利用氧化去芳化策略实现多种杂环化合物的合成
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摘要
天然产物中有90%的化合物具备环状结构,其中不少是含有杂原子的杂环化合物,如含氮杂环化合物。因此发展绿色高效的方法来构建含氮杂环化合物具有十分重要的意义。氧化去芳化策略因符合绿色合成的要求而被广泛应用于杂环化合物的合成。但近年来的相关报道都主要集中在酚的氧化去芳化反应研究,对芳胺的氧化去芳化反应研究报道较少。我们课题组以此为切入点,对芳胺的氧化去芳化反应做了一些研究工作,并取得了一定的成果。本论文的主要工作集中于利用氧化去芳化策略合成出多种含氮杂环化合物。
首先,我们发展了一种合成N-杂芳基吲哚衍生物和N-杂芳基苯并咪唑衍生物的方法。在该方法中,我们将2-炔基环己二烯亚胺或2-炔基环己二烯酮与2-炔基芳胺或N1-苄基邻苯二胺反应,通过金属催化的串联反应,最终实现N-杂芳基吲哚衍生物和N-杂芳基苯并咪唑衍生物的合成。该方法底物适用性广,反应条件温和,实验操作简单。
其次,我们利用β-烯胺酯的氧化去芳化策略发展了一种构建indenoazepine衍生物的方法。该方法先将β-烯胺酯进行氧化去芳化反应,随后在碱的催化作用下发生Michael加成反应和串联环化反应,最后通过酸催化的芳构化反应实现indenoazepine衍生物的合成。在探究完机理后,我们发现Michael加成中间体的非芳构化结构很可能是实现7-endo-dig环化的关键。
最后,我们发展了一种从酚或芳胺出发,与2-氨基苯硫酚类化合物反应,利用醋酸碘苯催化的氧化去芳化反应和Cul催化的串联反应合成吩噻嗪衍生物的方法。该反应原料简单、易得,反应过程温和、绿色、经济。
90%of chemicals discovered in nature contain cyclic unit, and many of them are heterocyclic compounds containing a hetero atom, such as N-heterocycles. Thus, the development of efficient methods for the construction of N-heterocycles has attracted continuous interest in organic synthesis. The oxidative dearomatization strategy, which meets the requirement of green synthesis, is widely used in the synthesis of heterocyclic compounds. In recent years, numerous studies focused on on the oxidative dearomatization of phenols, however, little attention was put into the oxidative dearomatization of aromatic amines. For this reason, our group did some research in the field, and obtained certain achievements. In this thesis, the main work is devoted to the synthesis of a variety of N-heterocycles via the oxidative dearomatization strategy.
Firstly, a new strategy for accessing N-heteroarylated indoles and benzimidazoles, which were prepared through metal-catalyzed tandem reactions between2-alkynyl cyclohexadienimines or cyclohexadienones and2-alkynylanilines or N1-benzylbenzene-1,2-diamine, has been developed. The potential of this method is shown by its adaptability to a wide variety of reagents, mild reaction conditions and simple manipulation.
Secondly, a dearomatization strategy of β-enamino esters was developed to construct indenoazepine derivatives. The oxidative dearomatization was combined with a base-promoted tandem Michael addition/polycyclization and an acid-catalyzed aromatization. After exploring the mechanism, we found that the nonaromatic structure of the Michael adducts might be essential to the realization of the7-endo-dig cyclization.
Finally, An alternative approach to prepare phenothiazines through PhI(OAc)2mediated oxidative dearomatization of phenols or anilines and CuI-catalyzed domino reaction with2-aminobenzenethiols is developed. The raw materials are simple and easy to get, the procedure was operated in a mild, green and economic way.
首先,我们发展了一种合成N-杂芳基吲哚衍生物和N-杂芳基苯并咪唑衍生物的方法。在该方法中,我们将2-炔基环己二烯亚胺或2-炔基环己二烯酮与2-炔基芳胺或N1-苄基邻苯二胺反应,通过金属催化的串联反应,最终实现N-杂芳基吲哚衍生物和N-杂芳基苯并咪唑衍生物的合成。该方法底物适用性广,反应条件温和,实验操作简单。
其次,我们利用β-烯胺酯的氧化去芳化策略发展了一种构建indenoazepine衍生物的方法。该方法先将β-烯胺酯进行氧化去芳化反应,随后在碱的催化作用下发生Michael加成反应和串联环化反应,最后通过酸催化的芳构化反应实现indenoazepine衍生物的合成。在探究完机理后,我们发现Michael加成中间体的非芳构化结构很可能是实现7-endo-dig环化的关键。
最后,我们发展了一种从酚或芳胺出发,与2-氨基苯硫酚类化合物反应,利用醋酸碘苯催化的氧化去芳化反应和Cul催化的串联反应合成吩噻嗪衍生物的方法。该反应原料简单、易得,反应过程温和、绿色、经济。
90%of chemicals discovered in nature contain cyclic unit, and many of them are heterocyclic compounds containing a hetero atom, such as N-heterocycles. Thus, the development of efficient methods for the construction of N-heterocycles has attracted continuous interest in organic synthesis. The oxidative dearomatization strategy, which meets the requirement of green synthesis, is widely used in the synthesis of heterocyclic compounds. In recent years, numerous studies focused on on the oxidative dearomatization of phenols, however, little attention was put into the oxidative dearomatization of aromatic amines. For this reason, our group did some research in the field, and obtained certain achievements. In this thesis, the main work is devoted to the synthesis of a variety of N-heterocycles via the oxidative dearomatization strategy.
Firstly, a new strategy for accessing N-heteroarylated indoles and benzimidazoles, which were prepared through metal-catalyzed tandem reactions between2-alkynyl cyclohexadienimines or cyclohexadienones and2-alkynylanilines or N1-benzylbenzene-1,2-diamine, has been developed. The potential of this method is shown by its adaptability to a wide variety of reagents, mild reaction conditions and simple manipulation.
Secondly, a dearomatization strategy of β-enamino esters was developed to construct indenoazepine derivatives. The oxidative dearomatization was combined with a base-promoted tandem Michael addition/polycyclization and an acid-catalyzed aromatization. After exploring the mechanism, we found that the nonaromatic structure of the Michael adducts might be essential to the realization of the7-endo-dig cyclization.
Finally, An alternative approach to prepare phenothiazines through PhI(OAc)2mediated oxidative dearomatization of phenols or anilines and CuI-catalyzed domino reaction with2-aminobenzenethiols is developed. The raw materials are simple and easy to get, the procedure was operated in a mild, green and economic way.
引文
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