Title

利用氯化銅進行三步一鍋化合成苯並[b]呋喃的衍生物並應用於抗菌分子合成之研究

Translated Titles

The study in copper(II) chloride-mediated one pot three-step syntheses of benzo[b]furan derivatives and its application for the total synthesis of antimicrobial molecular

DOI

10.6845/NCHU.2012.00785

Authors

劉健良

Key Words

三步一鍋化 ; 苯並[b]呋喃 ; one pot three-step ; benzo[b]furan

PublicationName

中興大學化學系所學位論文

Volume or Term/Year and Month of Publication

2012年

Academic Degree Category

碩士

Advisor

陳耀鐘

Content Language

繁體中文

Chinese Abstract

我們成功地使用氯化銅作為金屬媒介,並且應用在三步一鍋化合成苯並[b]呋喃的衍生物,不使用鈀金屬和配位基催化的耦合反應條件,不但有便宜和容易從產物中移除的優點,而且可以得到好的總產率。 本實驗室開發的三步一鍋化反應,成功應用於抗菌分子之合成,合成的過程有6個步驟,起始物使用4-甲基苯甲醚,經過碘化反應,得到化合物28,接著利用氯化銅催化進行三步一鍋化反應,得到化合物63,最後經過格林納加成反應、水解反應,得到抗菌分子23。

English Abstract

Copper(II) chloride has been successfully used as the medium to one-pot three-steps synthesis of benzo[b]furan derivatives. A palladium-free and ligand-free reaction condition for Sonogashira- type coupling has been developed, this catalytic system is cheap and easily removed, and provide a good yield. Total synthesis of antimicrobial molecule was accomplished in six steps. This novel route was starting from the 4-methylanisole 64. The iodination of compound 64 by treating with NIS in the presence of TMSCl can provide the 90% yield. After the copper(II) chloride promoted one-pot three-step reactions of iodoanisole 28 as the key step for the construction of benzo[b]furan skeleton 63, the further steps were carried out through Grignard reagent addition and hydrolysis reaction to afford the antimicrobial molecule.

Topic Category 基礎與應用科學 > 化學
理學院 > 化學系所
Reference
  1. 2. Razzuk, A.; Biehl, E. R. J. Org. Chem. 1987, 52, 2619-2622.
    連結:
  2. 3. Mitchell, H.; Leblanc, Y. J. Org. Chem. 1994, 59, 682-687
    連結:
  3. 5. Beletskaya, I. P.; Cheprakov, A. V. Coord. Chem. Rev. 2004, 248, 2337.
    連結:
  4. 6. Kohei, T.; Miyaura, N. Topic in Current Chemistry, 2002, 219, 1-9.
    連結:
  5. 7. Agrofoglio, L. A.; Gillaizeau, I.; Saito, Y. Chem. Rev. 2003, 103, 1875.
    連結:
  6. 11. Heck, R. F. J. Am. Chem. Soc. 1968, 90, 5518.
    連結:
  7. 12. Nicolaou, K. C.; Bulger, P. G.; Sarlah, D. Angew. Chem. Int. Ed. 2005, 44, 442.
    連結:
  8. 14. Muci, A. R.; Buchwald, S. L. Topic in Current Chemistry, 2002, 219, 131-209.
    連結:
  9. 18. Kelkar, A. A.; Patil, N. M.; Chaudhari, R. V. Tetrahedron Letters 2002 ,43, 7143.
    連結:
  10. 19. Klapars, A.; Huang, X.; Buchwald, S. L. J. Am. Chem. Soc. 2002, 124, 7421.
    連結:
  11. 21. Goldberg, I. Chem. Ber. 1906, 39, 1691.
    連結:
  12. 22. Hurtley, W. R. H. J. Chem. Soc. 1929, 1870
    連結:
  13. 23. (a) Klapars, A.; Huang, X.; Buchwald, S. L. J. Am. Chem. Soc. 2002, 124, 7421. (b) Antilla, T.; Klapars, A.; Buchwald, S. L. J. Am. Chem. Soc. 2002, 124, 11684. (c) Klapars, A.; Antilla, J. C.; Huang, X.; Buchwald, S. L. J. Am. Chem. Soc. 2001, 123, 7727.
    連結:
  14. 25. Kienle, M.; Dubbaka, S.; R.; Brade, K.; Knochel, P. Eur. J. Org. Chem. 2007, 4166.
    連結:
  15. 33. Stephens, R. D.; Castro, C. E. J. Org. Chem. 1963, 28, 3313.
    連結:
  16. 34. Dieck, H. A.; Heck, F. R. J. Organomet. Chem. 1975, 93, 259.
    連結:
  17. 35. Cassar, L. J. Organomet. Chem. 1975, 93, 253
    連結:
  18. 36. Sonogashira, K.; Tohda, Y.; Hagihara, N. Tetrahedron Lett. 1975, 16, 4467.
    連結:
  19. 38. Chinchilla, R.; Najera, C. Chem. Rev. 2007, 107, 874.
    連結:
  20. 44. (a) Electronic Materials: The Oligomer Approach; Mullen, K.,
    連結:
  21. 47. Keith, B.; Sinan, B. J. Chem. Soc., Perkin Trans. 2, 1998, 1603.
    連結:
  22. 48. Barton, T. J.; Groh, B. L. J. Org. Chem. 1985, 50, 158.
    連結:
  23. 62. Zanon, J.; Klapars, A.; Buchwald, S. L. J. Am. Chem. Soc. 2003, 125, 2890.
    連結:
  24. 63. Cristau, H. J.; Ouali, A.; Spindler, J. F.; Taillefer, M. Chem. Eur. J. 2005, 11, 2483.
    連結:
  25. 64. Schareina, T.; Zapf, A.; Magerlein, W.; Muller, N.; Beller, M. Chem. Eur. J. 2007, 13, 6249.
    連結:
  26. 67. Pahari, P.; Rohr, J. J. Org. Chem. 2009, 74, 2750.
    連結:
  27. 68. (a) Singh, B. N. Antiarrhythmic actions of amiodarone: A profile of a paradoxical agent. Am. J. Cardiol. 1996, 78, 41. (b) Carlsson, B.; Singh, B. N.; Temciuc, M.; Nilsson, S.; Li, Y. L.; Mellin, C.; Malm, J. J. Med. Chem. 2002, 45, 623.
    連結:
  28. Phytochemistry 2001, 57, 437.
    連結:
  29. 73. (a) Day, S. H.; Chiu, N. Y.; Tsao, L. T.; Wang, J. P.; Lin, C. N.
    連結:
  30. Souza, G. E. P.; Lopes, N. P. Phytochemistry 2000, 55, 809.
    連結:
  31. 78. Henke, A.; Srogl, J. Chem. Commun. 2010, 46, 6819.
    連結:
  32. 1. (a) Ma, D.; Liu, F. Chem. Commun. 2004, 1934. (b) Takimiya, K.; Ebata, H.; Miyazaki, E.; Yamamoto, T. Org. Lett. 2009, 9, 4499. (c) Dymock, B. W.; Kocienski, P. J.; Pons, J.-M. Synthesis 1998, 1655
  33. 4. Ma, D.; Xia, C.; Jiang, J.; Zhang, J.; Tang, W. J. Org. Chem. 2003, 68, 442.
  34. 8. (a) Sonogashira, K.; Tohda, Y.; Hagihara, N. Tetrahedron Lett. 1975, 16, 4467. (b) Takahashi, S.; Kuroyama, Y.; Sonogashira, K.; Hagihara, N. Synthesis 1980, 627. (c) Cassar, L. J. Organomet. Chem. 1975, 93, 253. (d) Dieck, H. A.; Heck, R. F. J. Organomet. Chem. 1975, 93, 259.
  35. 9. (a) Mitchell, T. N. Synthesis 1992, 803. (b) Kosugi, M.; Sasazawa, K.; Shimuzi, Y.; Migita, T. Chem. Lett. 1977, 301. (c) Scott, W. J.; Stille, J. K. J. Am. Chem. Soc. 1986, 108, 3033. (d) Piers, E.; Friesen, R. W.; Keay, B. A. Tetrahedron 1991, 47, 4555.
  36. 10. (a) Miyaura, N., Suzuki, A. Chem. Rev. 1995, 95, 2457. (b) Snieckus, V. Chem. Rev. 1990, 90, 879. (c) Matteson, D. S. Tetrahedron 1989, 45, 1859. (d) Miyaura, N.; Yamada, K.; Suzuki, A. Tetrahedron Lett. 1979, 20, 3437. (e) Miyaura, N.; Sato, M.; Suzuki, A. Tetrahedron Lett. 1986, 27, 3745.
  37. 13. (a) Trost, B. M.; Fullerton, T. J. J. Am. Chem. Soc. 1973, 95, 292. (b) Trost, B. M.; Dietsch, T. J. J. Am. Chem. Soc. 1973, 95, 8200. (c) Trost, B. M.; Strege, P. E. J. Am. Chem. Soc. 1977, 99, 1649. (d) Trost, B. M.; Crawley, M. L. Chem. Rev. 2004, 103, 2921
  38. 15. Guram, A. S.; Rennels, R. A.; Buchwald, S. L. Angew. Chem. Int. Ed. 1995, 34, 3609.
  39. 16. Meyers, C.; Maes, Bert U. W.; Loones, Kristof T. J.; Bal, G.; Guy, L. F.; Dommisse, R. A J. Org. Chem. 2004, 69, 6010.
  40. 17. (a) Deng, W; Wang, Y. F.; Zou, Y.; Liu, L. Guo, Q. X. Tetrahedron Letter,2004, 45, 2311.; (b) Klapars, A.; Huang, X.; Buchwald, S.L. J. Am. Chem. Soc., 2002, 124, 7421.; (c) Antilla, J. C.; Klapars, A.; Buchwald, S.L. J. Am. Chem. Soc., 2002, 124, 11684.; (d) Deng, W; Wang, Y. F.; Zou, Y.; Liu, L. Guo, Q. X. Synlett, 2004, 6010.
  41. 20. (a) Ullmann, F. Ber. Dtsch. Chem. Ges. 1903, 36, 2382. (b) Ullmann, F.; Bielecki, J. Ber. Dtsch. Chem. Ges. 1901, 34, 2174.
  42. 24. (a) Evano, G.; Blanchard, N.; Toumi, M. Chem. Rev. 2008, 108, 3054. (b) Gujadhur, R. K.; Bates, C. G.; Venkataraman, D. Org. Lett. 2001, 3, 4315. (c) Allred, G. D.; Liebeskind, L. S. J. Am. Chem. Soc. 1996, 118, 2748. (d) Xie, X.; Cai, G.; Ma, D. Org. Lett. 2005, 7, 4693. (e) Chen, Y. J.; Chen, H. H. Org. Lett. 2006, 8, 5609.
  43. 26. (a) Gujadhur, R.; Venkataraman, D. Synth. Commun. 2001, 38, 2865. (b) Jiang, Y.; Wu, N.; Wu, H.; He, M. Synlett. 2005, 2731. (c) Pei, L.; Qian,W. Synlett. 2006, 1719.
  44. 27. (a) 黃華民論文, 2008, 國立中興大學陳耀鐘老師實驗室 (b)陳鴻志論文, 2009, 國立中興大學陳耀鐘老師實驗室 (c) 胡世憲論文, 2009, 國立中興大學陳耀鐘老師實驗室。
  45. 28. Zhang, S. L.; Liu, L.; Fu, Y.; Guo, Q. X. Organometallics 2007, 26, 4546.
  46. 29. (a) Klapars, A.; Antilla, J. C.; Huang, X.; Buchwald, S. L. J. Am. Chem. Soc. 2001, 123, 7727. (b) Leeuwena, PietW. N. M. van.; Strijdonck, Gino P. F. van. Tetrahedron Letters , 2005, 46, 2405. (c) Ma, D.; Cai, Q.; Zhang, H. Org. Lett. 2003, 5, 3799. (d) Antilla, J. C.; Baskin, J. C. M.; Barder, T. E.; Buchwald, S. L. J. Org. Chem. 2004, 69, 5578. (e) Kunz, K.; Scholz, U.; Ganzer, D. Synlett 2003, 2428.
  47. 30. Cristau, H. J.; Cellier, P. P.; Spindler, J. F.; Taillefer, M. Chem. Eur. J. 2004, 10, 5607.
  48. 31. (a)Gujadhur, R. K; Bates, C. G.; Venkataraman, D. Org. Lett., 2001, 3, 4315. (b) Pu, Y.-M.; Ku, Y.-Y.; Grieme, T.; Henry, R.; Bhatia, A. V. Tetrahedron Lett. 2006, 47, 149. (c) Allred, G. D.; Liebeskind, L. S. J. Am. Chem. Soc. 1996, 118, 2748.
  49. 32. (a) Xin, L.; Weiliang, B. J. Org. Chem. 2007, 72, 3863. (b) Kwong, Y. F.; Klapars, A.; Buchwald, S. L. Org. Lett. 2002, 4, 3517. (c) Kwong, Y. F.; Klapars, A.; Buchwald, S. L. Org. Lett. 2002, 4, 581. (d) Monnier, F.; Turtaut, F.; Duroure, L.; Taillefer, M. Org. Lett.2008, 10, 3203.
  50. 37. (a) Siemsen, P.; Livingston, R. C.; Diederich, F. Angew. Chem. Int. Ed. 2000, 39, 2632. (b) Hay, A. S. J. Org. Chem. 1962, 27, 3320. (c) Kotora, M.; Takahashi, T. In Handbook of Organopalladium Chemistry for Organic Synthesis; Negishi, E., de Meijere, A., Eds.; Wiley-Interscience: New York, 2002; p 973
  51. 39. Gottardo, C.; Kraft, T. M.; Hossain, M. S.; Zawada, P. V.; Muchall, H. M. Can. J. Chem. 2008, 86, 410.
  52. 40. Okuro, K.; Furuune, M.; Enna, M.; Miura, M.; Nomura, M. J. Org. Chem. 1993, 58, 4716.
  53. 41. Li, J. H.; Li, J. L.; Wang, D. P.; Pi, S. F.; Xie, Y. X.; Zhang, M. B.; Hu, X. C. J. Org. Chem. 2007, 72, 2053.
  54. 42. (a) Nicolaou, K. C.; Bulger, P. G.; Sarlah, D. Angew. Chem. Int. Ed. 2005, 44, 4442. (b) Giese, M. W.; Moser, W. H. J. Org. Chem. 2005, 70, 6222. (c) Sumi, S.; Matsumoto, K.; Tokuyama, H.; Fukuyama, T. Org. Lett. 2003, 5, 1891-1893.
  55. 43. (a) Tour, J. M. Acc. Chem. Res. 2000, 33, 791. (b) Martin, R. E.; Diederich, F. Angew. Chem. Int. Ed. 1999, 38, 1350. (c) Tour, J. M. Chem. Rev. 1996, 96, 537. (d) Bunz, U. H. F. Chem. Rev. 2000, 100, 1605. (e) Arnt, L.; Breitenkamp, R. B.; Tew, G. N. Polym. Adv. Technol. 2005, 16, 189. (f) Weder, C. Chem. Commun. 2005, 5378.
  56. Wegner, G., Eds.; Wiley-VCH: Weinheim, 1998; (b) Nalwa, H. S.; Miyata, S. Nonlinear Optics of Organic Molecules and Polymers; CRC Press: Boca Raton, FL, 1997; (c) Supramolecular Photosensitive and Electroactive Materials; Nalwa, H. S., Ed.; Academic Press: San Diego, CA, 2001; (d) Acetylene Chemistry. Chemistry, Biology and Material Science; Diederich, F., Stang, P. J., Tykwinski, R. R. Eds.; Wiley-VCH: Weinheim, 2005.
  57. 45. (a) Sila, B.; Lesiak, T. Roczniki Chemii, 1961, 35, 1519. (b) 陳敏為,甘禮騅 (1990年6月)《有機雜環化合物》(第一版)•北京;高等教育出版社。
  58. 46. Burgstahler, A. W.; Worden, L. R. Organic Syntheses, 1973, 5, 251.
  59. 49. Yue, D.; Yao, T.; Larock, R. C. J. Org. Chem. 2005, 70, 10292.
  60. 50. Swamy, N. K.; Yazici, A.; Pyne, S. G. J. Org. Chem. 2010, 75, 3412.
  61. 51. Jaseer, E. A.; Prasad, D. J. C.; Sekar, G. Tetrahedron 2010, 66, 2077.
  62. 52. Gay, R. M.; Manarin, F.; Schneider, C. C.; Barancelli, D. A.; Costa, M. D.; Zeni, G. J. Org. Chem. 2010, 75, 5701.
  63. 53. (a) Larock, R. C. In Comprehensive Organic Transformations, 2nd ed.; John Wiley & Sons: New York, 1999; pp 1707-1708. (b) Kleemann, A.; Engel, J.; Kutscher, B.; Reichert, D. Pharmaceutical substances syntheses, patents, applications, 4th ed.; Georg Thieme: Stuttgart, 2001. (c) Sundermeier, M.; Zapf, A.; Beller, M. Eur. J. Inorg. Chem. 2003, 3513.
  64. 54. (a) Ellis, G. P.; Romney-Alexander, T. M. Chem. Rev. 1987, 87, 779. (b) Lindley, J. Tetrahedron 1984, 40, 1433. (c) Corbet, J. P.; Mignani, G. Chem. Rev. 2006, 106, 2651.
  65. 55. Beletskaya, I. P.; Sigeev, A. S.; Peregudov, A. S.; Petrovskii, P. V. J. Organomet. Chem. 2004, 689, 3810.
  66. 56. (a) Nowak, I.; Ziolek, M. Chem. Rev. 1999, 99, 3603. (b) Lucke, B.; Narayana, K. V.; Martin, A.; Jahnisch, K. Adv. Synth. Catal. 2004, 346, 1407.
  67. 57. Takagi, K.; Okamoto, T.; Sakakibara, Y.; Oka, S. Chem. Lett. 1973, 2, 471.
  68. 58. (a) Sekiya, A.; Ishikawa, N. Chem. Lett. 1975, 4, 277. (b) Chatani, N.; Hanafusa, T. J. Org. Chem. 1986, 51, 4714.
  69. 59. (a) Percec, V.; Bae, J. Y.; Hill, D. H. J. Org. Chem. 1995, 60, 6895. (b) Grushin, V. V.; Alper, H. Chem. Rev. 1994, 94, 1047. (c) Sasaki, K.; Sakai, M.; Sakakibara, Y.; Takagi, K. Chem. Lett. 1991, 20, 2017.
  70. 60. (a) Erhardt, S.; Grushin, V. V.; Kilpatrick, A. H.; Macgregor, S. A.; Marshall, W. J.; Roe, D. C. J. Am. Chem. Soc. 2008, 130, 4828. (b) Arvela, R. K.; Leadbeater, N. E. J. Org. Chem. 2003, 68, 9122. (c) Sundermeier, M.; Zapf, A.; Beller, M. Eur. J. Inorg. Chem. 2003, 3513. (d) Culkin, D. A.; Hartwig, J. F. Acc. Chem. Res. 2003, 36, 234.
  71. 61. Wang, D.; Kuang, L.; Li, Z.; Ding, K. Synlett 2008, 69.
  72. 65. Hamilton, C. J.; Saravanamuthu, A.; Fairlamb, A. H.; Eggleston, I. M. Bioorg. Med. Chem. 2003, 11, 3683.
  73. 66. Okitsu, T.; Nakazawa, D.; Taniguchi, R.; Wada, A. Org. Lett. 2008, 10, 4967.
  74. 69. Tsai, I. L.; Hsieh, C. F.; Duh, C. Y. Phytochemistry 1998, 48, 1371.
  75. 70. (a) Masseoud, D.; Rott, K.; Liu, B. R.; Agudelo, C. Overview of hyperuricaemia and gout. Curr. Pharm. Des. 2005, 11, 4117. (b) McDonald, M. G.; Rettie, A. E. Chem. Res. Toxicol. 2007, 20, 1833.
  76. 71. (a) Carter, G. A.; Chamberlain, K.; Wain, R. L. Ann. Appl. Biol.
  77. 1978, 88, 57. (b) Zacchino, S.; Rodriguez, G.; Pezzenati, G.; Orellana,
  78. G.; Enriz, R.; Gonzalez, S. M. J. Nat. Prod. 1997, 60, 659. (c) Jiang, X.; Liu, W.; Zhang, W.; Jiang, F.; Gao, Z.; Zhuang, H.; Fu, L. Eur. J. Med. Chem. 2011, 46, 3526.
  79. 72. (a) Masuda, S.; Hasuda, H.; Tokoroyama, T. Chem. Pharm. Bull.
  80. 1994, 42, 2500. (b) Lu, H.; Liu, G. T. Planta Med. 1992, 58, 311. (c)
  81. Silva, D. H. S.; Pereira, F. C.; Zanoni, M. V. B.; Yoshida, M.
  82. J. Nat. Prod. 2000, 63, 1560. (b) Borsato, M. L. C.; Grael, C. F. F.;
  83. 74. (a) 林哲毅論文, 2010, 國立中興大學陳耀鐘老師實驗室 (b)薛清文論文, 2011, 國立中興大學陳耀鐘老師實驗室。
  84. 75. (a) Cho, C. H.; Neuenswander, B.; Lushington, G. H.; Larock, R. C. J. Org. Chem. 2008, 10, 941. (b) Mehta, S.; Larock, R. C. J. Org. Chem. 2010, 75, 1652.
  85. 76. Du, H. A.; Zhang, X. G.; Tang, R. Y.; Li, J. H. J. Org. Chem. 2009, 74, 7844.
  86. 77. 顏千雯論文,2005, 國立中興大學陳耀鐘老師實驗室
  87. 79. Park, K.; Bae, G.; Moon, J.; Choe, J.; Song, K. H.; Lee, S. J. Org. Chem. 2010, 75, 6244.
  88. 80. Ngassa, N.; Lindsey, E. A.; Haines, B. E. Tetrahedron 2009, 65, 4085.
  89. 81. 鍾瑞倫論文, 2011, 國立中興大學陳耀鐘老師實驗室。