臺灣博碩士論文加值系統

本論文分為兩個章節。第一章為緒論，包括對 1,8-萘啶的介紹與其衍生物的合成和性質的文獻回顧。本章節還介紹了有關異吲哚啉1-酮的衍生物、銅催化反應、區域選擇性轉換反應與薗頭反應的文獻回顧。在末尾的部份，我們還敘述了研究目標與動機。
第二章分為兩個部份。第一部份為利用 2-碘苯甲醯胺與 2-溴苯基乙炔進行薗頭偶聯反應，進一步得到相應的亞氨基異吲哚啉-1-酮衍生物，並在後續鈀催化條件下進行赫克反應，分子內合環後得到相應的苯並稠合的異吲哚啉-1-酮衍生物。另一部分為在碳酸銫的鹼性條件下以二甲基亞碸為溶劑，將 2-氨基苯甲醯胺衍生物和 2-炔基芐基氰化物進行銅催化級聯反應得到 1,8-萘啶衍生物，並在碳酸鉀的條件下製備出亞氨基異吲哚衍生物。

This thesis is divided in two chapters. The first chapter dealt with preface of the thesis which includes the introduction to 1,8-naphtharidine derivatives and literature survey on the synthesis and properties of 1,8-
naphtharidine derivatives. In addition, this chapter introduce short literature descriptions about isoindolinone derivatives, copper catalyzed reactions, regioselective-switching reactions and Sonogashira coupling reactions. Further, we then disclosed the aim and research goals at the end of the first chapter.
The second chapter consists two parts. The first part describes about the synthesis of 1,8-naphtharidine derivatives through copper catalyzed tandem cyclization of 2-idobenzamide derivatives and 2-alkynylbenzylcyanides in DMSO using cesium carbonate as base and further the same reaction furnished iminoisoindole derivatives using
potassium carbonate as base.
The next part is Sonogashira coupling reaction of 2-iodobenzamide derivatives and 2-bromophenylacetylenes to obtain corresponding isoindolinone derivatives. The resulted isoindole derivatives further converted into corresponding benzofusedisoindolinone derivatives through
palladium catalyzed Heck coupling.

第壹章、前言 1
一、 金屬串聯反應 2
1. 介紹 2
2. 文獻回顧 3
2-1.串聯反應(Tandem reaction) 3
2-2.格拉澤偶聯反應(Glaser coupling) 4
2-3.烏爾曼反應(Ullman coupling) 4
2-4. Castro-Stephens 偶聯反應 5
2-5. 卡迪奧 - 蕭德凱維奇偶聯反應 (Cadiot-Chokiewicz coupling) 7
2-6.鈴木偶聯反應(Suzuki reaction) 8
2-7.薗頭偶聯反應(Sonogashya reaction) 9
二、 苯乙腈與其相關反應之介紹 10
1. 親核性試劑(Nucleophile) 11
2. 氰化試劑(Cyanating reagent) 12
3. 苯甲醯化試劑(Benzoylating reagent) 13
三、 研究動機與目標 14

第貳章、銅催化合成相關結果 15

一、 菌頭偶聯反應成異吲哚啉-1-酮衍生物 16
1. 相關藥物的介紹 16
2. 文獻回顧 18
3. 反應結果與討論 18
3-1.化合物 3 最佳化條件 18
3-2.化合物 3 反應機構猜測 23
3-3.化合物 4 最佳化條件 24
3-4.化合物 4 反應機構猜測 26
4. 結論 26
5. 參考文獻 27
6. 實驗部分 29
6-1.一般實驗方法 29
6-2. 實驗步驟 31
7. 光譜資料 36

二、 苯並[c,f][1,8]萘啶-5(6H)-酮與亞胺基異吲哚 76
1. 相關藥物介紹 76
2. 文獻回顧 78
3. 結果與討論 79
3-1.最佳化條件篩選 79
3-2.取代基篩選 81
3-3.反應機構探討 87
4. 結論 89
5. 參考文獻 90
6. 實驗部分 91
7. 光譜資料 95

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