苯乙腈的區域選擇開關反應
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2014
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本論文主要分為兩個章節。第壹章先針對區域選擇開關反應的定義做簡單的介紹，並回顧近年來各種區域選擇開關反應的相關文獻；另外，由於本論文研究主體為苯乙腈的相關研究，亦探討其在反應中可扮演的角色。
第貳章為開關反應之結果與討論。此章節共分為三個部分。第一部分為苯乙腈在強鹼 (叔丁醇鉀)的作用下作為親核性試劑的反應探討，利用碘化亞銅催化由胺基酸酯類合成的鄰碘苯醯胺類與苯乙腈進行反應而合成咪唑啉酮融合異喹啉酮的衍生物。
第二部分為苯乙腈作為氰化試劑的反應探討，利用碘化亞銅催化由胺基酸酯類合成的鄰碘苯醯胺類與苯乙腈進行反應並在弱鹼 (磷酸鉀)的作用下而合成具有生物活性的亞胺基異吲哚啉酮衍生物。
第三部分為苯乙腈作為苯甲醯化試劑的反應探討，此反應透過苯乙腈先作為親核性試劑與苯甲醯胺類起始物反應後再進行縮環，最後合成出在醫療研究上具有潛力的3-羥基-3-取代異吲哚啉酮衍生物。
The thesis is mainly divided into two chapters. The first chapter is the preface of the thesis, which gives a simple introduction of the definition of regioselective switching reaction and the literature review of different regioselective switching reaction in recent years. Moreover, as a result of this thesis’s research emphasis is benzyl cyanide, we also make a brief introduction of its role in various reactions. Then we enclose our research motive and research goals at the end of the first chapter. Chapter II is the results and discussions for the switching reaction. This chapter is subdivided into three parts. The first part is about utilization of benzyl cyanide as a nucleophile. In this part, we synthesized imidazolinone fused isoquinolinone derivatives from the reaction between 2-iodobenzamides derived from amino acid esters and benzyl cyanide by using copper(I) iodide as a catalyst and strong base (potassium tert-butoxide). The second part of Chapter II describes the utilization of benzyl cyanide as a cyanating reagent. In this section, we synthesized the bioactive iminoisoindolinone derivatives from the reaction between 2-iodobenzamides derived from amino acid esters and benzyl cyanide by using copper(I) iodide as a catalyst and mild base (potassium phosphate). The third part of Chapter II deals with the utilization of benzyl cyanide as a benzoylating reagent. In this section, we synthesized 3-hydroxy-3-substituted isoindolinone derivatives from the reaction between 2-iodobenzamides derived from various amines and benzyl cyanide by using copper(I) iodide as a catalyst and cesium carbonate. The product was achieved in two steps.
The thesis is mainly divided into two chapters. The first chapter is the preface of the thesis, which gives a simple introduction of the definition of regioselective switching reaction and the literature review of different regioselective switching reaction in recent years. Moreover, as a result of this thesis’s research emphasis is benzyl cyanide, we also make a brief introduction of its role in various reactions. Then we enclose our research motive and research goals at the end of the first chapter. Chapter II is the results and discussions for the switching reaction. This chapter is subdivided into three parts. The first part is about utilization of benzyl cyanide as a nucleophile. In this part, we synthesized imidazolinone fused isoquinolinone derivatives from the reaction between 2-iodobenzamides derived from amino acid esters and benzyl cyanide by using copper(I) iodide as a catalyst and strong base (potassium tert-butoxide). The second part of Chapter II describes the utilization of benzyl cyanide as a cyanating reagent. In this section, we synthesized the bioactive iminoisoindolinone derivatives from the reaction between 2-iodobenzamides derived from amino acid esters and benzyl cyanide by using copper(I) iodide as a catalyst and mild base (potassium phosphate). The third part of Chapter II deals with the utilization of benzyl cyanide as a benzoylating reagent. In this section, we synthesized 3-hydroxy-3-substituted isoindolinone derivatives from the reaction between 2-iodobenzamides derived from various amines and benzyl cyanide by using copper(I) iodide as a catalyst and cesium carbonate. The product was achieved in two steps.
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區域選擇開關反應, 苯乙腈, 咪唑啉酮融合異喹啉酮衍生物, 亞胺基異吲哚啉酮衍生物, 3-羥基-3-取代異吲哚啉酮衍生物, regioselective switching reaction, benzyl cyanide, imidazolinone fused isoquinolinone derivatives, iminoisoindolinone derivatives, 3-hydroxy-3-substituted isoindolinone derivatives