铜和铁促进的烃硫基取代杂环化合物的合成
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摘要
碳-硫键广泛存在于各种天然产物及有机合成分子中,某些烃硫基取代杂环化合物还具有良好的生物活性。因此,发展操作简便、反应条件温和、原料易得、高效高选择性、经济、环境友好的构建这些烃硫基取代碳(杂)环的新方法是有机合成中的重要课题。本论文围绕廉价铜盐和铁盐促进的联硫与官能团化炔烃的亲电环化及其与N-杂环的亲电取代反应,联硫与官能团化偕二卤代烯烃的偶联/环化/(亲电取代)反应展开,目标是合成具有潜在生物活性的新烃硫基取代碳(杂)环化合物和发展合成这些类型有机化合物的新方法,全文主要分六个部分：
1.实现了CuI催化的联硫化合物与邻炔基苯胺的亲电环化反应,以满意的收率得到了3-烃硫基吲哚类化合物,并发现该方法还能扩展到双亲电环化反应,得到桥联烃硫基取代吲哚。通过相关验证实验,提出了可能的反应机理,并阐明了苯硫基铜中间体在所需反应条件下能被空气重新氧化成联硫化合物是实现反应催化循环和提高联硫化合物利用率的关键。
2.研究了CuI催化的联硫化合物与N-杂环sp2C-H键的亲电取代反应,以良好到优秀的收率得到一系列的烃硫基取代N-杂环化合物,为多种类型的烃硫基取代N-杂环化合物的合成提供了一种简便、高效的新方法。反应具有原子经济性好、普适性强、环境友好等特点,同时,还详细考察了反应底物中取代基的电子效应对反应的影响。
3.发展了FeCl3促进的联硫化合物与邻炔基酯的亲电环化反应,高区域选择性地形成4-烃硫基取代异香豆素衍生物.为烃硫基取代异香豆素衍生物合成提供了一种简便的新方法。进一步,发现利用该方法还能高效地一步构建烃硫基取代噻吩并吡喃酮和吲哚并吡喃酬的环骨架。另外,对于双炔基酯,还能发生连续的双环化反应,高选择性地生成3-苯硫基茚叉异苯并呋喃酮化合物,揭示了底物结构对6-endo-dig和5-exo-dig环化反应选择性的影响。此外,对联硫和邻炔基环氧合成3-烃硫基呋喃的反应进行了初探。
4.探索了CuCl2促进的联硫化合物与N,N-二甲基邻炔基苯胺的硫胺化/环化反应,以中等收率得到3-烃硫基吲哚。而当反应体系中不加入联硫化合物时,可以选择性地得到取代的3-氯吲哚和3-溴吲哚化合物。通过Suzuki偶联反应,还研究了3-氯吲哚的衍生化。
5.利用Pd(OAc)2催化的2-(2,2-二溴乙烯基)胺与苯硼酸的偶联/环化反应与CuI催化的吲哚与联硫化合物的亲电取代反应相结合的原理,探索了以2-(2,2-二溴乙烯基)胺为起始原料,合成3-烃硫基吲哚化合物的新途径。
6.探索了CuI催化的联硫化合物与2-(2,2-二溴乙烯基)酚的偶联/环化反应,首次实现了在形成苯并呋喃环过程中同时在2-位引入烃硫基,一步将2个C-Br键分别转化成碳-氧和碳-硫键,为2-烃硫基取代苯并呋喃化合物的合成提供了一种简便的新方法。
Carbon-sulfur bond is displayed in a wide range of natural products and organic molecules. Many sulfenyl-substituted heterocycles exhibit significant biological activities. Therefore, development of new efficient and environmental friendly methods for the synthesis of this class of compounds from readily available starting materials using cheap catalysts is an important goal of organic synthesis. This dissertation focuses on the inexpensive cuprous (cupric) or ferric salts promoted electrophilic cyclization reactions of disulfides with functional alkynes and electrophilic substitution reaction with azaheterocycles, as well as coupling/cyclization/(electrophilic substitution) reaction of disulfides with functional gem-dibromoalkenes. The dissertation is divided into six parts.
1. CuI-catalyzed electrophilic addition/cyclization reaction of2-alkynylanilines with disulfides has been established, which provides a convenient and efficient procedure for the synthesis of3-sulfenylindoles. Moreover, the method proved to be efficient for construction of complex products bearing two attached3-sulfenylindole rings in one-pot process. The present experimental results indicate that both disulfide and the copper catalyst can be reproduced from intermediate phenylthiolate copper under the present conditions in the presence of air.
2. CuI catalvzed efficient and environmentally friendly electrophilic substitution reaction of azaheterocycles with disulfides has been developed for the synthesis of various sulfenyl-substituted azaheterocycles. Morever, the electronic effect of substituents and its impact on the reaction were investigated in detail.
3. FeCl3-promoted electrophilic addition/cyclization reaction of2-alkynylbenzoates with disulfides, which provides a facile and highly regioselective synthetic approach to4-sulfenylisocoumarins. The present procedure is also an efficient approach to thieno-and indol-fused chalcogenylpyrone frameworks. Furthermore, bicyclization product,(E)-3-(2-phenyl-3-(phenyIsulfenyl)inden-1-ylidene)isobenzofuranone, could be achieved via a domino reaction sequence of diynylbenzoate with disulfide. These results disclosed the extraordinary effect of substrates for the6-endo-dig and5-exo-dig annulation. Morever, primary research disclose that3-sulfenylfuran can be synthesized by electrophilic addition/cyclization reaction of2-alkynyloxirane with disulfide.
4. CuCl2promoted sulfoamination/cyclization of N,N-dimethyl-2-alkynylanilines with disulfides has been developed for the synthesis of3-sulfenylindoles. It is found that the haloamination/cyclization products can be selectively obtained without the presence of disulfides in the reaction procedure. In addition, Suzuki-coupling reaction of3-chloroindoles with phenyl boronic acids is carried out.
5. An alternative route to sulfenylindoles is developed by Cul-catalyzed electrophilic substitution of disulfldes with indoles generated in situ by Pd(OAc)2-catalyzed coupling/cyclization of gem-dibromovinylanilines with phenyl boronic acids.
6. Cul-catalyzed coupling/cyclization reaction of gem-dibromovinylphenols with disulfides, which introduction of a sulfenyl functionality at2-position in the formation of benzofurans for the first time. This method provides an efficient and convenient procedure for the formation of2-sulfenylbenzofurans.
1.实现了CuI催化的联硫化合物与邻炔基苯胺的亲电环化反应,以满意的收率得到了3-烃硫基吲哚类化合物,并发现该方法还能扩展到双亲电环化反应,得到桥联烃硫基取代吲哚。通过相关验证实验,提出了可能的反应机理,并阐明了苯硫基铜中间体在所需反应条件下能被空气重新氧化成联硫化合物是实现反应催化循环和提高联硫化合物利用率的关键。
2.研究了CuI催化的联硫化合物与N-杂环sp2C-H键的亲电取代反应,以良好到优秀的收率得到一系列的烃硫基取代N-杂环化合物,为多种类型的烃硫基取代N-杂环化合物的合成提供了一种简便、高效的新方法。反应具有原子经济性好、普适性强、环境友好等特点,同时,还详细考察了反应底物中取代基的电子效应对反应的影响。
3.发展了FeCl3促进的联硫化合物与邻炔基酯的亲电环化反应,高区域选择性地形成4-烃硫基取代异香豆素衍生物.为烃硫基取代异香豆素衍生物合成提供了一种简便的新方法。进一步,发现利用该方法还能高效地一步构建烃硫基取代噻吩并吡喃酮和吲哚并吡喃酬的环骨架。另外,对于双炔基酯,还能发生连续的双环化反应,高选择性地生成3-苯硫基茚叉异苯并呋喃酮化合物,揭示了底物结构对6-endo-dig和5-exo-dig环化反应选择性的影响。此外,对联硫和邻炔基环氧合成3-烃硫基呋喃的反应进行了初探。
4.探索了CuCl2促进的联硫化合物与N,N-二甲基邻炔基苯胺的硫胺化/环化反应,以中等收率得到3-烃硫基吲哚。而当反应体系中不加入联硫化合物时,可以选择性地得到取代的3-氯吲哚和3-溴吲哚化合物。通过Suzuki偶联反应,还研究了3-氯吲哚的衍生化。
5.利用Pd(OAc)2催化的2-(2,2-二溴乙烯基)胺与苯硼酸的偶联/环化反应与CuI催化的吲哚与联硫化合物的亲电取代反应相结合的原理,探索了以2-(2,2-二溴乙烯基)胺为起始原料,合成3-烃硫基吲哚化合物的新途径。
6.探索了CuI催化的联硫化合物与2-(2,2-二溴乙烯基)酚的偶联/环化反应,首次实现了在形成苯并呋喃环过程中同时在2-位引入烃硫基,一步将2个C-Br键分别转化成碳-氧和碳-硫键,为2-烃硫基取代苯并呋喃化合物的合成提供了一种简便的新方法。
Carbon-sulfur bond is displayed in a wide range of natural products and organic molecules. Many sulfenyl-substituted heterocycles exhibit significant biological activities. Therefore, development of new efficient and environmental friendly methods for the synthesis of this class of compounds from readily available starting materials using cheap catalysts is an important goal of organic synthesis. This dissertation focuses on the inexpensive cuprous (cupric) or ferric salts promoted electrophilic cyclization reactions of disulfides with functional alkynes and electrophilic substitution reaction with azaheterocycles, as well as coupling/cyclization/(electrophilic substitution) reaction of disulfides with functional gem-dibromoalkenes. The dissertation is divided into six parts.
1. CuI-catalyzed electrophilic addition/cyclization reaction of2-alkynylanilines with disulfides has been established, which provides a convenient and efficient procedure for the synthesis of3-sulfenylindoles. Moreover, the method proved to be efficient for construction of complex products bearing two attached3-sulfenylindole rings in one-pot process. The present experimental results indicate that both disulfide and the copper catalyst can be reproduced from intermediate phenylthiolate copper under the present conditions in the presence of air.
2. CuI catalvzed efficient and environmentally friendly electrophilic substitution reaction of azaheterocycles with disulfides has been developed for the synthesis of various sulfenyl-substituted azaheterocycles. Morever, the electronic effect of substituents and its impact on the reaction were investigated in detail.
3. FeCl3-promoted electrophilic addition/cyclization reaction of2-alkynylbenzoates with disulfides, which provides a facile and highly regioselective synthetic approach to4-sulfenylisocoumarins. The present procedure is also an efficient approach to thieno-and indol-fused chalcogenylpyrone frameworks. Furthermore, bicyclization product,(E)-3-(2-phenyl-3-(phenyIsulfenyl)inden-1-ylidene)isobenzofuranone, could be achieved via a domino reaction sequence of diynylbenzoate with disulfide. These results disclosed the extraordinary effect of substrates for the6-endo-dig and5-exo-dig annulation. Morever, primary research disclose that3-sulfenylfuran can be synthesized by electrophilic addition/cyclization reaction of2-alkynyloxirane with disulfide.
4. CuCl2promoted sulfoamination/cyclization of N,N-dimethyl-2-alkynylanilines with disulfides has been developed for the synthesis of3-sulfenylindoles. It is found that the haloamination/cyclization products can be selectively obtained without the presence of disulfides in the reaction procedure. In addition, Suzuki-coupling reaction of3-chloroindoles with phenyl boronic acids is carried out.
5. An alternative route to sulfenylindoles is developed by Cul-catalyzed electrophilic substitution of disulfldes with indoles generated in situ by Pd(OAc)2-catalyzed coupling/cyclization of gem-dibromovinylanilines with phenyl boronic acids.
6. Cul-catalyzed coupling/cyclization reaction of gem-dibromovinylphenols with disulfides, which introduction of a sulfenyl functionality at2-position in the formation of benzofurans for the first time. This method provides an efficient and convenient procedure for the formation of2-sulfenylbenzofurans.
引文
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