基于串联反应高效构建稠合吡啶类化合物的应用研究
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摘要
稠合吡啶类化合物是一类重要的具有广泛生物活性的含氮杂环化合物,其合成受到了国内外化学工作者的高度关注。构建稠合吡啶骨架最有效的反应模式之一是串联反应，在合成稠合吡啶衍生物方面显示了独特的优越性。这由于串联反应是将若干单元反应按一定顺序级联反应，避免了中间体的分离和纯化，因此反应高效，已成为构筑各类杂环化合物的有效策略。本论文系统地研究了以具有高反应活性的环1,2-二羰基类化合物及其衍生物为底物，在其它亲核试剂存在下，利用串联反应，高效地合成了一系列结构较为复杂、新颖，部分为原创性母核的稠合吡啶类化合物，体现了反应经济性、合成高效性和环境友好性的特点。本论文研究内容包括以下四个部分：
第一部分我们研究了苊醌、含活泼亚甲基的二芳酰基甲烷和富电子的5-氨基吡唑的三组分串联反应，区域选择性构建了一系列新的多官能化的五环吡唑稠合的萘并异喹啉衍生物。反应操作简便，直接将反应原料在乙酸中回流即可。该扩环反应在无金属催化下将二芳酰基甲烷的活泼亚甲基插入到环戊烯二酮的C(sp2)-C(sp2)键中，以中等以上的产率合成了新的四环产物，同时实现了四个新化学键的构建和两个C-C键的断裂。
第二部分我们研究了以氧气为氧化剂，碘促进的靛红和烯氨酮参与的串联反应构建4,4-二甲基吡咯并[2,3,4-kl]吖啶-1,5-二酮衍生物。该反应经过串联的[3+2]/[4+2]两次环化，原位生成4,4-二甲基-4,5-二氢吡咯并[2,3,4-kl]吖啶中间体，在碘作用下通过单电子氧化得到阳离子自由基，经烯丙基氧化产生最终产物。此外，我们测试了4,4-二甲基吡咯并[2,3,4-kl]吖啶-1,5-二酮衍生物7a-7t (7f除外)具有的对非小细胞肺癌NSCLC(A549)潜在的抗癌生物活性。其中检测到化合物7e的IC50数值与作为参考的标准药物吉非替尼非常接近，显示出良好的抗癌活性，预期可发展成为一种新的先导药物。
第三部分我们研究了碘/氧气协同促进的3-羟基-3-吲哚基-2-吲哚酮衍生物和烯氨酮的串联反应，合成了新的多取代4,5-二甲基吡咯并[2,3,4-kl]吖啶-1(2H)-酮衍生物,产率中等到良好。该反应先经历了分子内环化/开环/再次环化,原位生成4,4-二甲基-4,5-二氢吡咯并[2,3,4-kl]吖啶中间体，随后在碘和氧气的协同作用下形成吖啶阳离子自由基、再发生分子间自由基的捕获、甲基迁移、互变异构及吲哚离去等历程得到最终产物。
第四部分我们研究了碘催化下1-甲基-3-羟基-3-吲哚基-2-吲哚酮和2-羟基-2-吲哚基-1,3-茚二酮衍生物与烯氨酮的[3+3]环加成反应，高效构建功能化的螺二氢咔啉衍生物。当用1-甲基-3-羟基-3-吲哚基-2-吲哚酮与烯氨酮在乙腈中反应合成一系列新的α-咔啉衍生物而用2-羟基-2-吲哚基-1,3-茚二酮与烯氨酮在甲苯中反应则提供了母体结构不同的γ-咔啉衍生物。实验结果表明不同官能化的1-甲基-3-羟基-3-吲哚基-2-吲哚酮和2-羟基-2-吲哚基-1,3-茚二酮衍生物调控了反应的区域选择性。目前为止还没有文献报道利用碘催化的[3+3]环加成反应一步合成咔啉衍生物，并且通过简单的一步操作实现了吲哚的Pictet-Spengler增环反应。
Fused pyridines are a class of important aza-heterocycles with broad biological activity,and their syntheses have been attracted considerable attention from domestic andinternational chemical workers. One of the most efficient methods to construct fusedpyridine skeleton is domino reaction. It shows the unique advantages for the synthesis offused pyridine derivatives. This is because domino reaction is constituted by severalreaction units which run by a cascade sequence, avoiding isolation and purification ofintermediates and maximizing the reaction efficiency. So it has become an efficientstrategy to synthesize all kinds of heterocyclic compounds. In this thesis, highly reactivate1,2-dicarbonyls as reaction substrates were systematically studied to treat with othernucleophiles, and a series of new fused pyridines with more complex structures or partoriginal nucleus were synthesized based on domino reactions. The starting materials havebeen maximized to transform into the desired products, which can embody reactioneconomy, high synthetic efficiency and environmental friendliness. This thesis isconstituted by four parts as follows:
Part I: A series of new and polyfunctionalized pentacyclic pyrazole-fusednaphtho[1,8-fg]isoquinolines were regioselectively synthesized by three-componentreaction of acenaphthylene-1,2-dione with diaroylmethanes and electron-richpyrazol-5-amines in HOAc. The reactions were easy to carry out. During these dominoreaction processes, the ring enlargement under metal-free conditions was readily realizedthrough insertion of active methylene of diaroylmethane into the C(sp2)-C(sp2) bond of thecyclohexa-2,5-dienone ring with the formation of four sigma-bonds and the cleavage oftwo C-C bonds, providing the desired products in moderate yields.
Part II: I2-promoted domino reaction between isatins and enaminones were describedusing molecular O2as an oxidant, and a set of new4,4-dimethylpyrrolo[2,3,4-kl]acridine-1,5(2H,4H)-diones were synthesized through allyloxidation process. The reaction undergoes domino [3+2]/[4+2] bis-cyclizations to yield4,4-dimethyl-4,5-dihydropyrrolo[2,3,4-kl]acridine. Then, a single-electron oxidation ofacridine intermediate generated in situ occurred to give the corresponding acridine radicalcation mediated by molecular I2. The next allyl oxidation generates the corresponding C Hoxidation product. We tested the antitumor activity against lung adenocarcinoma NSCLC(A549) of the pyrrolo[2,3,4-kl]acridine derivatives7a7t (except7f). And compound7eshowed quite good anticancer activity, which is equipotent with Gefitinib. They could beconsidered as new lead compounds for further development.
Part III: I2-promoted domino reaction of3-hydroxyindolin-2-one derivatives withenaminones under O2conditions has been established, providing functionalized4,5-dimethylpyrrolo[2,3,4-kl]acridin-1(2H)-ones derivatives in moderate to good yields.This domino reaction involved an intramolecular cyclization/ring-opening/recyclizationsequence to in situ generated4,4-dimethyl-4,5-dihydropyrrolo[2,3,4-kl]acridin-1(2H)-one,which was further converted into acridine radical cation synergistically promoted bymolecular I2and oxygen. Then acridine radical cation was trapped by iodide radical to giveacridine cation, which underwent methyl migration, tautomerization, and indoleelimination process, generating the thermodynamically stable product.
Part IV: Iodine-catalyzed cascade formal [3+3] cycloaddition reaction betweenindolyl alcohol derivatives and enaminones were developed to construct functionalizedspirodihydrocarbolines. The treatment with a variety of2-hydroxy-2-(1H-indol-3-yl)-1H-indene-1,3(2H)-dione and enaminones gave rise to new γ-carboline products in toluenewhereas α-carboline derivatives were obtained in CH3CN when3-hydroxy-3-(1H-indol-3-yl)-1-methylindolin-2-one was employed in this reaction. Theresults indicated that the difference in the functionalized indolyl alcohol derivatives maycontrol reaction regioselectivities. Importantly, there is no literature dealing with such iodine-catalyzed formal [3+3] cycloaddition for the construction of α-carbolines throughPictet-Spengler annulations of the indole unit in a simple one-step operation.
第一部分我们研究了苊醌、含活泼亚甲基的二芳酰基甲烷和富电子的5-氨基吡唑的三组分串联反应，区域选择性构建了一系列新的多官能化的五环吡唑稠合的萘并异喹啉衍生物。反应操作简便，直接将反应原料在乙酸中回流即可。该扩环反应在无金属催化下将二芳酰基甲烷的活泼亚甲基插入到环戊烯二酮的C(sp2)-C(sp2)键中，以中等以上的产率合成了新的四环产物，同时实现了四个新化学键的构建和两个C-C键的断裂。
第二部分我们研究了以氧气为氧化剂，碘促进的靛红和烯氨酮参与的串联反应构建4,4-二甲基吡咯并[2,3,4-kl]吖啶-1,5-二酮衍生物。该反应经过串联的[3+2]/[4+2]两次环化，原位生成4,4-二甲基-4,5-二氢吡咯并[2,3,4-kl]吖啶中间体，在碘作用下通过单电子氧化得到阳离子自由基，经烯丙基氧化产生最终产物。此外，我们测试了4,4-二甲基吡咯并[2,3,4-kl]吖啶-1,5-二酮衍生物7a-7t (7f除外)具有的对非小细胞肺癌NSCLC(A549)潜在的抗癌生物活性。其中检测到化合物7e的IC50数值与作为参考的标准药物吉非替尼非常接近，显示出良好的抗癌活性，预期可发展成为一种新的先导药物。
第三部分我们研究了碘/氧气协同促进的3-羟基-3-吲哚基-2-吲哚酮衍生物和烯氨酮的串联反应，合成了新的多取代4,5-二甲基吡咯并[2,3,4-kl]吖啶-1(2H)-酮衍生物,产率中等到良好。该反应先经历了分子内环化/开环/再次环化,原位生成4,4-二甲基-4,5-二氢吡咯并[2,3,4-kl]吖啶中间体，随后在碘和氧气的协同作用下形成吖啶阳离子自由基、再发生分子间自由基的捕获、甲基迁移、互变异构及吲哚离去等历程得到最终产物。
第四部分我们研究了碘催化下1-甲基-3-羟基-3-吲哚基-2-吲哚酮和2-羟基-2-吲哚基-1,3-茚二酮衍生物与烯氨酮的[3+3]环加成反应，高效构建功能化的螺二氢咔啉衍生物。当用1-甲基-3-羟基-3-吲哚基-2-吲哚酮与烯氨酮在乙腈中反应合成一系列新的α-咔啉衍生物而用2-羟基-2-吲哚基-1,3-茚二酮与烯氨酮在甲苯中反应则提供了母体结构不同的γ-咔啉衍生物。实验结果表明不同官能化的1-甲基-3-羟基-3-吲哚基-2-吲哚酮和2-羟基-2-吲哚基-1,3-茚二酮衍生物调控了反应的区域选择性。目前为止还没有文献报道利用碘催化的[3+3]环加成反应一步合成咔啉衍生物，并且通过简单的一步操作实现了吲哚的Pictet-Spengler增环反应。
Fused pyridines are a class of important aza-heterocycles with broad biological activity,and their syntheses have been attracted considerable attention from domestic andinternational chemical workers. One of the most efficient methods to construct fusedpyridine skeleton is domino reaction. It shows the unique advantages for the synthesis offused pyridine derivatives. This is because domino reaction is constituted by severalreaction units which run by a cascade sequence, avoiding isolation and purification ofintermediates and maximizing the reaction efficiency. So it has become an efficientstrategy to synthesize all kinds of heterocyclic compounds. In this thesis, highly reactivate1,2-dicarbonyls as reaction substrates were systematically studied to treat with othernucleophiles, and a series of new fused pyridines with more complex structures or partoriginal nucleus were synthesized based on domino reactions. The starting materials havebeen maximized to transform into the desired products, which can embody reactioneconomy, high synthetic efficiency and environmental friendliness. This thesis isconstituted by four parts as follows:
Part I: A series of new and polyfunctionalized pentacyclic pyrazole-fusednaphtho[1,8-fg]isoquinolines were regioselectively synthesized by three-componentreaction of acenaphthylene-1,2-dione with diaroylmethanes and electron-richpyrazol-5-amines in HOAc. The reactions were easy to carry out. During these dominoreaction processes, the ring enlargement under metal-free conditions was readily realizedthrough insertion of active methylene of diaroylmethane into the C(sp2)-C(sp2) bond of thecyclohexa-2,5-dienone ring with the formation of four sigma-bonds and the cleavage oftwo C-C bonds, providing the desired products in moderate yields.
Part II: I2-promoted domino reaction between isatins and enaminones were describedusing molecular O2as an oxidant, and a set of new4,4-dimethylpyrrolo[2,3,4-kl]acridine-1,5(2H,4H)-diones were synthesized through allyloxidation process. The reaction undergoes domino [3+2]/[4+2] bis-cyclizations to yield4,4-dimethyl-4,5-dihydropyrrolo[2,3,4-kl]acridine. Then, a single-electron oxidation ofacridine intermediate generated in situ occurred to give the corresponding acridine radicalcation mediated by molecular I2. The next allyl oxidation generates the corresponding C Hoxidation product. We tested the antitumor activity against lung adenocarcinoma NSCLC(A549) of the pyrrolo[2,3,4-kl]acridine derivatives7a7t (except7f). And compound7eshowed quite good anticancer activity, which is equipotent with Gefitinib. They could beconsidered as new lead compounds for further development.
Part III: I2-promoted domino reaction of3-hydroxyindolin-2-one derivatives withenaminones under O2conditions has been established, providing functionalized4,5-dimethylpyrrolo[2,3,4-kl]acridin-1(2H)-ones derivatives in moderate to good yields.This domino reaction involved an intramolecular cyclization/ring-opening/recyclizationsequence to in situ generated4,4-dimethyl-4,5-dihydropyrrolo[2,3,4-kl]acridin-1(2H)-one,which was further converted into acridine radical cation synergistically promoted bymolecular I2and oxygen. Then acridine radical cation was trapped by iodide radical to giveacridine cation, which underwent methyl migration, tautomerization, and indoleelimination process, generating the thermodynamically stable product.
Part IV: Iodine-catalyzed cascade formal [3+3] cycloaddition reaction betweenindolyl alcohol derivatives and enaminones were developed to construct functionalizedspirodihydrocarbolines. The treatment with a variety of2-hydroxy-2-(1H-indol-3-yl)-1H-indene-1,3(2H)-dione and enaminones gave rise to new γ-carboline products in toluenewhereas α-carboline derivatives were obtained in CH3CN when3-hydroxy-3-(1H-indol-3-yl)-1-methylindolin-2-one was employed in this reaction. Theresults indicated that the difference in the functionalized indolyl alcohol derivatives maycontrol reaction regioselectivities. Importantly, there is no literature dealing with such iodine-catalyzed formal [3+3] cycloaddition for the construction of α-carbolines throughPictet-Spengler annulations of the indole unit in a simple one-step operation.
引文
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