缺电子乙烯基环丙烷和甲酰基环丙烷的开环串联反应研究
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摘要
以天然产物为先导开发新药品种是新药创制的一条重要途径。很多具有优秀生物活性的天然产物含有共同的活性骨架(优势结构,活性团等),但结构比较复杂,缺乏高效的有机合成方法来进行构筑,这就在一定程度上限制了从天然产物开发新药先导。因此,开发新的高效构筑复杂分子骨架(Highly EfficientConstruction of Complex Skeletons,HECCS)的方法就显得尤为重要,并逐渐成为当今有机合成化学研究的热点之一,其中,串联反应是最有效的方法之一。
作为现代有机化学中应用较为广泛的3-碳合成子,活化的环丙烷类衍生物的开环反应一直受到人们的普遍关注,并且已经很好地被应用于串联的开环反应来构筑具有复杂结构的有机分子骨架,而在高效构筑复杂分子骨架的策略中,作为5-碳合成子的乙烯基环丙烷在有机合成中的应用潜力还远未被开发,尤其是1,5-亲核开环反应。作为4-碳合成子,甲酰基环丙烷的开环反应研究甚少,近年来,随着氮杂卡宾作为有机催化剂在有机合成中应用越来越广泛,氮杂卡宾催化下活化的甲酰基环丙烷的还原开环酯化及酰胺化反应开拓了甲酰基环丙烷开环反应的新领域,也为我们研究甲酰基环丙烷的开环串联反应提供了很好的思路和依据。
α-亚甲基-γ-丁内酯、香豆素及氢化吡啶并[1,2-α]吲哚骨架广泛存在于天然产物分子中,具有多种生物活性。本文在前人工作的基础上研究了活化的乙烯基环丙烷及双活化甲酰基环丙烷的开环串联反应,并建立了基于环丙烷开环的三种新的有机合成方法,分别得到了含有上述三种分子骨架的三类化合物。
我们设计的活化的乙烯基环丙烷在DABCO·6H_2O作用下通过1,5-方式开环与缺电子芳醛反应得到一系列α-亚甲基-γ-丁内酯类化合物,该反应可能经过了乙烯基环丙烷的亲核开环/与芳醛的Aldol偶联/内酯化三步串联过程。我们还设计研究了氮杂卡宾催化下1,1-双酯基-2-甲酰环丙烷与取代水杨醛及2-氯-1H-吲哚-3-醛的开环串联反应,前者通过串联的环丙烷开环/Knoevenagel缩合反应为大家提供了合成香豆素类化合物的新方法,后者则通过串联的环丙烷开环/酰胺化/环化反应直接构筑了氢化吡啶并[1,2-α]吲哚骨架,为进一步合成含该类环状骨架的天然产物(如:tronocarpine等)及构建基于该类环状骨架的结构多样性分子库提供了潜在的合成策略。
Natural products-based strategy for lead discovery provides an efficient access to new medicines and agrochemicals.Many biologically active natural products have similar skeletons(so-called "privileged structures" or "pharmacophores"),which are difficult to construct efficiently employing current synthetic methods,thus it is very important to develop novel methods and strategies for HECCS(Highly Efficient Construction of Complex Skeletons).Domino reaction is one of the most important and efficient methods for HECCS in contemporary organic synthesis.
As versatile building blocks in modern organic syntheses,activated cyclopropanes have attracted many interests in the field of nucleophilic ring-opening domino reactions.As a 5-carbon synthon,vinylcyclopropanes can undergo nucleophilic ring-opening with 1,3-or 1,5-mode.However,there are very limited reports taking advantage of the 1,5-mode ring-opening by nucleophilic addition which may be selected as a potential candidate to develop new domino reactions for HECCS.In the research of novel carbon-carbon and carbon-heteroatom bonds-forming reactions,N-heterocyclic carbenes(NHCs) have been efficiently applied as organocatalysts in a large number of umpolung chemical transformations. As a 4-carbon synthon,activated formylcyclopropanes can undergo NHC-catalyzed ring-opening based redox esterification and amidation processes,which encourage us to further explore the domino ring-opening reactions of formylcyclopropanes.
We have developed three novel organic synthetic methods based on the domino ring-opening reactions of an activated vinylcyclopropane and di-activated formylcyclopropanes.Firstly,in the presence of DABCO·6H_2O,an activated vinylcyclopropane reacted with substituted benzaldehydes to affordα-methylene-γ-butyrolactones via a 1,5-mode ring opening process.Secondly,NHCs catalyzed the reaction of formylcyclopropane 1,1-diesters with salicylaldehydes via a domino redox esterification/Knoevenagel condensation process to give coumarins in moderate to excellent yields.Thirdly,we have demonstrated a novel domino ring-opening/redox amidation/cyclization reaction between 2-chloro-1H-indole-3- carboaldehydes and formylcyclopropane 1,1-diesters,which provides an efficient and direct access to a 6-5-6 tricyclic hydropyrido[1,2-α]indole skeleton,additionally, this method can be applied for the construction of the tetracyclic core skeleton of the natural product tronocarpine.
作为现代有机化学中应用较为广泛的3-碳合成子,活化的环丙烷类衍生物的开环反应一直受到人们的普遍关注,并且已经很好地被应用于串联的开环反应来构筑具有复杂结构的有机分子骨架,而在高效构筑复杂分子骨架的策略中,作为5-碳合成子的乙烯基环丙烷在有机合成中的应用潜力还远未被开发,尤其是1,5-亲核开环反应。作为4-碳合成子,甲酰基环丙烷的开环反应研究甚少,近年来,随着氮杂卡宾作为有机催化剂在有机合成中应用越来越广泛,氮杂卡宾催化下活化的甲酰基环丙烷的还原开环酯化及酰胺化反应开拓了甲酰基环丙烷开环反应的新领域,也为我们研究甲酰基环丙烷的开环串联反应提供了很好的思路和依据。
α-亚甲基-γ-丁内酯、香豆素及氢化吡啶并[1,2-α]吲哚骨架广泛存在于天然产物分子中,具有多种生物活性。本文在前人工作的基础上研究了活化的乙烯基环丙烷及双活化甲酰基环丙烷的开环串联反应,并建立了基于环丙烷开环的三种新的有机合成方法,分别得到了含有上述三种分子骨架的三类化合物。
我们设计的活化的乙烯基环丙烷在DABCO·6H_2O作用下通过1,5-方式开环与缺电子芳醛反应得到一系列α-亚甲基-γ-丁内酯类化合物,该反应可能经过了乙烯基环丙烷的亲核开环/与芳醛的Aldol偶联/内酯化三步串联过程。我们还设计研究了氮杂卡宾催化下1,1-双酯基-2-甲酰环丙烷与取代水杨醛及2-氯-1H-吲哚-3-醛的开环串联反应,前者通过串联的环丙烷开环/Knoevenagel缩合反应为大家提供了合成香豆素类化合物的新方法,后者则通过串联的环丙烷开环/酰胺化/环化反应直接构筑了氢化吡啶并[1,2-α]吲哚骨架,为进一步合成含该类环状骨架的天然产物(如:tronocarpine等)及构建基于该类环状骨架的结构多样性分子库提供了潜在的合成策略。
Natural products-based strategy for lead discovery provides an efficient access to new medicines and agrochemicals.Many biologically active natural products have similar skeletons(so-called "privileged structures" or "pharmacophores"),which are difficult to construct efficiently employing current synthetic methods,thus it is very important to develop novel methods and strategies for HECCS(Highly Efficient Construction of Complex Skeletons).Domino reaction is one of the most important and efficient methods for HECCS in contemporary organic synthesis.
As versatile building blocks in modern organic syntheses,activated cyclopropanes have attracted many interests in the field of nucleophilic ring-opening domino reactions.As a 5-carbon synthon,vinylcyclopropanes can undergo nucleophilic ring-opening with 1,3-or 1,5-mode.However,there are very limited reports taking advantage of the 1,5-mode ring-opening by nucleophilic addition which may be selected as a potential candidate to develop new domino reactions for HECCS.In the research of novel carbon-carbon and carbon-heteroatom bonds-forming reactions,N-heterocyclic carbenes(NHCs) have been efficiently applied as organocatalysts in a large number of umpolung chemical transformations. As a 4-carbon synthon,activated formylcyclopropanes can undergo NHC-catalyzed ring-opening based redox esterification and amidation processes,which encourage us to further explore the domino ring-opening reactions of formylcyclopropanes.
We have developed three novel organic synthetic methods based on the domino ring-opening reactions of an activated vinylcyclopropane and di-activated formylcyclopropanes.Firstly,in the presence of DABCO·6H_2O,an activated vinylcyclopropane reacted with substituted benzaldehydes to affordα-methylene-γ-butyrolactones via a 1,5-mode ring opening process.Secondly,NHCs catalyzed the reaction of formylcyclopropane 1,1-diesters with salicylaldehydes via a domino redox esterification/Knoevenagel condensation process to give coumarins in moderate to excellent yields.Thirdly,we have demonstrated a novel domino ring-opening/redox amidation/cyclization reaction between 2-chloro-1H-indole-3- carboaldehydes and formylcyclopropane 1,1-diesters,which provides an efficient and direct access to a 6-5-6 tricyclic hydropyrido[1,2-α]indole skeleton,additionally, this method can be applied for the construction of the tetracyclic core skeleton of the natural product tronocarpine.
引文
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