N-杂环卡宾催化应用于有机小分子合成的研究
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摘要
卡宾在有机反应中是一类较活泼、易参与反应的化合物。和一般类型的卡宾结构特点相类似,N-杂环卡宾(NHC)也是一种电中性的化合物,卡宾碳原子是二价的,其最外层具有六个电子。自从1991年Arduengo等人报道的第一个稳定的亲核性N-杂环卡宾—咪唑-2-碳烯以来,NHC在有机合成中的应用也越来越广泛,除了其作为金属催化反应中的优良配体外,N-杂环卡宾作为有机小分子催化剂在有机合成中也已经取得了丰硕的研究成果。本论文我们将NHC催化的有机反应应用到了有机小分子的合成中,对非常有用的有机分子如苯偶酰、吡咯、噻吩并吲哚、螺环丁内酯吲哚酮等化合物的合成进行了研究,取得了一些有意义的实验结果:
1.苯并咪唑盐作为卡宾催化前体盐,在水中催化安息香缩合,并应用一锅煮的实验方法,中间产物不经处理直接与加入的氧化剂三氯化铁反应,非常方便快捷的得到苯偶酰化合物。
2.研究了噻唑盐催化的多组分反应合成多取代吡咯化合物的方法。首先通过噻唑盐催化醛与苯并咪唑查尔酮反应得到一系列1, 4-二羰基化合物,并在此基础上应用一锅煮Paal?Knorr反应合成得到了一系列文献未有报道的苯并咪唑基多取代吡咯衍生物。化合物都通过红外、核磁等表征手段对其进行了表征,同时应用X-Ray单晶衍射法测定了其中一个化合物的晶体结构。
3.以取代苯胺为原料合成得到一系列靛红化合物,经还原、缩合得3-芳亚甲基-2-吲哚酮,然后用噻唑盐催化合成得到重要中间体1, 4-二羰基吲哚酮衍生物,最后用Lawson试剂硫代缩合得到噻吩并吲哚化合物并通过了红外、核磁的表征。
4.对NHC催化合成螺环丁内酯吲哚酮衍生物的反应作了深入研究,拓展了反应底物,同时发现了底物对产物构型的影响规律,合成得到并表征了一系列新的螺环丁内酯吲哚酮衍生物,并用X-Ray单晶衍射法确定了一个产物的绝对构型。
5.发现了N-杂环卡宾催化的芳香醛亚胺分子内偶联反应并对其做了初步研究;设计合成了分子内Stetter关环反应分子,但关环未获成功而是得到了酯化产物。
Carbene, a most investigated reactive species in the field of organic chemistry, is a typical structural features, N-heterocyclic carbenes (NHC) are neutral and possess a bivalent carbon atom with an electron sextet. Since the first reports of stable nucleophilic carbenes—imidazol-2-ylidene by Arduengo et al. in 1991, the broad application of NHC in organic synthesis has been impressively demonstrated. Beside their role as excellent ligands in metal-based catalytic reactions, organocatalytic carbene catalysis has emerged as an exceptionally fruitful research area in synthetic organic chemistry. In this thesis, with the application of NHC catalysis, we have synthesized some useful oganic small moleculars such as benzil, pyrroles, thieno[2, 3-b]indole, spiro butyrolactone oxindole and so on. The main interesting results are as fellows:
1. A simple and convenient one-pot procedure is reported for the synthesis of 1,2-diketones from corresponding benzoin-type condensation reaction of aromatic aldehydes in water with benzimidazolium salt as condensation catalyst and ferric chloride as oxidizing reagent.
2. A multicomponent synthesis of highly substituted pyrroles catalyzed by thiazolium salts has been disclosed. Fistly, a series of 1, 4-dicarbonyl compounds were obtained from aldehyde and benzimidazole-chalcone with thiazolium salts as catalyst. The subsequent addition of various amines promotes a Paal?Knorr reaction, affording the desired pyrrole nucleus in an efficient one-pot process. The intermediate 1, 4-dicarbonyl compounds and highly substituted pyrroles were all characterized by NMR, IR spectra and one single crystal structure of them was determined by X-ray diffraction method.
3. The substituted aniline was selected as the starting material, using Sandmeyer methodology to form isatin compounds. Then 3-arylideneindolin-2-one was obtained via Wolff-Kishner-Huang Reaction and condensation reaction. The most impotant intermediate 1, 4-dicarbonyl oxindole compounds were synthesized catalyted by thiazolium salts. At last, a series of thieno[2, 3-b]indoles were obtained promoted by the Lawson’reagent. The targent compounds were all fully characterized by NMR,IR spectra.
4. We had done deep research to synthesis of spiro butyrolactone oxindole with NHC as catalyst, resulting that the corresponding product’s configuration is determined by the structure of the starting substrat. We also obtained and had characterized a series of new spiro butyrolactone oxindole and had determined a product’s absolute configuration by X-Ray crystal diffraction.
5. We had discovered the intramolecular coupling reaction of aldehyde imines catalyzed by NHC and had got some preliminary result; We got the esterification products instead of the desired compounds of intramolecular Stetter cyclization.
1.苯并咪唑盐作为卡宾催化前体盐,在水中催化安息香缩合,并应用一锅煮的实验方法,中间产物不经处理直接与加入的氧化剂三氯化铁反应,非常方便快捷的得到苯偶酰化合物。
2.研究了噻唑盐催化的多组分反应合成多取代吡咯化合物的方法。首先通过噻唑盐催化醛与苯并咪唑查尔酮反应得到一系列1, 4-二羰基化合物,并在此基础上应用一锅煮Paal?Knorr反应合成得到了一系列文献未有报道的苯并咪唑基多取代吡咯衍生物。化合物都通过红外、核磁等表征手段对其进行了表征,同时应用X-Ray单晶衍射法测定了其中一个化合物的晶体结构。
3.以取代苯胺为原料合成得到一系列靛红化合物,经还原、缩合得3-芳亚甲基-2-吲哚酮,然后用噻唑盐催化合成得到重要中间体1, 4-二羰基吲哚酮衍生物,最后用Lawson试剂硫代缩合得到噻吩并吲哚化合物并通过了红外、核磁的表征。
4.对NHC催化合成螺环丁内酯吲哚酮衍生物的反应作了深入研究,拓展了反应底物,同时发现了底物对产物构型的影响规律,合成得到并表征了一系列新的螺环丁内酯吲哚酮衍生物,并用X-Ray单晶衍射法确定了一个产物的绝对构型。
5.发现了N-杂环卡宾催化的芳香醛亚胺分子内偶联反应并对其做了初步研究;设计合成了分子内Stetter关环反应分子,但关环未获成功而是得到了酯化产物。
Carbene, a most investigated reactive species in the field of organic chemistry, is a typical structural features, N-heterocyclic carbenes (NHC) are neutral and possess a bivalent carbon atom with an electron sextet. Since the first reports of stable nucleophilic carbenes—imidazol-2-ylidene by Arduengo et al. in 1991, the broad application of NHC in organic synthesis has been impressively demonstrated. Beside their role as excellent ligands in metal-based catalytic reactions, organocatalytic carbene catalysis has emerged as an exceptionally fruitful research area in synthetic organic chemistry. In this thesis, with the application of NHC catalysis, we have synthesized some useful oganic small moleculars such as benzil, pyrroles, thieno[2, 3-b]indole, spiro butyrolactone oxindole and so on. The main interesting results are as fellows:
1. A simple and convenient one-pot procedure is reported for the synthesis of 1,2-diketones from corresponding benzoin-type condensation reaction of aromatic aldehydes in water with benzimidazolium salt as condensation catalyst and ferric chloride as oxidizing reagent.
2. A multicomponent synthesis of highly substituted pyrroles catalyzed by thiazolium salts has been disclosed. Fistly, a series of 1, 4-dicarbonyl compounds were obtained from aldehyde and benzimidazole-chalcone with thiazolium salts as catalyst. The subsequent addition of various amines promotes a Paal?Knorr reaction, affording the desired pyrrole nucleus in an efficient one-pot process. The intermediate 1, 4-dicarbonyl compounds and highly substituted pyrroles were all characterized by NMR, IR spectra and one single crystal structure of them was determined by X-ray diffraction method.
3. The substituted aniline was selected as the starting material, using Sandmeyer methodology to form isatin compounds. Then 3-arylideneindolin-2-one was obtained via Wolff-Kishner-Huang Reaction and condensation reaction. The most impotant intermediate 1, 4-dicarbonyl oxindole compounds were synthesized catalyted by thiazolium salts. At last, a series of thieno[2, 3-b]indoles were obtained promoted by the Lawson’reagent. The targent compounds were all fully characterized by NMR,IR spectra.
4. We had done deep research to synthesis of spiro butyrolactone oxindole with NHC as catalyst, resulting that the corresponding product’s configuration is determined by the structure of the starting substrat. We also obtained and had characterized a series of new spiro butyrolactone oxindole and had determined a product’s absolute configuration by X-Ray crystal diffraction.
5. We had discovered the intramolecular coupling reaction of aldehyde imines catalyzed by NHC and had got some preliminary result; We got the esterification products instead of the desired compounds of intramolecular Stetter cyclization.
引文
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