由硝基烯合成吲哚、吲哚啉、苯並呋喃及色滿衍生物

Abstract

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.