钯催化合成苯并呋喃和吲哚的研究
摘要
本论文分为两个部分,每部分由两章组成。第一部分是苯并呋哺的合成研究,第二部分是吲哚的合成研究。
第一部分第一章对苯并呋喃类化合物的研究现状进行了较全面的综述并就过渡金属Pd、Cu、Pt、Ru、Rh及其配合物催化合成苯并呋喃的方法进行了阐述,重点介绍了钯催化烯环化、通过Sonogashira偶联反应、钯催化碳酰化环化邻炔酚、及其它钯催化方法构建苯并呋喃。第二章为2-芳基苯并呋喃的合成研究结果。在前人研究基础上,我们采用一锅煮的方法进行苯并呋喃的合成。在得出最佳反应条件后,采用最佳反应条件合成得到了一系列2-芳基取代苯并呋喃化合物。该一锅煮的方法具如使用便宜的试剂,易于处理,不需分离中间体,操作简便的优点。它还能够用于天然产物的合成。
在第二部分第一章里,我们对合成吲哚的各种方法进行了综述。钯催化构建吲哚环的主要方法有:(1)由炔环化构建;(2)烯烃环化构筑吲哚;(3)分子内烯丙基卤芳环偶联环化构筑吲哚;(4)分子内C-N键的构筑方法合成吲哚以及用其它过渡金属催化合成吲哚。在第二章里,我们将合成2-芳基苯并呋喃中所建立起来的一锅法用于吲哚的合成,用最佳的反应条件,成功地采用一锅法得到了2-芳基取代吲哚系列产物。
This dissertation is divided into two parts, each consists of two chapters. Part I describes the studies on the synthesis of benzofurans and part II on the construction of indoles.
The first chapter of part I gives a review to the studies on benzofurans and transition metals, such as Pd, Cu, Pt, Ru, Rh, and their cooperatively catalytical synthesis of benzofurans. It is stressed on the descriptions of palladium catalyzed allyl cyclization, palladium catalyzed Sonogashira coupling, palladium catalyzed carbonylization, cyclization of o-alkyne phenols, and other palladium catalyzed reactions leading to the formation of benzofurans. The second chapter shows the studying results for the synthesis of 2-aryl substituted benzofurans. Based on previous works, a new one-pot protocol to the synthesis of benzofurans was adopted in this paper. The reaction conditions were optimized. A series of 2-aryl substituted benzofurans were synthesized under the optimal reaction conditions. This one-pot process offers advantages like cheap reagents, easily handling, no need for intermeadite isolation, and operational simplicity. It can be used for the preparation of natural products.
The first chapter of part II reviews the researches on the synthesis of indoles. Several approaches to the palladium catalyzed synthesis of indoles are: (1) cyclization of alkyne, (2) cyclization of alkene, (3) cyclization via intramolecular coupling of vinyl halides onto aromatic positions, (4) cyclization via intramolecular C-N bond forming reactions, and other transition metal catalyzed reactions. The second chapter gives applications of the one-pot protocol to the synthesis of 2-aryl benzofuran in the construction of indoles under optimal conditions, Indole products were obtained successfully.
第一部分第一章对苯并呋喃类化合物的研究现状进行了较全面的综述并就过渡金属Pd、Cu、Pt、Ru、Rh及其配合物催化合成苯并呋喃的方法进行了阐述,重点介绍了钯催化烯环化、通过Sonogashira偶联反应、钯催化碳酰化环化邻炔酚、及其它钯催化方法构建苯并呋喃。第二章为2-芳基苯并呋喃的合成研究结果。在前人研究基础上,我们采用一锅煮的方法进行苯并呋喃的合成。在得出最佳反应条件后,采用最佳反应条件合成得到了一系列2-芳基取代苯并呋喃化合物。该一锅煮的方法具如使用便宜的试剂,易于处理,不需分离中间体,操作简便的优点。它还能够用于天然产物的合成。
在第二部分第一章里,我们对合成吲哚的各种方法进行了综述。钯催化构建吲哚环的主要方法有:(1)由炔环化构建;(2)烯烃环化构筑吲哚;(3)分子内烯丙基卤芳环偶联环化构筑吲哚;(4)分子内C-N键的构筑方法合成吲哚以及用其它过渡金属催化合成吲哚。在第二章里,我们将合成2-芳基苯并呋喃中所建立起来的一锅法用于吲哚的合成,用最佳的反应条件,成功地采用一锅法得到了2-芳基取代吲哚系列产物。
This dissertation is divided into two parts, each consists of two chapters. Part I describes the studies on the synthesis of benzofurans and part II on the construction of indoles.
The first chapter of part I gives a review to the studies on benzofurans and transition metals, such as Pd, Cu, Pt, Ru, Rh, and their cooperatively catalytical synthesis of benzofurans. It is stressed on the descriptions of palladium catalyzed allyl cyclization, palladium catalyzed Sonogashira coupling, palladium catalyzed carbonylization, cyclization of o-alkyne phenols, and other palladium catalyzed reactions leading to the formation of benzofurans. The second chapter shows the studying results for the synthesis of 2-aryl substituted benzofurans. Based on previous works, a new one-pot protocol to the synthesis of benzofurans was adopted in this paper. The reaction conditions were optimized. A series of 2-aryl substituted benzofurans were synthesized under the optimal reaction conditions. This one-pot process offers advantages like cheap reagents, easily handling, no need for intermeadite isolation, and operational simplicity. It can be used for the preparation of natural products.
The first chapter of part II reviews the researches on the synthesis of indoles. Several approaches to the palladium catalyzed synthesis of indoles are: (1) cyclization of alkyne, (2) cyclization of alkene, (3) cyclization via intramolecular coupling of vinyl halides onto aromatic positions, (4) cyclization via intramolecular C-N bond forming reactions, and other transition metal catalyzed reactions. The second chapter gives applications of the one-pot protocol to the synthesis of 2-aryl benzofuran in the construction of indoles under optimal conditions, Indole products were obtained successfully.
引文
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