端基炔烃参与的若干串联反应与多组分反应研究
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摘要
串联反应与多组分反应是当今有机化学的研究前沿和热点领域之一,在天然产物的全合成、杂环化合物的合成、组合化学等领域具有广泛地应用。本论文系统地研究了端基炔烃参与的一些串联反应与多组分反应,发展了一系列基于此类反应的芳环和杂环化合物的合成新方法。主要内容和结果如下:
1.发展了由磺酰基叠氮与端基炔烃原位产生的N-磺酰基烯酮亚胺与一些同时含有亲电和亲核基团化合物的串联反应:(1)发展了CuI催化的端基炔烃、磺酰基叠氮、水杨醛的三组分反应,该反应提供了一步合成香豆素亚胺衍生物的新方法。将此反应扩展到邻羟基苯乙酮、2-酰基芳胺、2-巯基苯甲醛等底物,发展了多取代的亚胺香豆素、二氢喹啉、硫代苯并吡喃等杂环化合物的合成新方法。(2)发展了CuI催化的端基炔烃、磺酰基叠氮、2-酰基吖丙啶的三组分反应,利用该反应以良好的收率合成了一系列Z-2-磺酰基-5-芳亚苄基-3-吡咯啉类化合物。(3)发展了CuI催化的端基炔烃、磺酰基叠氮、亚胺亚磷的三组分反应,该反应提供了一步合成脒稳定的膦叶立德的新方法。这些新反应和新方法具有快速、高效、通用性好等特点。我们还通过同位素标记等手段,研究了这些串联过程的机理。
2.发现了一种A_3B_2型串联反应:在三乙胺催化下,3分子丙炔酸酯与2分子芳香醛发生串联反应,生成萘的衍生物。这个反应是温度控制的,在-40℃反应3小时后用稀盐酸淬灭反应,反应产物是四氢萘-[2,3-b]-呋喃;在-20℃～-10℃反应5小时,再升温到80℃反应8小时,反应产物是萘乙酸酯类化合物;在-20℃～-10℃反应5小时,再于室温下反应8小时,得到的是两个萘乙醇类非对映异构体,以反式为主。通过这几类化合物之间互相转化的控制实验,以及氘代实验,提出了可能的反应机理。我们还对产物四氢萘-[2,3-b]-呋喃进行了芳构化,得到了具有良好荧光性能的萘并呋喃类化合物,并筛选出了两个具有较高荧光量子收率的化合物。在对这个串联反应进行扩展研究时,发展了三乙胺催化的丙炔酸酯、芳香醛、丁炔二酸二甲酯的三组分反应,该反应提供了一种合成多取代呋喃的新方法。
3.发现了一种E-3-(邻甲酰基芳氧基)-丙烯酸酯和伯胺的串联反应:由水杨醛与丙炔酸酯制备的E-3-(邻甲酰基芳氧基)-丙烯酸酯,在三氟乙酸催化下,与各种伯胺(包括芳香胺和脂肪胺)发生加成-亲核-消除-环化的串联反应,生成1,4-二氢了吡啶。这个方法反应操作简单,收率良好,生成的1,4-二氢吡啶类化合物具有潜在的生物活性,同时还可进一步衍生化。
4.发展了三苯基磷调节的2-酰基吖丙啶与偶氮二甲酸酯的串联反应:三苯基磷与偶氮二甲酸酯原位产生Huisgen阴阳离子,对2-酰基吖丙啶的羰基加成,随后的分子间和分子内的有次序的环化-开环-重排-开环-加成的串联反应,以几乎定量的收率合成了吡唑啉。通过氘代实验结果,提出了这个反应的可能机理。该反应提供了一种合成吡唑啉类化合物高效方法,而所得产物吡唑啉可在甲醇的硫酸液中进一步转化为吡唑类化合物。
5.发展了微波促进的醛、酮、丙二腈的无溶剂三组分反应合成2,6-二氰基苯胺类化合物的新方法。在三乙胺催化和微波的作用下,醛、酮与丙二腈反应,以较高收率合成了2,6-二氰基苯胺类化合物。由于所得产物具有电子受体-给体-受体(A-D-A)结构特性,我们筛选了其中一些化合物的荧光性能,发现三个具有良好荧光性能的化合物。在此基础上,我们还发展了一种聚乙二醇支载的2,6-二氰基苯胺的制备方法。
6.发展了N-芳基酰胺和重氮乙酸乙酯的串联反应合成吲哚类化合物。N-芳基酰胺在2-氯吡啶、2,6-二氯吡啶和Tf_2O的存在下,活化成为两性离子,被具有较强亲核性的重氮乙酸乙酯捕捉,随后的分子内亲电反应-异构化就构建了吲哚。
Domino reactions and Multi-component reactions(MCRs)have been highlighted as one of research frontier,widely used for the construction of heterocycles and in enantioselective synthesis and total synthesis.In this thesis,domino reactions and MCRs involved terminal alkynes are explored for the construction of arens and heterocycles.The discussions and results are listed as following:
1.The N-sulfonyl ketenimine in situ generated by the Copper-catalyzed click reaction of terminal alkynes and sulfonyl azides,undergo a domino intramolecular addition-cyclization-dehydration sequence with special synthons bearing nucleophile and electronphile simultaneously:(a)The copper-catalyzed MCRs of terminal alkynes, sulfonyl azides and salicaldehydes furnish iminocoumarins,and the method is extened to 2-aeylphenols,2-acylanilines,potassium salt of 2-thiobenzaldehyde for the construction of substituted iminocoumarins,iminodihydroquinolines, iminothiochromenes respectively.(b)The copper-catalyzed MCRs of terminal alkynes, sulfonyl azides and 2-acylaziridines furnish Z-5-arylidene-2-imino-3-pyrrolines and the stereochemistry is established by NOESY analysis.(c)The copper-catalyzed MCRs of terminal alkynes,sulfonyl azides and iminophosphoranes are also explored for the synthesis of stabilized phosphorous arnidines.All the methods are general and efficient,while deuterium-labeling experiments are carried out to view the sight of the domino reactions.
2.A TEA-catalyzed domino reaction(A_3B_2)of propiolates(3 equiv.)and benzaldehydes(2 equiv.)are developed.The reaction is temperature dependant:(a) the product is 2,3,9,9a-tetrahydro-naphtha[2,3-b]furan when the reaction is carried out at -40℃for 3h and quenched by 1N HCl.(b)the product is naphthalene when the reaction is carried out at -20～-10℃for 5h and then under reflux for 5h.(c)the product isβ-hydroxyl-naph.thalene when the reaction is carried out at -20～-10℃for 5h and then kept at rt for 5h.The insight of the domino reaction is viewed by the deuterium-labeling reaction and several controlled reactions and a possible mechanism is proposed.Furthermore,2,3,9,9a-tetrahydro-naphtha[2,3-b]furan is aromatized to naphthofuran exhibiting strong fluoresence.The TEA-catalyzed MCRs of propiolates,aryl aldehydes and DMAD for access to furans are also developed and the structure is established by X-ray analysis.The procedure is general and efficient and a possible mechanism is outlined.
3.A novel synthesis of Hantzsch-type N-substituted 1,4-dihydropyridines from salicaldehydes,ethyl propiolate and amines has been developed.Salicaldehydes were treated with ethyl propiolate in the presence of N-methylmorpholine to give ethyl 3-(2-formylphenoxy)-propenoates.Three equiv of ethyl 3-(2-formylphenoxy)-propenoates reacted with one equiv of amines under trifluoroacetic acid(TFA)catalyst to furnish the corresponding N-substituted 1,4-dihydropyridines in good to excellent yields,recovering the starting material salicaldehydes.A possible mechanism for the domino process was proposed. Furthermore,the products can be easily derived via further transformations and three of them exhibited strong fluorescence.
4.A novel,efficient and general domino reaction of 2-acyl-aziridines with the Huisgen zwitterions to furnish 2-pyrazoline rings is described.The Huisgen zwitterion in situ generated by PPh_3 and dialkyl azodicarboxylate is intercepted by 2-acylazridine to undergo a domino reaction for achievement of pyrazoline in quantitative yield,releasing Ph_3PO.The structure is firmly established by X-ray analysis and the deuterium-labeling reactions are carried out.A possible mechanism for the domino sequence is proposed.Furthermore,the resulting pyrazolines are converted to pyrazoles in acidic methanol solution under reflux.
5.A facile parallel synthesis of polysubstituted 2,6-dicyanoanilines via microwave-promoted three-component reaction of aldehydes,ketones and propanedinitrile in solution and also on polymer support(PEG4000)has been developed.The structure of the compound is confirmed by X-ray analysis.The method is general and efficient.The screening for optical properties identified two new compounds with high fluorescence quantum yields.
6.A novel and facile synthesis of indole via domino reaction of N-aryl amide and Ethyl diazoacetate has been established.The structure of the compound is confirmed by X-ray analysis and the methodology could be utilized to indole-fused heteroeyeles preparation.
1.发展了由磺酰基叠氮与端基炔烃原位产生的N-磺酰基烯酮亚胺与一些同时含有亲电和亲核基团化合物的串联反应:(1)发展了CuI催化的端基炔烃、磺酰基叠氮、水杨醛的三组分反应,该反应提供了一步合成香豆素亚胺衍生物的新方法。将此反应扩展到邻羟基苯乙酮、2-酰基芳胺、2-巯基苯甲醛等底物,发展了多取代的亚胺香豆素、二氢喹啉、硫代苯并吡喃等杂环化合物的合成新方法。(2)发展了CuI催化的端基炔烃、磺酰基叠氮、2-酰基吖丙啶的三组分反应,利用该反应以良好的收率合成了一系列Z-2-磺酰基-5-芳亚苄基-3-吡咯啉类化合物。(3)发展了CuI催化的端基炔烃、磺酰基叠氮、亚胺亚磷的三组分反应,该反应提供了一步合成脒稳定的膦叶立德的新方法。这些新反应和新方法具有快速、高效、通用性好等特点。我们还通过同位素标记等手段,研究了这些串联过程的机理。
2.发现了一种A_3B_2型串联反应:在三乙胺催化下,3分子丙炔酸酯与2分子芳香醛发生串联反应,生成萘的衍生物。这个反应是温度控制的,在-40℃反应3小时后用稀盐酸淬灭反应,反应产物是四氢萘-[2,3-b]-呋喃;在-20℃～-10℃反应5小时,再升温到80℃反应8小时,反应产物是萘乙酸酯类化合物;在-20℃～-10℃反应5小时,再于室温下反应8小时,得到的是两个萘乙醇类非对映异构体,以反式为主。通过这几类化合物之间互相转化的控制实验,以及氘代实验,提出了可能的反应机理。我们还对产物四氢萘-[2,3-b]-呋喃进行了芳构化,得到了具有良好荧光性能的萘并呋喃类化合物,并筛选出了两个具有较高荧光量子收率的化合物。在对这个串联反应进行扩展研究时,发展了三乙胺催化的丙炔酸酯、芳香醛、丁炔二酸二甲酯的三组分反应,该反应提供了一种合成多取代呋喃的新方法。
3.发现了一种E-3-(邻甲酰基芳氧基)-丙烯酸酯和伯胺的串联反应:由水杨醛与丙炔酸酯制备的E-3-(邻甲酰基芳氧基)-丙烯酸酯,在三氟乙酸催化下,与各种伯胺(包括芳香胺和脂肪胺)发生加成-亲核-消除-环化的串联反应,生成1,4-二氢了吡啶。这个方法反应操作简单,收率良好,生成的1,4-二氢吡啶类化合物具有潜在的生物活性,同时还可进一步衍生化。
4.发展了三苯基磷调节的2-酰基吖丙啶与偶氮二甲酸酯的串联反应:三苯基磷与偶氮二甲酸酯原位产生Huisgen阴阳离子,对2-酰基吖丙啶的羰基加成,随后的分子间和分子内的有次序的环化-开环-重排-开环-加成的串联反应,以几乎定量的收率合成了吡唑啉。通过氘代实验结果,提出了这个反应的可能机理。该反应提供了一种合成吡唑啉类化合物高效方法,而所得产物吡唑啉可在甲醇的硫酸液中进一步转化为吡唑类化合物。
5.发展了微波促进的醛、酮、丙二腈的无溶剂三组分反应合成2,6-二氰基苯胺类化合物的新方法。在三乙胺催化和微波的作用下,醛、酮与丙二腈反应,以较高收率合成了2,6-二氰基苯胺类化合物。由于所得产物具有电子受体-给体-受体(A-D-A)结构特性,我们筛选了其中一些化合物的荧光性能,发现三个具有良好荧光性能的化合物。在此基础上,我们还发展了一种聚乙二醇支载的2,6-二氰基苯胺的制备方法。
6.发展了N-芳基酰胺和重氮乙酸乙酯的串联反应合成吲哚类化合物。N-芳基酰胺在2-氯吡啶、2,6-二氯吡啶和Tf_2O的存在下,活化成为两性离子,被具有较强亲核性的重氮乙酸乙酯捕捉,随后的分子内亲电反应-异构化就构建了吲哚。
Domino reactions and Multi-component reactions(MCRs)have been highlighted as one of research frontier,widely used for the construction of heterocycles and in enantioselective synthesis and total synthesis.In this thesis,domino reactions and MCRs involved terminal alkynes are explored for the construction of arens and heterocycles.The discussions and results are listed as following:
1.The N-sulfonyl ketenimine in situ generated by the Copper-catalyzed click reaction of terminal alkynes and sulfonyl azides,undergo a domino intramolecular addition-cyclization-dehydration sequence with special synthons bearing nucleophile and electronphile simultaneously:(a)The copper-catalyzed MCRs of terminal alkynes, sulfonyl azides and salicaldehydes furnish iminocoumarins,and the method is extened to 2-aeylphenols,2-acylanilines,potassium salt of 2-thiobenzaldehyde for the construction of substituted iminocoumarins,iminodihydroquinolines, iminothiochromenes respectively.(b)The copper-catalyzed MCRs of terminal alkynes, sulfonyl azides and 2-acylaziridines furnish Z-5-arylidene-2-imino-3-pyrrolines and the stereochemistry is established by NOESY analysis.(c)The copper-catalyzed MCRs of terminal alkynes,sulfonyl azides and iminophosphoranes are also explored for the synthesis of stabilized phosphorous arnidines.All the methods are general and efficient,while deuterium-labeling experiments are carried out to view the sight of the domino reactions.
2.A TEA-catalyzed domino reaction(A_3B_2)of propiolates(3 equiv.)and benzaldehydes(2 equiv.)are developed.The reaction is temperature dependant:(a) the product is 2,3,9,9a-tetrahydro-naphtha[2,3-b]furan when the reaction is carried out at -40℃for 3h and quenched by 1N HCl.(b)the product is naphthalene when the reaction is carried out at -20～-10℃for 5h and then under reflux for 5h.(c)the product isβ-hydroxyl-naph.thalene when the reaction is carried out at -20～-10℃for 5h and then kept at rt for 5h.The insight of the domino reaction is viewed by the deuterium-labeling reaction and several controlled reactions and a possible mechanism is proposed.Furthermore,2,3,9,9a-tetrahydro-naphtha[2,3-b]furan is aromatized to naphthofuran exhibiting strong fluoresence.The TEA-catalyzed MCRs of propiolates,aryl aldehydes and DMAD for access to furans are also developed and the structure is established by X-ray analysis.The procedure is general and efficient and a possible mechanism is outlined.
3.A novel synthesis of Hantzsch-type N-substituted 1,4-dihydropyridines from salicaldehydes,ethyl propiolate and amines has been developed.Salicaldehydes were treated with ethyl propiolate in the presence of N-methylmorpholine to give ethyl 3-(2-formylphenoxy)-propenoates.Three equiv of ethyl 3-(2-formylphenoxy)-propenoates reacted with one equiv of amines under trifluoroacetic acid(TFA)catalyst to furnish the corresponding N-substituted 1,4-dihydropyridines in good to excellent yields,recovering the starting material salicaldehydes.A possible mechanism for the domino process was proposed. Furthermore,the products can be easily derived via further transformations and three of them exhibited strong fluorescence.
4.A novel,efficient and general domino reaction of 2-acyl-aziridines with the Huisgen zwitterions to furnish 2-pyrazoline rings is described.The Huisgen zwitterion in situ generated by PPh_3 and dialkyl azodicarboxylate is intercepted by 2-acylazridine to undergo a domino reaction for achievement of pyrazoline in quantitative yield,releasing Ph_3PO.The structure is firmly established by X-ray analysis and the deuterium-labeling reactions are carried out.A possible mechanism for the domino sequence is proposed.Furthermore,the resulting pyrazolines are converted to pyrazoles in acidic methanol solution under reflux.
5.A facile parallel synthesis of polysubstituted 2,6-dicyanoanilines via microwave-promoted three-component reaction of aldehydes,ketones and propanedinitrile in solution and also on polymer support(PEG4000)has been developed.The structure of the compound is confirmed by X-ray analysis.The method is general and efficient.The screening for optical properties identified two new compounds with high fluorescence quantum yields.
6.A novel and facile synthesis of indole via domino reaction of N-aryl amide and Ethyl diazoacetate has been established.The structure of the compound is confirmed by X-ray analysis and the methodology could be utilized to indole-fused heteroeyeles preparation.
引文
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