本論文為分為兩個部分。在第一部分是敘述使用(2R,3R,4S)-4-
(1H-3-吲哚基)-2-苯基苯並二氫-3-胺，經由皮克塔-斯賓格勒反應而得到苯並吡喃融合咔唑(benzopyran fused carbazole)衍生物。在合成的過程中，可產生不錯產率的苯並吡喃融合咔唑(benzopyran fused carbazole)及其衍生物。

第二部分則是藉由鈀催化及一鍋化的方式利用薗頭氫炔化串聯反應 (Sonogashira and hydroalkynylation cascade reactions)，來合成4-亞芐基-3,6-二苯基己-2-烯-5-炔醛衍生物。這個特殊的結果顯示反應機構為起始物3-溴-3-苯基丙烯醛加成兩次的炔類，再產生高產率的己-2-烯-5-炔醛衍生物。
此反應中，除了可忍受高官能基外，亦具有簡單而溫和的反應條件是重要的特性。

關鍵字
第一部分:
皮克塔-斯賓格勒反應
苯並吡喃融合咔唑
吡啶並吲哚
色胺
哌啶

第二部分:
鈀催化
薗頭氫炔化串聯反應
薗頭氫炔化串聯反應
茚酮
吡啶
吲哚
咔唑

This thesis consists two parts. In which the first part of thesis describes the preparation of benzopyran fused carbazole derivatives from (2R,3R,4S)-4-(1H-indol-3-yl)-2-phenylchroman-3-amine through Pictet-Spengler reaction. A wide variety of benzopyran fused carbazole derivatives were synthesized in this process in good to moderate yields.

The second part deals with the Pd catalyzed one pot Sonogashira and hydroalkynylation cascade reactions to the synthesis of the 4-benzylidene-3,6-diphenylhex-2-en-5-ynal derivatives. This is an unprecedented result where the addition of two alkyne units to the parent 3-bromo-3-phenylacrylaldehyde to obtain substituted hex-2-en-5-ynal derivatives in good yields. High functional group tolerance, simple and mild reaction conditions are important features in this reaction.

Keyword
Part I:
Pictet-Spengler reaction
Benzopyran fused carbazole
Pyrido indole
Chroman amine
Piperidine

Part II:
Pd catalyzed
Sonogashira and hydroalkynylation cascade reactions
Indenone
Pyridine
Indole
Carbazole

Part I
1. Malhotra, R., Ghosh, R., Dey, T. K., Chakrabarti, S., Ghosh, A., Dutta, S., Asijaa, S., Roy, S., Dutta, S., Basu, S. Hajra, S. Eur. J. Org. Chem. 2013, 772-780.
2. Batsomboon, P.; Phakhodee, W.; Ruchirawat, S.; Ploypradith, P. J. Org.Chem. 2009, 74, 2009-4012.
3. Zhu, H.-L.; Ling, J.-B.; Xu, P.-F. J. Org. Chem. 2012, 77, 7737-7743.
4. Logers, M.; Overman, L. E.; Welmaker, G. S. J. Am. Chem. Soc. 1995, 117, 9139-9150.
5. Li, J.; Wang, T.; Yu, P.; Peterson, A.; Weber, R.; Soerens, D.; Grubisha, D.; Bennett, D.; Cook, J. M. J. Am. Chem. Soc. 1999, 121, 6998-7010.
6. Komnatnyy, V. V.; Givskov, M.; Nielsen, T. E. Chem. Eur. J. 2012, 18, 16793-16800.
7. Klohs, M. W.; Draper, M. D.; Keller, F.; Malesh, W.; Petracek, F. J. J. Am. Chem. Soc. 1954, 76, 1332-1334.
8. Starr, R. I.; Timm, R. W.; Doxtader, K. G.; Hurlbut, D. B.; Volz, S. A.; Goodall, M. J. Agric. Food Chem. 1996, 44, 1603-1608.
9. Kelly, K. L.; Johnston, J. J. J. Agric. Food Chem. 1995, 43, 1208-1211
10. Barker, T. J.; Duncan, K. K.; Otrubova, K.; Boger, D. L. ACS Med. Chem. Lett. 2013, 4, 985-988.
11. Ishikawa, H.;Colby, D. A.; Boger, D. L. J. Am. Chem. Soc. 2008, 130, 420-421.
12. Kato, J.; Li, Y.; Xiao, K.; Lee, J. S.; Luo, J.; Tuscano, J. M.; O’Donnell, R. T.; Lam, K. S.; Mol. Pharmaceutics. 2012, 9, 1727-1735.
13. Stöckigt, J.; Antonchick, A. P.; Wu, F.; Waldmann, H. Angew. Chem. 2011, 123, 8692-8719.
14. Yu, S.; Berner, O. M.; Cook, J. M. J. Am. Chem. Soc. 2000, 122, 7827-7828.
15. Martin, S. F.; Chen, K. X.; Eary, C. T. Org. Lett. 1999, 1, 79-81.
16. Fang, H.; Wu, X.; Nie, L.; Dai, X.; Chen, J.; Cao, W.; Zhao, G. Org. Lett. 2010, 12, 5366-5369.
17. Trzupek, J. D.; Lee, D.; Crowley, B. M.; Marathias, V. M.; Danishefsky, S. J. J. Am. Chem. Soc. 2010, 132, 8506-8512
18. Pictet, A.; Spengler, T. Ber. Dtsch. Chem. Ges. 1911, 44, 2030-2036.
19. Larghi, E. L.; Kaufman, T. S. Eur. J. Org. Chem. 2011, 5195-5231.
20. Lee, Y.; Klausen, R. S.; Jacobsen, E. N. Org. Lett. 2011, 13, 5564-5567.
21. Liu, J.-T.; Yao, C.-F. Tetrahedron Lett. 2001, 42, 6147-6150.
22. Yan, M.-C.; Jang, Y.-J.; Kuo, W.-Y.; Tu, Z.; Shen, K.-H.; Cuo, T.-S.; Ueng, C.-H.; Yao, C.-F. Hetecycles 2002, 57, 1033-1048.
23. Habib, P. M.; Kavala, V.; Kuo, C.-W.; Raihan, M.-J.; Yao, C.-F. Tetrahedron Lett. 2010, 66, 7050-7056.
24. Nose, A.; Kudo, T. Chem. Pharm. Bull. 1981, 29, 1159-1161.
25. Zhou, Y.; Li, J.; Liu, H.; Zhao, L.; Jiang, H. Tetrahedron Lett. 2006, 47, 8511-8514.
26. Ramesh, C.; Kavala, V.; Kuo, C.-W.; Raihan, M.-J.; Raju, B. R.; Yao, C.-F. Eur. J. Org. Chem. 2010, 3796-3801.
27. Prajapati, D.; Gohain, M. Synth. Commun. 2008, 38, 4426-4433.
28. Herrera, R. P.; Sgarzani, V.; Bernardi, L.; Ricci, A. Angew. Chem. 2005, 44, 6576-6579.
29. Awuah, E.; Capretta, A. J. Org. Chem. 2010, 75, 5627-5634.
30. Seayad, J.; Seayad, A. M.; List, B. J. Am. Chem. Soc. 2006, 128, 1086-1087.
31. Gremmen, C.; Wanner, M. J.; Koomen, G.-J. Tetrahedron Lett. 2001, 42, 8885-8888.
32. Sadanandam, P.; Sathaiah, N.; Jyothi, V.; Chari, M. A.; Shobha, D.; Das, P.; Mukkanti, K. Lett. Org. Chem. 2012, 9, 683-690.
Part II
1. Eckhardt, M.; Fu, G. C. J. Am. Chem. Soc. 2003, 125, 13642-13643.
2. Heck, R. F.; Nolley, J. P. J. Org .Chem. 1972, 37, 2320-2322.
3. King, A. O.; Okukado, N.; Negishi, E.-I. J. Chem. Soc. 1977, 683-684.
4. Miyaura, N.; Suzuki, A. J. Chem. Soc. 1979, 866-687.
5. Herndon, J. W.; Zhu, J.; Sampedro, D. Tetrahedron Lett. 2000, 56, 4985-4993.
6. Jana, R.; Paul, S.; Biswas, A.; Ray, J. K. Tetrahedron Lett. 2010, 51, 273-276.
7. Mahendar, L.; Satyanarayana, G. J. Org. Chem. 2014, 79, 2059-2074.
8. Isogai, Y.; Menggenbateer, F.; Khan, N.; Asao, N. Tetrahedron Lett. 2009, 65, 9575-9582.
9. Pünner, F.; Hilt, G. Top. Comm. Chem. 2012, 3617-3619.
10. Sonogashira, K. J. Organomet. Chem. 2002, 653, 46-49.
11. Vechorkin, O.; Barmaz, D.; Proust, V.; Hu, X. J. Am. Chem. Soc. 2009, 131, 12078-12079.
12. King, A. O.; Yasuda, N. Topics Organomet. Chem. 2004, 6, 205-245.
13. Chinchilla, R.; Najera, C. Chem. Rev. 2007, 107, 874-922.
14. Breuer, S. W. J. Labelled Cpd. Radiopharm. 2000, 43, 283-286.
15. Wang, G.; Chen, X.; Miao, G.; Yao, W; Ma, C. J. Org. Chem. 2013, 78, 6223-6232.
16. Liang, Y.; Xie, Y.-X.; Li, J.-H. J. Org. Chem. 2006, 71, 379-381.
17. Gawande, S. C.; Kavala, V.; Zanwar, M. R.; Kuo, C.-W.; Huang, H. -N.; He, C.-H.; Kuo, T.-S.;Yao, C.-F. Adv. Synth. Catal. 2013, 355, 3022-3036.