各种中间体。结果表明反应经历了α-碘代芳乙酮和α-芳基酮醛中间体,实现了将碘代、Kornblum氧化、杂环化等多个基元反应自序化集成于一锅中。
第三章,利用多路径偶合串联反应策略,以多样化的底物芳乙烯、芳乙炔、α-羟基芳乙酮和甲原醇(1-芳基乙醇)出发,经历不同的路径生成共同的亚稳态中间体α-芳基酮醛,随后与2-氨基苯硫酚缩合生成2-芳酰基苯并噻唑。通过合理的投料方式,将多个基元反应偶合在一个反应器中。反应对底物芳乙烯、芳乙炔、α-羟基芳乙酮和甲原醇具有很好的广谱性,各种电中性、富电子、缺电子以及杂芳环底物都能很好的适用于该反应。
第四章,吲哚作为一种优势结构受到了人们广泛的关注,双吲哚及多吲哚骨架作为“明星分子”更是人们追捧的对象。我们以芳甲基酮和吲哚及衍生物为原料,实现了分子碘促进的sp3C-H键直接双杂芳基化,合成双吲哚骨架及含杂环的双吲哚骨架。相比传统的金属催化C-H官能化,该方法不需要使用金属、碱和配体即可实现sp3C-H和sp2C-H的偶联。
第五章,在第四章的基础上,进一步发展了碘-三氟甲烷磺酸协同促进的芳甲基酮sp3C-H键双芳基化,以芳甲基酮和N,N-二烷基苯胺等富电子芳环为底物,合成了二-(N,N-二烷基苯胺)-取代甲烷衍生物。通过在线核磁监控及控制实验证明了反应机理,揭示出反应经历了碘代、Kornblum氧化、两次傅克烷基化过程。
第六章,发展了一种可调控的选择性合成2-芳基咪唑[1,2-a]并吡啶和2-芳基-3-(2-吡啶氨基)-咪唑[1,2-a]并吡啶。以相同的底物芳甲基酮和2-氨基吡啶山发,通过控制条件使反应经历不同的亚稳态中间体。当反应在MeOH中进行时,原位生成α-碘代芳乙酮,随后被2-氨基毗啶捕获,合成2-芳基咪唑[1,2-a]并毗啶：当反应在DMSO中进行时,首先原位生成亚稳态中间体α-芳基酮醛,随后两分子2-氨基吡啶捕获α-芳基酮醛,生成2-芳基-3-(2-吡啶氨基)-咪唑[1,2-a]并吡啶。实现了基于相同底物出发,通过路径的调控原位生成不同的亚稳态中间体,选择性合成不同的咪唑[1,2-a]并吡啶骨架。
第七章,在第六章的基础上,我们以芳甲基酮和硫脲出发,在碘和氧化铜的促进下,原位生成亚稳态中间体α-碘代芳乙酮,随后,原位生成的α-碘代芳乙酮被硫脲捕获,生成2-氨基噻唑。接下来,我们进一步研究了底物的适用范围,发现α,β-不饱和甲基酮、1,3-二酮、p-酮酸酯和N-取代硫脲都能很好的适用于该反应。当使用α,β-不饱和甲基酮为底物时,反应能专一性的生成烯键为E-式的产物。
第八章,发展了一种可持续的副产物催化的串联反应策略,实现了串联反应中上游Domino反应的副产物作为催化剂,可持续地催化下游的Domino反应。同时,溶剂作为底物参与了反应,大大提高了整个反应的原子经济性。以芳甲基酮或α,p-不饱和甲基酮为原料,首先,在碘和氧化铜的作用下,原位产生α-碘代芳乙酮,同时,碘和氧化铜转化为副产物碘化亚铜(CuI),随后,碘化亚铜(CuI)又催化了原位生成的α-碘代芳乙酮与溶剂N,N-二甲基甲酰胺(DMF)/N,N-二甲基乙酰胺(DMA)的亲核取代以及水解反应,生成α-甲/乙酰氧基芳甲酮。
第九章,受到多样性导向合成和多路径合成策略的启示,我们发展了一种多样性底物聚焦导向的合成策略。以多样化的底物α-碘代芳乙酮、α-溴代芳乙酮、α-氯代芳乙酮、α-羟基芳乙酮和α-芳基乙醇为原料山发,各自经历不同的反应路径聚焦导向生成共同的中间体α-芳基酮醛,随后,α-芳基酮醛在碘化亚铜的催化下与1,3-二酮或p-酮酸酯发生偶联,合成2-烯-1,4-二酮。通过核磁监测、控制实验以及中间体单晶结构等证实了反应可能经历了Cu(Ⅰ)／Cu(Ⅱ)的催化过程。随后,以Cu(Ⅱ)配合物作为底物详细研究了反应底物的适用范围。最后,通过大量的筛选,发现将多样化的底物α-碘代芳乙酮、α-溴代芳乙酮、α-氯代芳乙酮、α-羟基芳乙酮、α-芳基乙醇和1,3-二酮及催化剂放在一锅中执行,反应能够以很好的收率生成目标产物,进一步证明多样性底物聚焦导向合成是可行的。
第十章,以第九章中合成的2-烯-1,4-二酮为原料,实现了三氯化铝促进的2-烯-1,4-二酮发生Nazarov环化反应,合成了具有两个手性中心的2-酯基-3-芳酰基-1-茚酮,反应儿乎能以定量的收率生成目标产物,且产物的dr值高达99：1。我们详细的研究了原料2-烯-1,4-二酮中底物取代基对反应的影响,发现底物中取代基对反应有很明显的影响。同时,我们通过核磁研究了反应的机理,并观察到2-烯-1,4-二酮与三氯化铝在溶液相中有络合作用,随后,利用核磁研究了溶剂的作用,反应只有在硝基乙烷中才能进行。
第十一章,咔啉是一类重要的杂环骨架,广泛的存在于天然产物和药物分子中,因此,发展简便高效的方法合成咔啉是非常有意义的。本章发展了一种分子碘促进的方法合成α-芳酰基-β-咔啉。以廉价易得的芳甲基酮和色胺及衍生物为原料,直接偶联C-H和N-H键,高收率的合成多样化的α-芳酰基-p-咔啉。当使用色氨酸为底物时,反应能实现C-C键的断裂,同样以高收率生成α-芳酰基-p-咔啉。随后,通过核磁监测和控制实验证实了反应经历α-碘代芳乙酮、α-芳基酮醛和二氢-p-咔啉中间体。最后,我们直接将该方法应用于天然产物eudistomin Y1-Y6和pityiacitrin的一锅合成,可以一锅高收率的合成多样化的目标天然产物。
第十二章,在本论文发展的合成方法和建立的模型的基础上,将其进一步的升华,并应用于天然产物的自序化全合成中。通过理性的逻辑设计,将碘代反应、Kornblum氧化、缩合、加成、氧化芳构化等多步反应自序化的集成在一锅中执行,首次实现了天然产物luotonin F(骆驼宁生物碱)的一锅全合成。反应以廉价易得的2-乙酰基喹啉和2-氨基苯甲酰胺衍生物为原料,在分子碘的促进下,可以高收率的合成天然产物luotonin F及其衍生物。
第十三章,对本篇博士论文的工作进行了总结,并对以后的研究进行了展望。
Metastable-state intermediate is one of the most important molecules, which has the characters of high reactivity, storage difficult and easily transforming to diverserse novel structures. Therefore, we paid our attention on the metastable-state intermediate. Because it was easy to construct novel molecular scaffold. Moreover, it also was an important approach to establish new reaction. Through rational logical design, multifundamental reactions were assembled in one-pot. We have constructed diverse heterocycles by capturing the in situ generated metastable-state intermediates, including2-acyl benzothiazoles, bisindoles,2,2-bis(4-(dimethylamino)phenyl)-1-aryl ethanones, imidazo[1,2-a]pyridines,2-aminothiozoles, a-formyloxy/acetoxy ketones,1,4-enediones,1-indanones, β-carbolines, quinazolin-4(3H)-one. We firstly accomplished the total synthesis of natural products eudistomin Y1-Y6, pityiacitrin, and luotonin F through capturing the metastable-state intermediates approach. This efficient strategy could have significance for directing further research into one-pot synthesis of many natural products.
In this dissertation, we described our works about the metastable-state intermeddiate a-arylglyoxal. At first, we have developed some novel methods for the synthesis of diverse heterocycles by capturing the in situ generated metastable-state intermediate a-arylglyoxal. Furthermore, we have established multipathway coupled domino strategy, focus-oriented domino strategy and sustainable byproduct catalyzed domino strategy. Finally, we have applied the developed methods and strategies to natural products total synthesis. The key discoveries are listed below.
In chapter1, we first summarized the relevant progress about metastable-state intermediates in recent years, and then overviewed of the major synthetic methods to access intermediate a-arylglyoxal and its application in organic synthesis. Subsequently, we proposed the design idea of this dissertation.
In chapter2, transition-metal-catalyzed C-H activation and functionalization has drawn considerable interest in recent years. To further develop diverse methods for direct C-H bond functionalization are still both desirable and valuable. During studying the reaction of aromatic ketones with2-aminothiophenols, we found that molecular iodide could promote sp3C-H of aromatic ketones directly coupling with2-aminothiophenols to afford2-acyl benzothiazoles. After several experimental iterations, the desired product2-benzoyl benzothiazole was furnished in86%yield. Subsequently, the scope of the substrates was investigated in detail, different substituted aromatic ketones, hetero aryl ketones and naphthyl methyl ketones all well suitable in the reaction. We further expanded the scope of the substrates to a,p-unsaturated methyl ketones. We also monitored the reaction process and intermediates via on-line NMR and kinetic experiments. The results disclosed that the reaction underwent a-iodo aryl methyl ketones and a-arylglyoxal intermediates, in which multiple fundamental reactions (iodination, Kornblum oxidation and annulation) were self-sequentially assembled in a single reactor.
In chapter3, based on the multipathway coupled domino strategy, multiform substrates arylethenes, arylacetylenes,2-hydroxy-aromatic ketones, and carbinols were firstly converted into the same intermediates a-arylglyoxals via four distinct pathways. Then, a-arylglyoxals were captured by2-aminothiophenol to afford2-acyl benzothiazoles. Through a logical charging manner, diverse fundamental reactions were integrated in one-pot. The reaction has well tolerant to the multiform substrates (arylethenes, arylacetylenes,2-hydroxy-aromatic ketones, and carbinols), both electron-donating and-withdrawing groups attached to the aryl of substrates were all suitable for this protocol.
In chapter4, indole as privileged scaffold has attracted considerable attention. Moreover, bisindoles as molecular stars were pursued by many synthetic chemists and pharmacologists. We selected aromatic ketones and indole derivatives as starting materials, developed I2-promoted sp3C-H bond dual-(het)arylation protocol for the synthesis of2,2-bisindolyl-l-arylethanones. Compared with the classical metal-catalyzed C-H functionalization, this protocol could directly coupling sp3C-H bond with sp2C-G bond without metal, base, and ligand.
In chapter5, An I2-CF3SO3H synergistic promoted sp3C-H bond diarylation protocol was developed for the synthesis of2,2-bis(4-(dimethylamino)phenyl)-1-aryl ethanones from simple and readily available aryl methyl ketones and N,N-dialkylanilines. We investigated the mechanism and reaction process via on-line NMR and control experiments. The mechanism revealed that the reaction underwent iodination, Kornblum oxidation and hydroarylation three fundamental reactions.
In chapter6, A tunable synthetic protocol was proposed for selective synthesis of2-aryl-imidazo[1,2-a]pyridines and2-aryl-3-(pyridine-2-ylamino)imidazo[1,2-a]pyridines from the same starting materials:aromatic ketones and2-aminopyridines. The reaction performed through different reaction pathways in MeOH and DMSO. When the reaction was carried out in MeOH, aromatic ketones underwent a-halogenation to afford intermediate a-iodo ketones in situ, which were captured by2-aminopyrimidines to obtain2-aryl-imidazo[1,2-a]pyridines. While the reaction performed in DMSO, aromatic ketones were first converted to a-arylglyoxals intermediates. This step was likely followed by condensation with two molecules of2-aminopyrimidines to yield2-aryl-3-(pyridine-2-ylamino)imidazo[1,2-a]pyridines. This protocol could afford different imidazo[1,2-a]pyridines from the same substrates via tunable intermediates in MeOH and DMSO.
In chapter7, we developed a direct protocol for the synthesis of2-aminothiozoles from aromatic ketones and thioureas in the mediate of I2-CuO. First, I2-CuO promoted aromatic ketones to afford a-iodo ketones intermediates, which were captured by thiourea to furnish2-aminothiozoles. Next, we examined the scope of the substrates, and found that α,β-unsaturated methyl ketones, P-keto esters,1,3-diketones and N-methyl thiourea were all suitable for this protocol. When α,β-unsaturated methyl ketones were selected as substrates, the reaction could high selectively obtain the E-conformation products.
In chapter8, we developed a suitable byproduct catalyzed domino strategy, in which the byproducts generated from upstream domino reactions could be utilized to catalyze the downstream domino reactions. Moreover, the solvent also as a substrate took part in the reaction. This strategy can greatly increase the atom-economic of the whole reaction. First,I2-CuO promoted aromatic ketones to afford a-iodo ketones and byproduct CuI. Subsequently, byproduct CuI catalyzed a-iodo ketones reacting with solvent DMF or DMA to afford a-formyloxy and acetoxy ketones. The protocol could highly efficient synthesis of a-formyloxy and acetoxy ketones from aromatic ketones and solvent DMF or DMA.
In chapter9, inspired by the diversity-oriented synthesis and multipathway synthesis strategy, we proposed a multisubstrate focus-oriented synthetic strategy. In the process, different substrates a-halo aromatic ketones,2-hydroxy-aromatic ketones and methyl carbinols were converted into the same intermediate arylglyoxal in situ through different reaction pathways, which was captured by1,3-dicarbonyl compounds to afford1,4-enediones. The on-line NMR monitoring, control experiments and the X-ray structure of intermediate disclosed that the reaction may undergo Cu(I)/Cu(II) catalytic cyclization process. Moreover, we examined the efficiency of Cu(II)-complex with different a-halo aromatic ketones without additional catalyst. After several experimental iterations, we found that diverse substrates a-halo aromatic ketones,2-hydroxy-aromatic ketones and methyl carbinols could self-organized react with1,3-dicarbonyl compounds to afford1,4-enediones through different pathways in one-pot. The result demonstrated that multisubstrate focus-oriented synthetic strategy is feasible under suitable conditions.
In chapter10, we proposed an AlCl3promoted Nazarov cyclization protocol from1,4-enediones to afford1-indanones, in which there were two chiral center. Moreover, the reaction could furnish the product in quantitative yields with high dr (99:1). We observed that the substituent groups of substrates have strong influence on the reaction efficiency. We also investigated the reaction mechanism by NMR spectrum and observed the complexing action between substrate and AlCl3in solution. Furthermore, we studied the influence of solvents and found the reaction only took place in EtNO2.
In chapter11,β-carboline is an important class of heterocycle, which exists widely in natural products and drug molecules. Therefore, the development of a practical and efficient protocol to access β-carboline is both desirable and valuable. We developed a molecular iodide promoted C-H and N-H coupling protocol to access P-carbolines from easy available aromatic ketones and tryptamine derivatives. This method could efficiently obtain diverse β-carbolines. When tryptophan was selected as substrate, the reaction also underwent to furnish P-carbolines in high yields via decarboxylation. We also monitored the reaction process and intermediates via on-line NMR and control experiments. The results disclosed that the reaction underwent a-iodo aryl methyl ketones, a-arylglyoxal and4,9-dihydro-3H-pyrido[3,4-b]indole intermediates. Finally, we directly applied this method to total synthesis of natural product eudistomin Y1-Y6and pityiacitrin. This method could efficiently furnish the desired natural products in one-pot.
In chapter12, based on the previous developed protocols and reaction models, we further applied them to one-pot synthesis of natural products. Through a rational logical design, we assembled multifundamental reactions (iodination, Kornblum oxidation, and annulation) in one-pot and realized the total synthesis of natural product luotonin F in one-pot. The protocol could efficiently synthesize the natural product luotonin F and derivatives from simple and readily available aromatic ketones and2-aminobenzamides.
In chapter13, the summary and outlook of this dissertation was given.
引文
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