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http://dx.doi.org/10.5012/bkcs.2012.33.1.233

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)
Publication Information
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
Morita-Baylis-Hillman; $S_N2-S_N2 Reaction; 2,3-Dihydrobenzo[b]oxepines; Benzo[b]furans; Methyl (2-formylphenoxy)acetates;
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1 Clive, D. L. J.; Li, Z.; Yu, M. J. Org. Chem. 2007, 72, 5608.   DOI   ScienceOn
2 Prabhudas, B.; Clive, D. L. J. Angew. Chem. Int. Ed. 2007, 46, 9295.   DOI   ScienceOn
3 Wang, L.; Prabhudas, B.; Clive, D. L. J. J. Am. Chem. Soc. 2009, 131, 6003.   DOI   ScienceOn
4 Buckle, D. R.; Fenwick, A. E.; Outred, D. J.; Rockell, C. J. M. J. Chem. Research (S) 1987, 394.
5 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.
6 Lee, K. Y.; Kim, J. M.; Kim, J. N. Synlett 2003, 357.
7 Mason, P. H.; Emslie, N. D. Tetrahedron 1994, 50, 12001.   DOI   ScienceOn
8 Das, B.; Venkateswarlu, K.; Krishnaiah, M.; Holla, H.; Majhi, A. Helv. Chim. Acta 2006, 89, 1417.   DOI   ScienceOn
9 Sa, M. M.; Fernandes, L.; Ferreira, M.; Bortoluzzi, A. J. Tetrahedron Lett. 2008, 49, 1228.   DOI   ScienceOn
10 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
11 Qian, W.; Bao, W.; Zhang, Y. Synlett 1997, 393.
12 Movassagh, B.; Shamsipoor, M. Synlett 2005, 121.
13 Hsiao, C.-N.; Bhagavatula, L.; Pariza, R. J. Synth. Commun. 1990, 20, 1678.
14 Beck, J. R. J. Org. Chem. 1972, 37, 3224.   DOI
15 Carreras, I.; Scherkenbeck, J.; Paulitz, C. Comb. Chem. High T. Scr. 2005, 8, 643.
16 Baettig, U.; Cox, B.; Janus, D.; Leblanc, C.; Sandham, D. A.; Turner, K. L.; Watson, S. J. PCT Int. Appl. WO 2006125593, 2006
17 Basavaiah, D.; Reddy, B. S.; Badsara, S. S. Chem. Rev. 2010, 110, 5447.   DOI   ScienceOn
18 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.   DOI   ScienceOn
19 Kaye, P. T.; Musa, M. A.; Nocanda, X. W. Synthesis 2003, 531.
20 Kaye, P. T.; Musa, M. A. Synth. Commun. 2003, 33, 1755.   DOI   ScienceOn
21 Lee, K. Y.; Kim, J. M.; Kim, J. N. Bull. Korean Chem. Soc. 2003, 24, 17.   DOI   ScienceOn
22 Lesch, B.; Brase, S. Angew. Chem. Int. Ed. 2004, 43, 115.   DOI   ScienceOn
23 Ahn, S.-H.; Lim, H. N.; Lee, K.-J. J. Heterocycl. Chem. 2008, 45, 1701.   DOI   ScienceOn
24 Hong, W. P.; Lim, H. N.; Park, H. W.; Lee, K.-J. Bull. Korean Chem. Soc. 2005, 26, 655.   DOI   ScienceOn
25 Hong, W. P.; Lee, K.-J. Synthesis 2005, 33.
26 Hong, W. P.; Lee, K.-J. Synthesis 2006, 963.
27 Song, Y. S.; Lee, K.-J. J. Heterocycl. Chem. 2006, 43, 1721.   DOI   ScienceOn
28 Ji, S.-H.; Hong, W. P.; Ko, S. H.; Lee, K.-J. J. Heterocycl. Chem. 2006, 43, 799.   DOI   ScienceOn
29 Lim, H. N.; Ji, S.-H.; Lee, K.-J. Synthesis 2007, 2454.
30 Song, Y. S.; Lee, K.-J. Synthesis 2007, 3037.
31 Lim, H. N.; Song, Y. S.; Lee, K.-J. Synthesis 2007, 3376.
32 Jeon, K. J.; Lee, K.-J. J. Heterocycl. Chem. 2008, 45, 615.   DOI   ScienceOn
33 Park, S. P.; Song, Y. S.; Lee, K.-J. Tetrahedron 2009, 65, 4703.   DOI   ScienceOn
34 Han, E.-G.; Kim, H. J.; Lee, K.-J. Tetrahedron 2009, 65, 9616.   DOI   ScienceOn
35 Park, S. P.; Ahn, S.-H.; Lee, K.-J. Tetrahedron 2010, 66, 3490.   DOI   ScienceOn
36 Ahn, S.-H.; Jang, S. S.; Han, E.- G.; Lee, K.-J. Synthesis 2011, 377.
37 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.   DOI   ScienceOn
38 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.   DOI   ScienceOn
39 Davis, M. C.; Groshens, T. J.; Parrish, D. A. Synth. Commun. 2010, 40, 3008.   DOI   ScienceOn
40 Suzuki, T.; Horaguchi, T.; Shimizu, T.; Abe, T. Bull. Chem. Soc. Jpn. 1993, 56, 2762
41 Teague, S. J.; Barber, S. Tetrahedron Lett. 2010, 51, 4720.   DOI   ScienceOn
42 Fall, Y.; Santana, L.; Teijeira, M.; Uriarte, E. Heterocycles 1995, 41, 647.   DOI   ScienceOn
43 Drews, S. E.; Roos, G. H. P. Tetrahedron 1988, 44, 4653.   DOI   ScienceOn
44 Basavaiah, D.; Rao, P. D.; Hyma, R. S. Tetrahedron 1996, 52, 8001.   DOI   ScienceOn
45 Ciganek, E. Org. React. 1997, 51, 201.
46 Kataoka, T.; Kinoshita, H. Eur. J. Org. Chem. 2005, 45.
47 Langer, P. Angew. Chem. Int. Ed. 2000, 39, 3049.   DOI   ScienceOn
48 Kim, J. N.; Lee, K. Y. Curr. Org. Chem. 2002, 6, 627.   DOI   ScienceOn
49 Basavaiah, D.; Rao, A. J.; Satyanarayana, T. Chem. Rev. 2003, 103, 811.   DOI   ScienceOn
50 Lee, K. Y.; Gowrisankar, S.; Kim, J. N. Bull. Korean Chem. Soc. 2005, 26, 1481.   DOI   ScienceOn
51 Basavaiah, D.; Rao, K. V.; Reddy, R. J. Chem. Soc. Rev. 2007, 36, 1581.   DOI   ScienceOn
52 Singh, V.; Batra, S. Tetrahedron 2008, 64, 4511.   DOI   ScienceOn
53 Declerck, V.; Martinez, J.; Lamaty, F. Chem. Rev. 2009, 109, 1.   DOI   ScienceOn
54 Ma, G.-N.; Jiang, J.-J.; Shi, M.; Wei, Y. Chem. Commun. 2009, 5496.
55 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.   DOI   ScienceOn
56 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.   DOI   ScienceOn
57 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.   DOI   ScienceOn
58 Aramaki, Y.; Seto, M.; Okawa, T.; Oda, T.; Kanzaki, N.; Shiraishi, M. Chem. Pharm. Bull. 2004, 52, 254.   DOI   ScienceOn
59 Seto, M.; Aramaki, Y.; Imoto, H.; Aikawa, K.; Oda, T.; Kanzaki, N.; Iizawa, Y.; Baba, M.; Shiraishi, M. Chem. Pharm. Bull. 2004, 52, 818.   DOI   ScienceOn
60 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.   DOI   ScienceOn
61 Seto, M.; Miyamoto, N.; Aikawa, K.; Aramaki, Y.; Kanzaki, N.; Iizawa, Y.; Baba, M.; Shiraishi, M. Bioorg. Med. Chem. 2005, 13, 363.   DOI   ScienceOn
62 Sabui, S. K.; Venkateswaran, R. V. Tetrahedron Lett. 2004, 45, 2047.   DOI   ScienceOn
63 Fujiwara, T.; Koto, Y.; Takeda, T. Tetrahedron 2000, 56, 4859.   DOI   ScienceOn
64 Fuchs, P. L. J. Am. Chem. Soc. 1974, 96, 1607.   DOI
65 Kahnberg, P.; Lee, C. W.; Grubbs, R. H.; Sterner, O. Tetrahedron 2002, 58, 5203.   DOI   ScienceOn
66 Nishiguchi, A.; Ikemoto, T.; Ito, T.; Miura, S.; Tomimatsu, K. Heterocycles 2007, 71, 445.   DOI   ScienceOn
67 Liu, G.; Lu, X. Adv. Synth. Catal. 2007, 349, 2247.   DOI   ScienceOn
68 Li, Y.; Jardine, K. J.; Tan, R.; Song, D.; Dong, V. M. Angew. Chem. Int. Ed. 2009, 48, 9690.   DOI   ScienceOn
69 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.   DOI   ScienceOn
70 Desai, N. C.; Dave, D.; Shah, M. D.; Vyas, G. D. Chem. Abstr. 134, 100808.
71 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.
72 Baettig, U.; Cox, B.; Janus, D.; Leblanc, C.; Sandham, D. A.; Turner, K. L.; Watson, S. J. Chem. Abstr. 2006, 146, 7693.
73 Hoberg, J. O. Tetrahedron 1998, 54, 12631.   DOI   ScienceOn
74 Snyder, N. L.; Haines, H. M.; Peczuh, M. W. Tetrahedron 2006, 62, 9301.   DOI   ScienceOn
75 Basavaiah, D.; Sharada, D. S.; Veerendhar, A. Tetrahedron Lett. 2004, 45, 3081.   DOI   ScienceOn
76 Das, B.; Majhi, A.; Banerjee, J.; Chowdhury, N.; Holla, H.; Harakishore, K.; Murty, U. S. Chem. Pharm. Bull. 2006, 54, 403.   DOI   ScienceOn
77 Macias, F. A.; Varela, R. M.; Torres, A.; Molinillo, J. M. G. Tetrahedron Lett. 1999, 40, 4725.   DOI   ScienceOn
78 Wijnberg, J. B. P. A.; van Veldhuizen, A.; Swarts, H. J.; Frankland, J. C.; Field, J. A. Tetrahedron Lett. 1999, 40, 5767.   DOI   ScienceOn
79 Asakawa, Y.; Hashimoto, T.; Takikawa, K.; Tori, M.; Ogawa, S. Phytochemistry 1991, 30, 235.   DOI   ScienceOn
80 Asakawa, Y.; Takeda, R.; Toyota, M.; Takemoto, T. Phytochemistry 1981, 20, 858.   DOI   ScienceOn