DOI QR코드

DOI QR Code

Morita-Baylis-Hillman Route to Dimethyl 2,3-Dihydrobenzo[b]oxepine-2,4-dicarboxylates and Methyl 2-(2-Carbomethoxybenzo[b]furan-3-yl)propanoates from Salicylaldehydes

  • Ahn, Sang-Hyun (Department of Chemical Engineering, Hanyang University) ;
  • Jang, Seung-Soon (Department of Chemical Engineering, Hanyang University) ;
  • Kim, Young-Keun (Department of Chemical Engineering, Hanyang University) ;
  • Lee, Kee-Jung (Department of Chemical Engineering, Hanyang University)
  • Received : 2011.11.17
  • Accepted : 2011.11.21
  • Published : 2012.01.20

Abstract

A new synthetic method for dimethyl 2,3-dihydrobenzo[b]oxepine-2,4-dicarboxylates and methyl 2-(2-carbomethoxybenzo[b]furan-3-yl)propanoates by an intramolecular conjugate displacement reaction or an $S_N2$ reaction of acetates of Morita-Baylis-Hillman adducts of methyl (2-formylphenoxy)acetates has been described.

Keywords

References

  1. Hoberg, J. O. Tetrahedron 1998, 54, 12631. https://doi.org/10.1016/S0040-4020(98)00596-1
  2. Snyder, N. L.; Haines, H. M.; Peczuh, M. W. Tetrahedron 2006, 62, 9301. https://doi.org/10.1016/j.tet.2006.07.021
  3. Basavaiah, D.; Sharada, D. S.; Veerendhar, A. Tetrahedron Lett. 2004, 45, 3081. https://doi.org/10.1016/j.tetlet.2004.02.107
  4. Das, B.; Majhi, A.; Banerjee, J.; Chowdhury, N.; Holla, H.; Harakishore, K.; Murty, U. S. Chem. Pharm. Bull. 2006, 54, 403. https://doi.org/10.1248/cpb.54.403
  5. Macias, F. A.; Varela, R. M.; Torres, A.; Molinillo, J. M. G. Tetrahedron Lett. 1999, 40, 4725. https://doi.org/10.1016/S0040-4039(99)00833-3
  6. Wijnberg, J. B. P. A.; van Veldhuizen, A.; Swarts, H. J.; Frankland, J. C.; Field, J. A. Tetrahedron Lett. 1999, 40, 5767. https://doi.org/10.1016/S0040-4039(99)01074-6
  7. Asakawa, Y.; Hashimoto, T.; Takikawa, K.; Tori, M.; Ogawa, S. Phytochemistry 1991, 30, 235. https://doi.org/10.1016/0031-9422(91)84130-K
  8. Asakawa, Y.; Takeda, R.; Toyota, M.; Takemoto, T. Phytochemistry 1981, 20, 858. https://doi.org/10.1016/0031-9422(81)85201-6
  9. Baba, M.; Nishimura, O.; Kanzaki, N.; Okamoto, M.; Sawada, H.; Iizawa, Y.; Shiraishi, M.; Aramaki, Y.; Okonogi, K.; Ogawa, Y.; Meguro, K.; Fujino, M. Proc. Natl. Acad. Sci. U. S. A. 1999, 96, 5698. https://doi.org/10.1073/pnas.96.10.5698
  10. Shiraishi, M.; Aramaki, Y.; Seto, M.; Imoto, H.; Nishikawa, Y.; Kanzaki, N.; Okamoto, M.; Sawada, H.; Nishimura, O.; Baba, M.; Fujino, M. J. Med. Chem. 2000, 43, 2049. https://doi.org/10.1021/jm9906264
  11. Imamura, S.; Ishihara, Y.; Hattori, T.; Kurasawa, O.; Matsushita, Y.; Sugihara, Y.; Kanzaki, N.; Iizawa, Y.; Baba, M.; Hashiguchi, S. Chem. Pharm. Bull. 2004, 52, 63. https://doi.org/10.1248/cpb.52.63
  12. Aramaki, Y.; Seto, M.; Okawa, T.; Oda, T.; Kanzaki, N.; Shiraishi, M. Chem. Pharm. Bull. 2004, 52, 254. https://doi.org/10.1248/cpb.52.254
  13. Seto, M.; Aramaki, Y.; Imoto, H.; Aikawa, K.; Oda, T.; Kanzaki, N.; Iizawa, Y.; Baba, M.; Shiraishi, M. Chem. Pharm. Bull. 2004, 52, 818. https://doi.org/10.1248/cpb.52.818
  14. Seto, M.; Aramaki, Y.; Okawa, T.; Miyamoto, N.; Aikawa, K.; Kanzaki, N.; Niwa, S.; Iizawa, Y.; Baba, M.; Shiraishi, M. Chem. Pharm. Bull. 2004, 52, 577. https://doi.org/10.1248/cpb.52.577
  15. Seto, M.; Miyamoto, N.; Aikawa, K.; Aramaki, Y.; Kanzaki, N.; Iizawa, Y.; Baba, M.; Shiraishi, M. Bioorg. Med. Chem. 2005, 13, 363. https://doi.org/10.1016/j.bmc.2004.10.021
  16. Sabui, S. K.; Venkateswaran, R. V. Tetrahedron Lett. 2004, 45, 2047. https://doi.org/10.1016/j.tetlet.2004.01.085
  17. Fujiwara, T.; Koto, Y.; Takeda, T. Tetrahedron 2000, 56, 4859. https://doi.org/10.1016/S0040-4020(00)00201-5
  18. Fuchs, P. L. J. Am. Chem. Soc. 1974, 96, 1607. https://doi.org/10.1021/ja00812a062
  19. Kahnberg, P.; Lee, C. W.; Grubbs, R. H.; Sterner, O. Tetrahedron 2002, 58, 5203. https://doi.org/10.1016/S0040-4020(02)00505-7
  20. Nishiguchi, A.; Ikemoto, T.; Ito, T.; Miura, S.; Tomimatsu, K. Heterocycles 2007, 71, 445. https://doi.org/10.3987/COM-06-10941
  21. Liu, G.; Lu, X. Adv. Synth. Catal. 2007, 349, 2247. https://doi.org/10.1002/adsc.200700369
  22. Li, Y.; Jardine, K. J.; Tan, R.; Song, D.; Dong, V. M. Angew. Chem. Int. Ed. 2009, 48, 9690. https://doi.org/10.1002/anie.200905478
  23. Aboraia, A. S.; Yee, S. W.; Gomaa, M. S.; Shah, N.; Robotham, A. C.; Makowski, B.; Prosser, D.; Brancale, A.; Jones, G.; Simons, C. Bioorg. Med. Chem. 2010, 18, 4939. https://doi.org/10.1016/j.bmc.2010.06.011
  24. Negoro, N.; Sasaki, S.; Mikami, S.; Ito, M.; Suzuki, M.; Tsujihata, Y.; Ito, R.; Harada, A.; Takeuchi, K.; Suzuki, N.; Miyazaki, J.; Santou, T.; Odani, T.; Kanzaki, N.; Funami, M.; Tanaka, T.; Kogame, A.; Matsunaga, S.; Yasuma, T.; Momose, Y. ACS Med. Chem. Lett. 2010, 1, 290. https://doi.org/10.1021/ml1000855
  25. Li, J.; Rush, T. S., III.; Li, W.; DeVincentis, D.; Du, X.; Hu, Y.; Thomason, J. R.; Xiang, J. S.; Skotnicki, J. S.; Tam, S.; Cunningham, K. M.; Chockalingam, P. S.; Morris, E. A.; Levin, J. I. Bioorg. Med. Chem. Lett. 2005, 15, 4961. https://doi.org/10.1016/j.bmcl.2005.08.001
  26. Davis, M. C.; Groshens, T. J.; Parrish, D. A. Synth. Commun. 2010, 40, 3008. https://doi.org/10.1080/00397910903351568
  27. Suzuki, T.; Horaguchi, T.; Shimizu, T.; Abe, T. Bull. Chem. Soc. Jpn. 1993, 56, 2762
  28. Teague, S. J.; Barber, S. Tetrahedron Lett. 2010, 51, 4720. https://doi.org/10.1016/j.tetlet.2010.07.020
  29. Fall, Y.; Santana, L.; Teijeira, M.; Uriarte, E. Heterocycles 1995, 41, 647. https://doi.org/10.3987/COM-94-6996
  30. Drews, S. E.; Roos, G. H. P. Tetrahedron 1988, 44, 4653. https://doi.org/10.1016/S0040-4020(01)86168-8
  31. Basavaiah, D.; Rao, P. D.; Hyma, R. S. Tetrahedron 1996, 52, 8001. https://doi.org/10.1016/0040-4020(96)00154-8
  32. Ciganek, E. Org. React. 1997, 51, 201.
  33. Langer, P. Angew. Chem. Int. Ed. 2000, 39, 3049. https://doi.org/10.1002/1521-3773(20000901)39:17<3049::AID-ANIE3049>3.0.CO;2-5
  34. Kim, J. N.; Lee, K. Y. Curr. Org. Chem. 2002, 6, 627. https://doi.org/10.2174/1385272023374094
  35. Basavaiah, D.; Rao, A. J.; Satyanarayana, T. Chem. Rev. 2003, 103, 811. https://doi.org/10.1021/cr010043d
  36. Kataoka, T.; Kinoshita, H. Eur. J. Org. Chem. 2005, 45.
  37. Lee, K. Y.; Gowrisankar, S.; Kim, J. N. Bull. Korean Chem. Soc. 2005, 26, 1481. https://doi.org/10.5012/bkcs.2005.26.10.1481
  38. Basavaiah, D.; Rao, K. V.; Reddy, R. J. Chem. Soc. Rev. 2007, 36, 1581. https://doi.org/10.1039/b613741p
  39. Singh, V.; Batra, S. Tetrahedron 2008, 64, 4511. https://doi.org/10.1016/j.tet.2008.02.087
  40. Declerck, V.; Martinez, J.; Lamaty, F. Chem. Rev. 2009, 109, 1. https://doi.org/10.1021/cr068057c
  41. Ma, G.-N.; Jiang, J.-J.; Shi, M.; Wei, Y. Chem. Commun. 2009, 5496.
  42. Basavaiah, D.; Reddy, B. S.; Badsara, S. S. Chem. Rev. 2010, 110, 5447. https://doi.org/10.1021/cr900291g
  43. Zhong, W.; Liu, Y.; Wang, G.; Hong, L.; Chen, Y.; Chen, X.; Zheng, Y.; Zhang, W.; Ma, W.; Shen, Y.; Yao, Y. Org. Prep. Proced. Int. 2011, 43, 1. https://doi.org/10.1080/00304948.2011.549065
  44. Kaye, P. T.; Musa, M. A.; Nocanda, X. W. Synthesis 2003, 531.
  45. Kaye, P. T.; Musa, M. A. Synth. Commun. 2003, 33, 1755. https://doi.org/10.1081/SCC-120018937
  46. Lee, K. Y.; Kim, J. M.; Kim, J. N. Bull. Korean Chem. Soc. 2003, 24, 17. https://doi.org/10.5012/bkcs.2003.24.1.017
  47. Lesch, B.; Brase, S. Angew. Chem. Int. Ed. 2004, 43, 115. https://doi.org/10.1002/anie.200352154
  48. Ahn, S.-H.; Lim, H. N.; Lee, K.-J. J. Heterocycl. Chem. 2008, 45, 1701. https://doi.org/10.1002/jhet.5570450622
  49. Hong, W. P.; Lim, H. N.; Park, H. W.; Lee, K.-J. Bull. Korean Chem. Soc. 2005, 26, 655. https://doi.org/10.5012/bkcs.2005.26.4.655
  50. Hong, W. P.; Lee, K.-J. Synthesis 2005, 33.
  51. Hong, W. P.; Lee, K.-J. Synthesis 2006, 963.
  52. Song, Y. S.; Lee, K.-J. J. Heterocycl. Chem. 2006, 43, 1721. https://doi.org/10.1002/jhet.5570430647
  53. Ji, S.-H.; Hong, W. P.; Ko, S. H.; Lee, K.-J. J. Heterocycl. Chem. 2006, 43, 799. https://doi.org/10.1002/jhet.5570430344
  54. Lim, H. N.; Ji, S.-H.; Lee, K.-J. Synthesis 2007, 2454.
  55. Song, Y. S.; Lee, K.-J. Synthesis 2007, 3037.
  56. Lim, H. N.; Song, Y. S.; Lee, K.-J. Synthesis 2007, 3376.
  57. Jeon, K. J.; Lee, K.-J. J. Heterocycl. Chem. 2008, 45, 615. https://doi.org/10.1002/jhet.5570450252
  58. Park, S. P.; Song, Y. S.; Lee, K.-J. Tetrahedron 2009, 65, 4703. https://doi.org/10.1016/j.tet.2009.04.026
  59. Han, E.-G.; Kim, H. J.; Lee, K.-J. Tetrahedron 2009, 65, 9616. https://doi.org/10.1016/j.tet.2009.09.047
  60. Park, S. P.; Ahn, S.-H.; Lee, K.-J. Tetrahedron 2010, 66, 3490. https://doi.org/10.1016/j.tet.2010.03.017
  61. Ahn, S.-H.; Jang, S. S.; Han, E.- G.; Lee, K.-J. Synthesis 2011, 377.
  62. Clive, D. L. J.; Li, Z.; Yu, M. J. Org. Chem. 2007, 72, 5608. https://doi.org/10.1021/jo070664s
  63. Prabhudas, B.; Clive, D. L. J. Angew. Chem. Int. Ed. 2007, 46, 9295. https://doi.org/10.1002/anie.200703022
  64. Wang, L.; Prabhudas, B.; Clive, D. L. J. J. Am. Chem. Soc. 2009, 131, 6003. https://doi.org/10.1021/ja900857h
  65. Buckle, D. R.; Fenwick, A. E.; Outred, D. J.; Rockell, C. J. M. J. Chem. Research (S) 1987, 394.
  66. Desai, N. C.; Dave, D.; Shah, M. D.; Vyas, G. D. Indian J. Chem. Sect. B: Org. Chem. Incl. Med. Chem. 2000, 39B, 277; Chem. Abstr. 134, 100808.
  67. Desai, N. C.; Dave, D.; Shah, M. D.; Vyas, G. D. Chem. Abstr. 134, 100808.
  68. Lee, K. Y.; Kim, J. M.; Kim, J. N. Synlett 2003, 357.
  69. Mason, P. H.; Emslie, N. D. Tetrahedron 1994, 50, 12001. https://doi.org/10.1016/S0040-4020(01)89311-X
  70. Das, B.; Venkateswarlu, K.; Krishnaiah, M.; Holla, H.; Majhi, A. Helv. Chim. Acta 2006, 89, 1417. https://doi.org/10.1002/hlca.200690141
  71. Sa, M. M.; Fernandes, L.; Ferreira, M.; Bortoluzzi, A. J. Tetrahedron Lett. 2008, 49, 1228. https://doi.org/10.1016/j.tetlet.2007.12.029
  72. Karpenko, A. S.; Dorovskykh, I. V.; Shibinskaya, M. O.; Maltsev, G. V.; Lyakhova, H. A.; Gusyeva, Ju. O.; Zholobak, N. M.; Spivak, N. Ya.; Lyakhov, S. A.; Andronati, S. A. Ukrainica Bioorganica Acta 2008, 6, 65
  73. Karpenko, A. S.; Dorovskykh, I. V.; Shibinskaya, M. O.; Maltsev, G. V.; Lyakhova, H. A.; Gusyeva, Ju. O.; Zholobak, N. M.; Spivak, N. Ya.; Lyakhov, S. A.; Andronati, S. A. Chem. Abstr. 151, 550047.
  74. Qian, W.; Bao, W.; Zhang, Y. Synlett 1997, 393.
  75. Movassagh, B.; Shamsipoor, M. Synlett 2005, 121.
  76. Hsiao, C.-N.; Bhagavatula, L.; Pariza, R. J. Synth. Commun. 1990, 20, 1678.
  77. Beck, J. R. J. Org. Chem. 1972, 37, 3224. https://doi.org/10.1021/jo00986a007
  78. Carreras, I.; Scherkenbeck, J.; Paulitz, C. Comb. Chem. High T. Scr. 2005, 8, 643.
  79. Baettig, U.; Cox, B.; Janus, D.; Leblanc, C.; Sandham, D. A.; Turner, K. L.; Watson, S. J. PCT Int. Appl. WO 2006125593, 2006
  80. Baettig, U.; Cox, B.; Janus, D.; Leblanc, C.; Sandham, D. A.; Turner, K. L.; Watson, S. J. Chem. Abstr. 2006, 146, 7693.

Cited by

  1. Ru(II)-Catalyzed C-H Activation/Alkylation of 3-Formylbenzofurans with Conjugated Olefins: Product Divergence vol.84, pp.9, 2012, https://doi.org/10.1021/acs.joc.8b03267