基于烯酰基乙酰胺的杂环化反应研究
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摘要
传统上讲，杂环化学是有机化学中最大的分支。杂环化合物种类繁多（约占有机化合物总数的一半），广泛应用于医药、农业化学品等方面，并与生命科学、材料科学等密切相关。有关杂环化合物的合成研究在有机合成中占有相当大的比重，文献浩如烟海。杂环化合物，特别是含氮杂环化合物（如生物碱），其广泛的生物活性及结构多样性使其成为主要的合成目标。开拓杂环化合物的合成方法，尤其是简洁、高效、符合原子经济性要求的合成杂环化合物新方法一直令人期待。
在过去的数十年中，α-酰基乙酰胺类化合物作为合成前体已被成功地运用于多取代的杂环化合物的合成中。本论文研究以发现新合成方法为出发点，从易于制备的α-烯酰基乙酰胺类化合物出发，通过串联反应、分子内环合反应及氧化重排反应等合成了几种新颖的杂环结构，包括C2桥连的双杂环化合物，四氢吲哚，哌啶酮，特窗胺及琥珀酰亚胺衍生物。结合实验结果，对反应机理进行了深入细致的研究。
论文共分六个章节。第一章介绍了近年来α-烯酰基乙酰胺在杂环化合物合成研究中的进展；第二章阐述了本论文的选题依据。在第三章中，详细阐述了所发现的一种新合成策略——在温和的条件下，α-烯酰基乙酰胺类化合物和异腈基乙酸乙酯通过串联反应以较高产率生成C2桥连吡咯/噁唑化合物的合成方法。该串联反应涉及两次[3+2]环加成，一步反应即构建了两个不同的杂环，可以很好的区域选择性及非对映选择性一次性构建四个C-C键和一个C-O键。
第四章介绍了一种新颖的串联反应。在温和条件下，α-烯酰基乙酰胺类化合物和异腈基乙酸乙酯反应生成多官能团化的7-氮杂-四氢吲哚类化合物。反应涉及一新颖的反应机理，揭示了异腈基乙酸乙酯中的异氰基碳原子可以作为1,1-双亲电体。
第五章涉及极性反转共轭加成反应的发现，在此基础上提出了一个新的概念。详细描述了远程取代基电性的微妙的变化即可影响共轭加成的区域选择性。这个新的概念有助于加深对共轭加成反应的理解。
第六章，介绍特窗胺在温和的条件下可发生氧化-重排反应生成琥珀酰亚胺衍生物。该反应利用空气中的氧气作为氧化剂，无须渡金属催化或光激发，是一种值得关注的新颖的重排反应。
Traditionally, heterocyclic chemistry is the largest branch in organic chemistry. A widevariety of heterocyclic compounds (about half of the total organic compounds), widely usedin medicine, agricultural chemicals etc., and is closely related to life science and materialscience. Heterocyclic compounds in organic synthesis accounts for a sizeable proportion ofvoluminous literature. Heterocyclic compounds, especially aza-heterocycles (eg alkaloids)posses a wide range of biological activity and structural diversity, making it the main goal ofthe synthesis. Exploring the synthetic methodology of heterocyclic compounds, especially ina simple, efficient, and atom economy fashion, is very desirable.
In the past several decades, α-acyl acetamide compounds have been extensively andsuccessfully used as synthetic precursors for the synthesis of polyfunctionalized heterocycles.The study in this thesis focuses on the discovery of new synthetic methods of the syntheses ofseveral novel heterocycles including two-carbon-tethered heterocyclic pairs,tetrahydroindole,piperidone, tetramic acids and succinimide derivatives by tandem reaction, intramolecularcyclization and oxidative rearrangemen, respectively, starting from the easily availablealkenoyl acetamide derivatives on the other hand, the related reaction mechanisms arediscussed.
The thesis is divided into six chapters. In the first chapter, a review for the research onthe use of alkenoyl acetamide compounds for the synthesis of several heterocyclics in recentyears. And the thesis proposal is presented in chapter two. In chapter three, it is describes thata new strategy for the synthesis of C2-tethered pyrrole/oxazole pairs in good to high yieldsunder mild reaction conditions from alkenoyl acetamides and ethyl isocyanoacetate. Thistandem reaction comprises two [3+2] cycloadditions and allows the construction of twodiferent heterocycles in a single step. This new strategy involves the formation of four C-Cand one C-O bonds in a regio-and diastereoselective manner with the chemoselectivefragmentation.
Chapter four describes a new strategy for the synthesis of various highlyfunctionalized7-aza-tetrahydroindoles from α-alkenoyl acetamide and ethylisocyanoacetate in a single step under mild conditions. A new reaction mechanism isproposed based on the observation that isocyanide carbon plays the role of a1,1-dielectrophile.
Chapter five introduces a new concept, polarity-reversible conjugate addition and showedhow the regioselectivity of a conjugate addition can be reversed with a simple and subtlechange in a remote substituent. This concept provides new insights into the conjugate addition chemistry.
In Chapter six, an oxidative rearrangemen pathway to succinimide derivatives fromtetramic acids is described. This new oxidative rearrangement reaction is unique in severalrespects including the use of triplet oxygen as oxidant without activation (metal-free systemswithout photoexcitation), and it is a noteworthy new tandem reaction.
在过去的数十年中，α-酰基乙酰胺类化合物作为合成前体已被成功地运用于多取代的杂环化合物的合成中。本论文研究以发现新合成方法为出发点，从易于制备的α-烯酰基乙酰胺类化合物出发，通过串联反应、分子内环合反应及氧化重排反应等合成了几种新颖的杂环结构，包括C2桥连的双杂环化合物，四氢吲哚，哌啶酮，特窗胺及琥珀酰亚胺衍生物。结合实验结果，对反应机理进行了深入细致的研究。
论文共分六个章节。第一章介绍了近年来α-烯酰基乙酰胺在杂环化合物合成研究中的进展；第二章阐述了本论文的选题依据。在第三章中，详细阐述了所发现的一种新合成策略——在温和的条件下，α-烯酰基乙酰胺类化合物和异腈基乙酸乙酯通过串联反应以较高产率生成C2桥连吡咯/噁唑化合物的合成方法。该串联反应涉及两次[3+2]环加成，一步反应即构建了两个不同的杂环，可以很好的区域选择性及非对映选择性一次性构建四个C-C键和一个C-O键。
第四章介绍了一种新颖的串联反应。在温和条件下，α-烯酰基乙酰胺类化合物和异腈基乙酸乙酯反应生成多官能团化的7-氮杂-四氢吲哚类化合物。反应涉及一新颖的反应机理，揭示了异腈基乙酸乙酯中的异氰基碳原子可以作为1,1-双亲电体。
第五章涉及极性反转共轭加成反应的发现，在此基础上提出了一个新的概念。详细描述了远程取代基电性的微妙的变化即可影响共轭加成的区域选择性。这个新的概念有助于加深对共轭加成反应的理解。
第六章，介绍特窗胺在温和的条件下可发生氧化-重排反应生成琥珀酰亚胺衍生物。该反应利用空气中的氧气作为氧化剂，无须渡金属催化或光激发，是一种值得关注的新颖的重排反应。
Traditionally, heterocyclic chemistry is the largest branch in organic chemistry. A widevariety of heterocyclic compounds (about half of the total organic compounds), widely usedin medicine, agricultural chemicals etc., and is closely related to life science and materialscience. Heterocyclic compounds in organic synthesis accounts for a sizeable proportion ofvoluminous literature. Heterocyclic compounds, especially aza-heterocycles (eg alkaloids)posses a wide range of biological activity and structural diversity, making it the main goal ofthe synthesis. Exploring the synthetic methodology of heterocyclic compounds, especially ina simple, efficient, and atom economy fashion, is very desirable.
In the past several decades, α-acyl acetamide compounds have been extensively andsuccessfully used as synthetic precursors for the synthesis of polyfunctionalized heterocycles.The study in this thesis focuses on the discovery of new synthetic methods of the syntheses ofseveral novel heterocycles including two-carbon-tethered heterocyclic pairs,tetrahydroindole,piperidone, tetramic acids and succinimide derivatives by tandem reaction, intramolecularcyclization and oxidative rearrangemen, respectively, starting from the easily availablealkenoyl acetamide derivatives on the other hand, the related reaction mechanisms arediscussed.
The thesis is divided into six chapters. In the first chapter, a review for the research onthe use of alkenoyl acetamide compounds for the synthesis of several heterocyclics in recentyears. And the thesis proposal is presented in chapter two. In chapter three, it is describes thata new strategy for the synthesis of C2-tethered pyrrole/oxazole pairs in good to high yieldsunder mild reaction conditions from alkenoyl acetamides and ethyl isocyanoacetate. Thistandem reaction comprises two [3+2] cycloadditions and allows the construction of twodiferent heterocycles in a single step. This new strategy involves the formation of four C-Cand one C-O bonds in a regio-and diastereoselective manner with the chemoselectivefragmentation.
Chapter four describes a new strategy for the synthesis of various highlyfunctionalized7-aza-tetrahydroindoles from α-alkenoyl acetamide and ethylisocyanoacetate in a single step under mild conditions. A new reaction mechanism isproposed based on the observation that isocyanide carbon plays the role of a1,1-dielectrophile.
Chapter five introduces a new concept, polarity-reversible conjugate addition and showedhow the regioselectivity of a conjugate addition can be reversed with a simple and subtlechange in a remote substituent. This concept provides new insights into the conjugate addition chemistry.
In Chapter six, an oxidative rearrangemen pathway to succinimide derivatives fromtetramic acids is described. This new oxidative rearrangement reaction is unique in severalrespects including the use of triplet oxygen as oxidant without activation (metal-free systemswithout photoexcitation), and it is a noteworthy new tandem reaction.
引文
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