由硝基烯合成吲哚、吲哚啉、苯並呋喃及色滿衍生物
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2015
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本論文分為兩個章節，每個章節各自獨立，包含前言、研究目標、實驗結果與討論，以及結論。第壹章節由beta-硝基苯乙烯與芳環在三氯化鋁催化傅-克烷化反應和成硝基烷，經還原胺化之後在溫和條件下以銅試劑催化烏爾曼反應合成3-芳基吲哚，提供一新穎的3-芳基吲哚合成方式。
第貳章節探討beta-硝基苯乙烯的衍生物硝基烯在化學合成上的發展性與應用性，將其作為起始物進行三種化合物的合成。本章節分為三部份，第一部份將溴取代的硝基烯還原成胺類後以烏爾曼反應環化，為2-苄基吲哚啉的合成；第二部份為2-苄基苯並呋喃的合成，將羥取代的硝基烯還原為硝基烷之後，以內夫反應/酸催化合環；第三部份則將羥取代的硝基烯作為中間產物，在鹼催化的條件下行環化加成反應合成2-芳基色滿。
The contents of the thesis is divided into two chapters, each chapter individually including preface, research goal, result and discussion, and conclusion. Chapter I deals with the copper-catalyzed Ullmann reaction to synthesize 3-arylindoles, in which the precursors are furnished by AlCl3-catalyzed Friedel-Crafts alkylation of beta-nitrostyrenes and arenes followed by reduction. Chapter II discuss about the applicability of beta-nitrostyrene derivatives for the synthesis of structurally three types of compounds. The chapter is divided into three parts, first part is about the synthesis of 2-benzylindoline from Ullmann coupling of amines, which are obtained by reduction of 2-bromo-arylsubstituted nitroalkenes. The second part is about synthesis of 2-benzylbenzofurans from nitroalkene derivatives derived from the reduction of 2-hydroxy-arylsubstituted nitroalkenes via Nef reaction. In the last part describes the synthesis of 2-arylchromans derivatives from 2-hydroxy-arylsubstituted nitroalkenes through base mediated intramolecular Michael addition.
The contents of the thesis is divided into two chapters, each chapter individually including preface, research goal, result and discussion, and conclusion. Chapter I deals with the copper-catalyzed Ullmann reaction to synthesize 3-arylindoles, in which the precursors are furnished by AlCl3-catalyzed Friedel-Crafts alkylation of beta-nitrostyrenes and arenes followed by reduction. Chapter II discuss about the applicability of beta-nitrostyrene derivatives for the synthesis of structurally three types of compounds. The chapter is divided into three parts, first part is about the synthesis of 2-benzylindoline from Ullmann coupling of amines, which are obtained by reduction of 2-bromo-arylsubstituted nitroalkenes. The second part is about synthesis of 2-benzylbenzofurans from nitroalkene derivatives derived from the reduction of 2-hydroxy-arylsubstituted nitroalkenes via Nef reaction. In the last part describes the synthesis of 2-arylchromans derivatives from 2-hydroxy-arylsubstituted nitroalkenes through base mediated intramolecular Michael addition.
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3-芳基吲哚, 2-苄基吲哚啉, 2-苄基苯並呋喃, 2-芳基色滿, 硝基烯, 3-arylindole, 2-benzylindoline, 2-benzylbenzofuran, 2-arylchroman, nitroalkene