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研究生：	巴朗 Barange Deepak Kumar
論文名稱：	硝基烯與環狀1,3-雙羰基化合物在水的條件下進行反應之探討以及內環磺胺類衍生物之合成 Reactions of nitroalkenes with cyclic 1,3-dicarbonyl compounds under ‘on water’ condition and novel synthesis of fused Sultam derivatives
指導教授：	姚清發 Yao, Ching-Fa
學位類別：	博士 Doctor
系所名稱：	化學系 Department of Chemistry
論文出版年：	2012
畢業學年度：	100
語文別：	英文
論文頁數：	393
中文關鍵詞：	在水的條件、1,3-雙羰基化合物、硝基苯乙烯、[3+2]環加成反應、Suzuki偶聯反應、Heck 偶聯反應、Sonogashira偶聯反應
英文關鍵詞：	"On water", 1,3-dicarbonyl compounds, nitrostyrenes, [3+2]cycloaddition, Suzuki coupling, Heck coupling, Sonogashira coupling
論文種類：	學術論文
相關次數：	點閱：77 下載：2
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本論文主要分為三個章節。在第一章節，主要是分為四個部分，其中A部分是回顧有關於在水的條件下所進行反應之相關文獻報導，在B部分和C部分是描述硝基苯乙烯與環狀1,3-雙羰基化合物在水的條件下進行反應以及內環磺胺類衍生物之合成，C部分則是介紹藉由矽膠在微波條件下進行一鍋化兩步合成以羥基亞胺基二氫苯呋喃類之衍生物。

在第二章節中，介紹藉由過渡金屬催化合成內環磺胺類衍生物以及其多方面的合成應用。在第二章節裡，主要是分為四個部分，其中A部分是回顧有關於合成內環磺胺類衍生物之相關文獻報導，這部分同時也簡要概述有關於三氮唑以往的合成方式和文獻探討。B部分是描述有效率且以一鍋化的方式，藉由銅催化[3+2]環加成反應來合成triazolothiadiazepine-1,1-dioxide之衍生物，以及利用上述的方法合成分別以吲哚啉和噻吩結合內環磺胺類之衍生物。而C部分是介紹一種新穎的合成策略，其藉由溴環化反應來合成出含有雙溴的呋喃結合內環磺胺類之衍生物，而此合成方法也可以應用於合成tetrahydrofuroisoquinolin-5(9bH)-one之衍生物。D部分是探討一種有效率且具有位向選擇性的合成方法，其藉由碘環化反應來合成出4-iodo-2,3-disubstituted-2H-thieno[3,2-e][1,2]thiazine-1,1-dioxide之衍生物。將所得到的產物4-iodo-2,3-disubstituted-2H-thieno [3,2-e] [1,2] thiazine-1,1-dioxide與一系列的硼酸（Suzuki偶聯反應）和活潑烯烴（Heck 偶聯反應）進行偶聯反應。經Sonogashira偶聯反應後的產物可以有效率地合成為疊氮化合物的前驅物，其可以多方面的合成應用於合成出三氮唑結合噻吩和內環磺胺類之衍生物。在第三章節中，主要是收錄整本論文中所有標記的化合物之1H和13C光譜圖以及X光晶體的數據。

The content of this dissertation is divided into three parts. The part I is subdivided into four sections. Section A, illustrate the overview on ‘on water’ reactions and
related literature review. Section B and C describes the ‘on water’ reactions of nitrosytrenes with cyclic 1,3-dicarbonyl compounds and also the synthesis of
hydroxyiminodihydrofuroquinolinone derivatives. Section D deals with one-pot, twostep synthesis of hydroxyiminodihydrobenzofurans mediated by silica gel under
microwave activation condition.
Part II deals with the synthesis of fused sultam derivatives by using transition metal catalysed reactions and their appliation towards diversity oriented synthesis. Part II is subdivided into four sections. Section A, deals with overview, classification and synthetic approaches of fused Sultam derivatives. This section also describe the brief overview on triazole synthesis and literature survey. Section B, describes an efficient and one-pot synthesis of triazolothiadiazepine-1,1-dioxide derivatives via copper
catalyzed tandem [3+2] cycloaddition/N-Arylation and utilization of this method to synthesize indoline and thiophene fused sultam. Section C deals with the novel
synthesis of angular diborminated furosultam derivaitves via bromocyclization strategy. This method is also applicable for the synthesis of tetrahydrofuroisoquinolin-
5(9bH)-one. Section D, demonstrate an efficient and regioselective synthesis of 4-iodo-2,3-disubstituted-2H-thieno[3,2-e][1,2]thiazine-1,1-dioxide derivatives via
iodocyclization approach. The resulting 4-iodo-2,3-disubstituted-2H-thieno[3,2-e][1,2]thiazine-1,1-dioxide utilized to couple with a array of boronic acids (Suzuki
coupling) and activated alkenes (Heck coupling). The Sonogashira coupled product was efficiently transformed to azido precursor, which was exploited for the diversity
oriented synthesis of triazole linked thieno-sultam derivatives.
Part III comprises of 1H and 13C NMR spectral copies and X-Ray crystallograpic data of all the compounds incorporated in this thesis.

Abbreviations                                             i-iv

Abstract                                             v-xiv

Part I
Part I, Section-A: Overview on “on water” reactions and Michael addition
I.A.1 Introduction                                    1

I.A.2 “On water” approaches                                2

I.A.3 Michael addition in the presence of water        16

I.A.4 “On water” Michael addition                            17

I.A.5 References        18

Part I, Section-B: Facile and highly efficient method for the C-alkylation of 2-hydroxy-1,4-naphthoquinones to nitroalkenes under catalyst free ‘on water’ conditions
I.B.1 Introduction                                    23

I.B.2 Review of literature                                24

I.B.3 Results and discussions                                        27

I.B.4 Conclusion                                    32

I.B.5 Experimental Section                                32

I.B.6 References                                    37

Part I, Section-C: Synthesis of C3-nitroalkylated-4-hydroxycoumarin and hydroxyiminodihydrofuroquinolinone derivatives via Michael addition of cyclic 1,3-dicarbonyl compounds to -nitrostyrenes
I.C.1 Introduction                                    40

I.C.2 Review of literature                                42

I.C.3 Results and discussions                                        42

I.C.4 Conclusion                                    52

I.C.5 Experimental Section                                52

I.C.6 References                                    61

Part I, Section-D: A mild and convenient one-pot, two-step synthesis of hydroxyiminodihydrobenzofurans mediated by silica gel under microwave activation conditions
I.D.1 Introduction                                    65

I.D.2 Review of literature                                65

I.D.3 Results and discussions                                67

I.D.4 Conclusion                                    72

I.D.5 Experimental Section                                73

I.D.6 References                                    82

Part II

Part-II, Section-A: Overview on cyclic sulfonamides (Sultam) and triazoles
II.A.1 Introduction                                    85

II.A.2 Synthetic approaches to sultam                        87

II.A.3 Overview on synthesis of triazoles                        97

II.A.4 References                                    100

Part-II, Section-B: One-pot Synthesis of Triazolothiadiazepine-1,1-dioxide Derivatives via Copper Catalyzed Tandem [3+2] Cycloaddition/N-Arylation
II.B.1 Introduction                                    103

II.B.2 Review of literature                                103

II.B.3 Results and discussions                            105

II.B.4 Conclusion                                    112

II.B.5 Experimental Section                                113

II.B.6 References                                    126

Part-II, Section-C: Synthesis of Angular Dibrominated Furosultam Scaffolds via NBS mediated Bromocyclization Strategy
II.C.1 Introduction                                    129

II.C.2 Review of literature                                129

II.C.3 Results and discussions                            130

II.C.4 Conclusion                                    143

II.C.5 Experimental Section                                144

II.C.6 References                                    167

Part-II, Section-D: Regioselective synthesis of 4-iodo-2,3,-disubstituted thiophene fused sultam derivatives via iodocyclization strategy and its application towards triazole linker
II.D.1 Introduction                                    169

II.D.2 Review of literature                                170

II.D.3 Results and Discussions                            170

II.D.4 Conclusion                                    178

II.D.5 Experimental Section                                179

II.C.6 References                                    189

Part-III

III.A.1 X-Ray Crystallographic data                            189

III.B.1 1H and 13C NMR Spectral copies                        206

List of publications                                    393

1. (a) Lindström U. M. Organic reactions in water: Principles, Strategies and Applications Blackwell publishers, New York, 2007; (b) Polshettiwar, V.; Varma, R. S. Acc. Chem. Res. 2008, 41, 629.
2. (a) Breslow, R. Acc. Chem. Res. 1991, 24, 159. (b) Li, C. J.; Chang, T. H. Organic Reactions in Aqueous Media, Wiley, New York, 1997; 7950; (c) Lindström, U. M. Chem. Rev. 2002, 102, 275; (d) Shu, K.; Kei, M. Acc. Chem. Res. 2002, 35, 209; (e) Li, C.-J.; Chem. Rev. 2005, 105, 3095; (f) Pirrung, M. C. Chem. Eur. J. 2006, 12, 1312.
3. (a) Narayan, S.; Muldoon, J. Finn, M. G.; Fokin, V. V.; Kolb, H. C.; Sharpless, K.B. Angew. Chem. Int. Ed. 2005, 44, 3275; (b) Klijin, J. E.; Engberts, J. B. F. N. Nature 2005, 435, 746; (c) Zhang, H. B.; Liu, L.; Chen, Y. J.; Wang, D.; Li, C. -J. Eur. J. Org. Chem. 2006, 869; (d) Price, B. K.; Tour, J. J. Am. Chem. Soc. 2006, 128, 12899; (e) Gonzalez-Cruz, D.; Tejedor, D.; deArmas, P.; Morales, E. Q.; Garcia-Tellado, F. Chem. Commun. 2006, 2798; (f) Gonzsles-Cruz, D.; Tejedor, D.; de Armas, P.; GarcPa-Telaldo, F. Chem. Eur. J. 2007, 13, 4823; (g) Chakraborti, A. K.; Rudrawar, S.; Jadhav, K. B.; Kaur, G.; Chaneshwara, S. V. Green Chem. 2007, 1335; (h) El-Batta, A.; Jiang, C.; Zhao, W.; Anness, R.; Cooksy, A. L.; Bergdahl, M.; J. Org .Chem. 2007, 72, 5244; (i) Huang, J.; Zhang, X.; Armstrong, D. W. Angew. Chem. Int. Ed. 2007, 46, 9073; (j) Guizzetti, S.; Benaglia, M.; Raimondi, L.; Celentano, G. Org. Lett. 2007, 9, 1247; (k) Turner, G. L.; Morris, J. A.; Greaney, M. F. Angew. Chem. Int. Ed. 2007, 46, 7996; (l) Shapiro, N.; Vigalok, A. Angew. Chem. Int. Ed. 2008, 47, 2849; (m) Cozzi, P. G.; Zoli, L. Angew. Chem. Int. Ed. 2008, 47, 4162; (n) Santi, C.; Santoro, S.; Battistelli, B.; Testaferri, L.; Tiecco, M. Eur. J. Org. Chem. 2008, 5387; (o) Wang, F.; Fu, H.; Jiang, Y.; Zhao, Y. Adv. Synth. Catal. 2008, 350, 1830; (p) Zhang, Q. -Y.; Liu, B. -K.; Chen, W.-Q.; Wu, Q.; Lin X.-F. Green Chem. 2008, 972; (q) Pirrung, M. C.; Sarma, K. D.; Wang, J. J. Org. Chem. 2008, 73, 8730.
4. (a) Jeffrey, G.A. An Introduction of Hydrogen Bonding, Oxford University Press, Oxford 1997. (b) Pimentel, G. C.; McLellan, A. L. The Hydrogen Bond, Freeman, San Francisco, 1960; (c) McCauley , J. A.; Navasota , K.; Lander, P. A.; Mischke, S. G.; Semones, M. A. ; Kishi, Y. J. Am. Chem. Soc., 1998, 120 , 7647; (d) Noda, T.; Ishiwata, A.; Uemura, S.; Sakamoto, S.; Hirama, M. Synlett 1998, 298; (e) Noda, T.; Ishiwata, A.; Uemura, S.; Sakamoto, S;. Hirama, M. Synlett 1998 , 298; (f) Satake, M. ; Ofuji, K.; Naoki, H.; James, K. J.; Furey, A.; McMahon, T.; Silke, J.; Yasumoto, T. J. Am. Chem.Soc. 1998, 120 , 9967; (g) Nicolaou, K. C.; Pihko, P. M.; Bernal, F. ; Frederick, M. O.; Qian , W.; Uesaka, N.; Diedrichs, N.; Hinrichs, J.; Koftis, T. V.; Loizidou, E.; Petrovic, G.; Rodriquez, M.; Sarlah, D.; Zou, N. J. Am. Chem. Soc. 2006, 128, 2244. (h) Rigby, J. H.; Maharoof, U. S. M.; Mateo, M. E. J. Am. Chem. Soc. 2000, 122, 6624.
5. (a) Asami, Y.; Kakeya, H.; Onose, R.; Yoshida, A.; Matsuzaki, H.; Osada, H. Org. Lett. 2002, 4, 2845. (b) Allen, J.G.; Danishefsky, S. J. J. Am. Chem. Soc. 2001, 123, 351. (c) White, J. D.; Somers, T. C. J. Am. Chem. Soc., 1994, 116, 9912. (d) Fettes, A.; Carreira, E. M. J. Org. Chem. 2003, 68, 9274. (e) Cook, J. L.; Hunter , C.A.; Low , C. M. R.; Perez-Velasco, A.; Vinter, J. G. Angew. Chem. Int. Ed. 2007, 46, 3706 and references cited therein.
6. Hayashi, Y. Angew. Chem. Int. Ed. 2006, 45, 8103.
7. (a) P. A. Grieco, P. Garner, Z. He, Tetrahedron Lett. 1983, 24, 1897. ; (b) P. A. Grieco, K. Yoshida, P. Garner, J. Org. Chem. 1983, 48, 3137
8. Rideout, D. C.; Breslow, R. J. Am. Chem. Soc. 1980, 102, 7816.
9. Rideout, D. C.; Moitra, U.; Breslow, R. Tetrahedron Lett. 1983, 24, 1901.
10. Blokzijl, W.; Engberts, J. B. F. N. Angew. Chem., Int. Ed. 1993, 32, 1545.
11. Breslow, R. In Structure and Reactivity in Aqueous Solution; Cramer, C. J., Truhlar, D. G., Eds.; American Chemical Society: Washington, DC, 1994; Vol. 568, pp 291-302.
12. Rieber, N., Alberts, J., Lipsky, J. A., Lemal, D. M. J. Am. Chem.Soc. 1969, 91, 5668.
13. Platz, R.; Fuchs, W.; Rieber, N.; Samuel, U.-R.; Jung, J. DE Patent 2615878, 1977.
14. Platz, R.; Fuchs, W.; Rieber, N.; Jung, J. DE Patent 2742034, 1979.
15. Y. Leblanc, R. Zamboni, M. A. Bernstein, J. Org. Chem. 1991, 56, 1971.
16. Kolb, H. C.; Finn, M. G.; Sharpless, K. B. Angew. Chem., Int. Ed. 2001, 40, 2004.
17. Li, Z.; Seo, T. S.; Ju, J. Tetrahedron Lett. 2004, 45, 3143.
18. Butler, R. N.; Coyne, A. G.; Moloney, E. M. Tetrahedron Lett. 2007, 48, 3501.
19. Butler, R. N.; Coyne, A. G.; Cunningham, W. J.; Moloney, E. M.; Burke, L. A. HelV. Chim. Acta 2005, 88, 1611.
20. Gonzalez-Cruz, D.; Tejedor, D.; de Armas, P.; Morales, E. Q.; Garcia-Tellado, F. Chem. Commun. 2006, 2798.
21. Gonzalez-Cruz, D.; Tejedor, D.; de Armas, P.; Garcia-Tellado, F.Chem. Eur. J. 2007, 13, 4823.
22. Bala, K.; Hailes, H. C. Synthesis 2005, 3423.
23. Gajewski, J. J.; Jurayj, J.; Kimbrough, D. R.; Gande, M. E.; Ganem, B.; Carpenter, B. K. J. Am. Chem. Soc. 1987, 109, 1170.
24. Brandes, E.; Grieco, P. A.; Gajewski, J. J. J. Org. Chem. 1989, 54, 515.
25. Demko, Z. P.; Sharpless, K. B. J. Org. Chem. 2001, 66, 7945.
26. Hulme, C. Multicompon. React. 2005, 311.
27. Domling, A. Curr. Opin. Chem. Biol. 2002, 6, 306.
28. Ugi, I.; Werner, B. Methods Reagents Green Chem. 2007, 3.
29. Das Sarma, K.; Pirrung, M. C. J. Am. Chem. Soc. 2004, 126, 444.
30. Pirrung, M. C.; Das Sarma, K. Tetrahedron 2005, 61, 11456.
31. Azizi, N.; Saidi, M. R. Org. Lett. 2005, 7, 3649.
32. Saidi, M. R.; Ziyaei-Halimjani, A. Can. J. Chem. 2006, 84, 1515.
33. Vilotijevic, I.; Jamison, T. F. Science 2007, 317, 1189.
34. Converso, A.; Burow, K.; Marzinzik, A.; Sharpless, K. B.; Finn, M. G. J. Org. Chem. 2001, 66, 4386.
35. Converso, A.; Saaidi, P. L.; Sharpless, K. B.; Finn, M. G. J. Org.Chem. 2004, 69, 7336.
36. Cozzi, P. G.; Zoli, L. Green Chem. 2007, 9, 1292.
37. Cozzi, P. G.; Zoli, L. Angew. Chem., Int. Ed. 2008, 47, 4162.
38. Tandon, V.; Maurya, H. Tetrahedron Lett. 2009, 50, 5896.
39. Rostovtsev, V. V.; Green, L. G.; Fokin, V. V.; Sharpless, K. B. Angew. Chem. Int.Ed. 2002, 41, 2596.
40. Tornøe, C. W.; Christensen, C.; Meldal, M. J. Org. Chem. 2002, 67, 3057.
41. Wei, C.; Li, Z.; Li, C.-J. Synlett 2004, 1472.
42. Wei, C. M.; Li, C. J. J. Am. Chem. Soc. 2002, 124, 5638.
43. Chen, L.; Li, C. J. Chem. Commun. 2004, 2362.
44. Bhattacharya, S.; Sengupta, S. Tetrahedron Lett. 2004, 45, 8733.
45. Churruca, F.; SanMartin, R.; Tellitu, I.; Domı´nguez, E. Synlett 2005, 3116.
46. Ine´s, B.; Moreno, I.; SanMartin, R.; Domı´nguez, E. J. Org. Chem.2008, 73, 8448.
47. Ine´s, B.; SanMartin, R.; Churruca, F. t.; Domı´nguez, E.; Urtiaga, M. K.; Arriortua, M. a. I. Organometallics 2008, 27, 2833.
48. Anderson, K. W.; Buchwald, S. L. Angew. Chem., Int. Ed. 2005, 44, 6173.
49. Guss, C. O.; Rosenthal, R. J. Am. Chem. Soc. 1955, 77, 2549.
50. Podgorsek, A.; Stavber, S.; Zupan, M.; Iskra, J. Green Chem. 2007, 9, 1212.
51. Pravst, I.; Zupan, M.; Stavber, S. Tetrahedron Lett. 2006, 47, 4707.
52. Oshovsky, G.G; Reinhoudt, D.N.; Verboom, W. Angew Chem. Int. Ed. 2007, 46, 2366.
53. (a) List, B. Chem. Rev. 2007, 107, 5413. (b) Dalko, P. I.; Moisan L. Angew. Chem. Int. Ed. 2004, 43, 5138. (c) Enders, D.; Christoph, G.; Hüttl, M. R. M. Angew. Chem. Int. Ed. 2007, 46, 1570. (d) Halland N.; Hansen, T.; Jørgensen, K. A. Angew. Chem. Int. Ed. 2003, 42, 4955
54. Zu, L.; Wang, J.; Wang, W. Org. Lett. 2006, 8, 3077.
55. Zhu, S.; Yu, S.; Ma, D. Angew. Chem. Int. Ed. 2008, 47, 545.
56. (a) R. Ling, U.V.Ekhato, J.R.Rubin, D. J. Wustrow, Tetrahedron 2001, 57, 6579 (b) R. Galeazzi, G. Martelli, G. Mobbili, M. Orena, S. Rinaldi, Tetrahedron : Asymmetry 2003, 14, 3353.
57. (a)Barange, D. K.; Raju, B, R.; Kavala, V.; Kuo, C.-W.; Tu, Y.-C.; Yao, C.-F. Tetrahedron 2010, 66, 3754–3760. (b) Barange, D, K.; Kavala, V.; Kuo, C.-W.; Tseng, C.; Tu, Y.-C.; Yao, C.-F. Tetrahedron Lett. 2009, 50, 5116. (c) Habib, P. M.; Kavala, V.; Raju, B. R.; Kuo, C-W.; Huang, W C.; Yao, C.-F. Eur. J. Org. Chem. 2009, 4503.

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