壹、三氯化鋁催化分子內SN1反應與氯化生成四氫吡啶[2,1-a]異吲哚酮衍生物貳、微波輔助銅(I)催化三成份串級反應合成氰基吡啶衍生物

Abstract

本篇論文分為兩個獨立章節，每個章節各自包含前言、研究目標、實驗結果與討論以及結論。第一章節為〈三氯化鋁催化分子內SN1反應與氯化生成四氫吡啶[2,1-a]異吲哚酮衍生物〉主要探討了四氫吡啶[2,1-a]異吲哚酮及其衍生物在化學合成上的發展和應用，實驗結果與討論則是將3-羥基-3-呋喃基-N-丁烯基異吲哚啉在酸性催化下生成一穩定的碳陽離子，經由SN1的反應途徑成功合成了四氫吡啶[2,1-a]異吲哚酮衍生物。第二章節為〈微波輔助銅(I)催化三成份串級反應合成氰基吡啶衍生物〉主要介紹了3-氰基吡啶在醫學上的應用以及其合成方法，實驗結果部分則是成功利用微波反應器將3-溴-3-苯基丙烯、3-酮基-3-苯基丙腈和醋酸銨在碘化亞銅的催化下形成產物2,6-二苯基-3-氰基吡啶，同時也對不同官能基受質進行反應產率的測試，都可以得到不錯的結果，可以應用在未來的合成策略當中。The content of the thesis is divided into two chapters, each chapter respectively includes preface, research goal, results and discussion, and conclusion.Chapter I is‘Aluminum Trichloride Catalyzed Chlorinative Intramolecular SN1 Reaction for the Synthesis of Tetrahydropyrido [2,1-a] isoindolones (Valmerins) Derivatives’. We introduce the biological activity and the usage of Valmerins in medicine development. The review on the synthesis of Valmerins derivatives was also included in this chapter. This chapter concludes with the goals and motivation of research topic which is about the SN1 reaction of 3-hydroxy-3-furyl-N-alkenylisoindoline derivatives. The starting materials were synthesized from N-butenyl-2-iodobenzamide derivatives and propargyldiketone compounds in the presence of the copper catalyst, which generated a very stable carbocation after elimination of hydroxyl group. This carbocation intermediate can undergo the SN1 reaction effectively.Chapter II is‘Microwave Assisted Synthesis of Cyanopyridine Derivative via Copper(I) Catalyzed Three-Component Cascade Reaction’. We summarize the synthetic applications, the medicinal properties, and the synthetic method of the cyanopyridine derivatives. The research topic also describes the synthesis of 2,6-aryl-3cyanopyridine derivatives. 3-Bromocinnamaldehyde, 3-oxo-3phenylpropanenitrile and ammonium acetate, undergo a three-component one-pot reaction in the presence of copper catalyst under microwave. The expected products are obtained in high yields, and all of the reactions are clean.