本論文主要分為兩個章節。 第一章為緒論，包括對吲哚和雙吲哚衍生物的介紹以及有關這些雙吲哚衍生物的合成和性質的文獻綜述。並簡要介紹了甲苯磺酰衍生物及其反應。 此外，在第一章末亦揭露了實驗目的和研究目標。

第二章介紹甲苯磺酰腙(N-(烷基)-N-(2 – ((2- 甲苯磺酰肼基)甲基)苯基)苯甲酰胺)在無水四氫呋喃，並在氫化鈉的作用下進行而產生吲哚基吲哚-3-酮衍生物。該反應可能涉及由甲苯磺酰腙在鹼的存在下脫去甲苯磺醯基，產生重氮中間體。接著，重氮中間體脫去氮氣以生成卡賓(carbene)，其插入酰胺的羰基碳中以形成吲哚氧化物，隨後生成吲哚基吲哚-3-一衍生物和3,3-二吲哚衍生物。儘管文獻中已經介紹了相同產物的生成，但是大多數的合成策略都是利用2-取代的吲哚衍生物來作為起始物。在本論文，我們首次使用2-酰基氨基苯甲醛甲苯磺酰腙來構建吲哚基吲哚-3-酮衍生物，並且首次觀察到卡賓可以插入酰胺中的羰基中的反應。

This thesis is divided in two chapters. The first chapter dealt with preface of the thesis which includes the introduction to indole and bis-indole derivatives and literature survey on the synthesis and properties of bis-indole derivatives. In addition, a short introduction on tosyl hydrazone derivatives and their reactions. Further, we then disclosed the aim and research goals at the end of the first chapter.
The second chapter focused on the sodium hydride ( NaH ) mediated reaction of tosylhydrazone(N-(alkyl)-N-(2-((2-tosylhydrazono) methyl) phenyl)benzamide) in dry THF to produce indolylindolin-3-one derivatives. This reaction may be involving the generation of diazo intermediate from the tosylhydrazone by the loss of tosylate in the presence of base. Then the diazo intermediate lose nitrogen to generate carbene, which insert to carbonyl carbon of amide to indole oxide, which subsequently produce indolylindolin-3-one derivative and 3,3'-biindole derivative. Although the same products were reported in the literature, most of them were prepared by using 2-substituted indole derivatives as substrate. Here , for the first time, we utilized 2-acylaminobenzaldehyde tosylhydrazones for the construction of indolylindolin-3-one derivatives and also it is revealed that the insertion of carbene to amidic carbonyl group has been observed herein for the first time.

1. Li, Y-J.; Yan, N.; Liu, C-H.; Yu, Y. and Zhao, Y-L. Org. Lett. 2017, 19, 1160−1163.
2. Wetzel, A.; Gagosz, F. Angew. Chem. Int. Ed. 2011, 50, 7354 –7358.
3. Altinis Kiraz, C. I.; Emge, T. J.; Jimenez, L. S., J. Org. Chem. 2004, 69, 2200–2202.
4. Karadeolian, A.; Kerr, M. A. J. Org. Chem. 2010, 75, 6830–6841.
5. Balogh-Hergovich, E.; Speier, G. J. Mol. Catal. 1989, 57, L9–L12.
6. Zhou, X-Y.; Chen, X.; Wangb L-G.; Yanga, D.; Li, J-H. Synlett 2018, 28, 835–839.
7. Xia, Z.; Hu, J.; Gao, Y-Q.; Yao Q.; Xie, W., Chem. Commun. 2017, 53, 7485—7488.
8. Kumar, C. V. S.; Puranik,V. G. ; Ramana,C. V. Chem. Eur. J. 2012, 18, 9601 – 9611.
9. Ding, X.; Dong, C-L.; Guan, Z.; He, Y-H. Angew. Chem. Int. Ed. 2019, 58, 118 –124.
10. Kaushik, N. K.; Kaushik, N.; Attri, P.; Kumar ,N.; Kim,C. H.; Verma, A. K.; Choi, E. H. Molecules. 2013, 18, 6620-6662.
11. Raihan, M. J.; Kavalar, V.; Kuo, C.-W.; Raju, B. R.; Yao, C.-F., Green Chem. 2010, 12, 1090-1096.