Synthesis of Arene-Fused Isoindoline Derivatives from Morita-Baylis-Hillman Adducts by IMDA Reaction Using Z-Vinylarenes as 1,3-Dienes |
Kim, Ko Hoon
(Department of Chemistry and Institute of Basic Science, Chonnam National University)
Lim, Jin Woo (Department of Chemistry and Institute of Basic Science, Chonnam National University) Moon, Hye Ran (Department of Chemistry and Institute of Basic Science, Chonnam National University) Kim, Jae Nyoung (Department of Chemistry and Institute of Basic Science, Chonnam National University) |
1 | (d) Willmore, N. D.; Hoic, D. A.; Katz, T. J. J. Org. Chem. 1994, 59, 1889-1891. DOI ScienceOn |
2 | (a) Kolis, S. P.; Chordia, M. D.; Liu, R.; Kopach, M. E.; Harman, W. D. J. Am. Chem. Soc. 1998, 120, 2218-2226. DOI ScienceOn |
3 | (b) Stranix, B. R.; Darling, G. D. J. Org. Chem. 1997, 62, 9001-9004. DOI ScienceOn |
4 | (c) Carreno, M. C.; Mahugo, J.; Urbano, A. Tetrahedron Lett. 1997, 38, 3047-3050. DOI ScienceOn |
5 | (a) Drew, M. G. B.; Jahans, A.; Harwood, L. M.; Apoux, S. A. B. H. Eur. J. Org. Chem. 2002, 3589-3594. |
6 | (b) Kotsuki, H.; Kondo, A.; Nishizawa, H.; Ochi, M.; Matsuoka, K. J. Org. Chem. 1981, 46, 5454-5455. DOI |
7 | (c) Marrocchi, A.; Minuti, L.; Taticchi, A.; Scheeren, H. W. Tetrahedron 2001, 57, 4959- 4965. DOI ScienceOn |
8 | (d) Bodalski, R.; Koszuk, J.; Krawczyk, H.; Pietrusiewicz, K. M. J. Org. Chem. 1982, 47, 2219-2220. DOI |
9 | (a) Pedrosa, R.; Andres, C.; Nieto, J. J. Org. Chem. 2002, 67, 782-789. DOI ScienceOn |
10 | (b) Sun, S.; Turchi, I. J.; Xu, D.; Murray, W. V. J. Org. Chem. 2000, 65, 2555-2559. DOI ScienceOn |
11 | (f) Kocsis, L. S.; Benedetti, E.; Brummond, K. M. Org. Lett. 2012, 14, 4430-4433. DOI ScienceOn |
12 | (c) Klemm, L. H.; McGuire, T. M.; Gopinath, K. W. J. Org. Chem. 1976, 41, 2571-2579. DOI |
13 | (d) Dawson, J. R.; Mellor, J. M. Tetrahedron Lett. 1995, 36, 9043-9046. DOI ScienceOn |
14 | (g) Ozawa, T.; Kurahashi, T.; Matsubara, S. Org. Lett. 2011, 13, 5390-5393. DOI ScienceOn |
15 | (h) Park, J.-E.; Lee, J.; Seo, S.-Y.; Shin, D. Tetrahedron Lett. 2014, 55, 818-820. DOI ScienceOn |
16 | (i) Parvatkar, P. T.; Kadam, H. K.; Tilve, S. G. Tetrahedron 2014, 70, 2857-2888 DOI ScienceOn |
17 | (a) Uchida, T.; Rodriquez, M.; Schreiber, S. L. Org. Lett. 2009, 11, 1559-1562. DOI ScienceOn |
18 | (b) Patre, R. E.; Gawas, S.; Sen, S.; Parameswaran, P. S.; Tilve, S. G. Tetrahedron Lett. 2007, 48, 3517-3520. DOI ScienceOn |
19 | (c) Sun, S.; Murray, W. V. J. Org. Chem. 1999, 64, 5941-5945. DOI ScienceOn |
20 | (d) Kotsuki, H.; Kawamura, A.; Ochi, M. Tokoroyama, T. Chem. Lett. 1981, 917-920. |
21 | (e) Cooper, J. A.; Cornwall, P.; Dell, C. P.; Knight, D. W. Tetrahedron Lett. 1988, 29, 2107-2110. DOI ScienceOn |
22 | (f) Kim, P.; Tsuruda, J. M.; Olmstead, M. M.; Eisenberg, S.; Kurth, M. J. Tetrahedron Lett. 2002, 43, 3963-3966. DOI ScienceOn |
23 | (g) Madalengoitia, J. S.; Macdonald, T. L. Tetrahedron Lett. 1993, 34, 6237-6240. DOI ScienceOn |
24 | (h) Torney, P.; Patre, R.; Tilve, S. Synlett 2011, 639-642. |
25 | (a) Hu, Y.; Song, F.; Wu, F.; Cheng, D.; Wang, S. Chem. Eur. J. 2008, 14, 3110-3117. DOI ScienceOn |
26 | (i) He, Y.; Krishnamoorthy, P.; Lima, H. M.; Chen, Y.; Wu, H.; Sivappa, R.; Dias, H. V. R.; Lovely, C. J. Org. Biomol. Chem. 2011, 9, 2685-2701. DOI ScienceOn |
27 | (j) He, Y.; Chen, Y.; Wu, H.; Lovely, C. J. Org. Lett. 2003, 5, 3623-3626. |
28 | (d) Ohno, H.; Miyamura, K.; Mizutani, T.; Kadoh, Y.; Takeoka, Y.; Hamaguchi, H.; Tanaka, T. Chem. Eur. J. 2005, 11, 3728-3741. DOI ScienceOn |
29 | (b) Hu, Y.; Ouyang, Y.; Qu, Y.; Hu, Q.; Yao, H. Chem. Commun. 2009, 4575-4577. |
30 | (c) Hu, Y.; Qu, Y.; Wu, F.; Gui, J.; Wei, Y.; Hu, Q.; Wang, S. Chem. Asian J. 2010, 5, 309-314. DOI ScienceOn |
31 | (e) Ohno, H.; Miyamura, K.; Takeoka, Y.; Tanaka, T. Angew. Chem. Int. Ed. 2003, 42, 2647-2650. DOI ScienceOn |
32 | (a) Basavaiah, D.; Rao, A. J.; Satyanarayana, T. Chem. Rev. 2003, 103, 811-891. DOI ScienceOn |
33 | (b) Basavaiah, D.; Reddy, B. S.; Badsara, S. S. Chem. Rev. 2010, 110, 5447-5674. DOI ScienceOn |
34 | (c) Singh, V.; Batra, S. Tetrahedron 2008, 64, 4511-4574. DOI ScienceOn |
35 | (d) Declerck, V.; Martinez, J.; Lamaty, F. Chem. Rev. 2009, 109, 1-48. DOI ScienceOn |
36 | (e) Ciganek, E. In Organic Reactions; Paquette, L. A., Ed.; John Wiley & Sons: New York, 1997; Vol. 51, pp 201-350. |
37 | (f) Kim, J. N.; Lee, K. Y. Curr. Org. Chem. 2002, 6, 627-645. |
38 | Howell, B. A.; Powers, J. J.; Priddy, D. B. Polym. Prepr. 2002, 43, 386-387. |
39 | (g) Lee, K. Y.; Gowrisankar, S.; Kim, J. N. Bull. Korean Chem. Soc. 2005, 26, 1481-1490. |
40 | (h) Gowrisankar, S.; Lee, H. S.; Kim, S. H.; Lee, K. Y.; Kim, J. N. Tetrahedron 2009, 65, 8769-8780. DOI ScienceOn |
41 | (b) Nieto-Garcia, O.; Alonso, R. J. Org. Chem. 2013, 78, 2564-2570. |
42 | (i) Shi, M.; Wang, F.-J.; Zhao, M.-X.; Wei, Y. The Chemistry of the Morita-Baylis-Hillman Reaction; RSC Publishing: Cambridge, UK, 2011. |
43 | (b) Fishwick, C. W. G.; Grigg, R.; Sridharan, V.; Virica, J. Tetrahedron 2003, 59, 4451-4468. DOI ScienceOn |
44 | Kappe, C. O.; Murphree, S. S.; Padwa, A. Tetrahedron 1997, 53, 14179-14233 and further references cited therein. DOI ScienceOn |
45 | (c) Chen, Y.; Wang, L.; Liu, Y.; Li, Y. Chem. Eur. J. 2011, 17, 12582-12586. |
46 | (d) Liu, L.; Gao, Y.; Che, C.; Wu, N.; Wang, D. Z.; Li, C.-C.; Yang, Z. Chem. Commun. 2009, 662-664. (e) Li, C.-C.; Liang, S.; Zhang, X.-H.; Xie, Z.-X.; Chen, J.-H.; Wu, Y.-D.; Yang, Z. Org. Lett. 2005, 7, 3709-3712. |
47 | Anderson, M. R.; Brown, R. F. C.; Coulston, K. J.; Eastwood, F. W.; Ward, A. Aus. J. Chem. 1990, 43, 1137-1150. |
48 | (b) Doecke, C. W.; Garratt, P. J. J. Chem. Soc., Chem. Commun. 1981, 873-874. |
49 | (c) Rodriguez, D.; Navarro-Vazquez, A. Castedo, L.; Dominguez, D.; Saa, C. J. Am. Chem. Soc. 2001, 123, 9178-9179. |
50 | (c) Thummel, R. P. J. Chem. Soc., Chem. Commun. 1974, 899-900. |
51 | (a) Hu, Y.-M.; Lim, X.-G.; Zhu, T.; Wan, J.; Sun, Y.-J.; Zhao, Q.-S.; Yu, T. Synthesis 2010, 3467-3473. |
52 | (b) Shibata, T.; Fujiwara, R.; Takano, D. Synlett 2005, 2062-2066. |
53 | (a) Matsumoto, K.; Goto, S.; Hayashi, N.; Iida, H.; Uchida, T.; Kakehi, A. Eur. J. Org. Chem. 2004, 4667-4671. |
54 | (k) Hayakawa, K.; Nagatsugi, F.; Kanematsu, K. J. Org. Chem. 1988, 53, 860-863. DOI |
55 | (e) Chackalamannil, S.; Doller, D.; Clasby, M.; Xia, Y.; Eagen, K.; Lin, Y.; Tsai, H.-A.; McPhail, A. T. Tetrahedron Lett. 2000, 41, 4043-4047. DOI ScienceOn |
56 | Kim, K. H.; Lee, S.; Lee, J.; Go, M. J.; Kim, J. N. Tetrahedron Lett. 2013, 54, 5739-5743 DOI ScienceOn |
57 | (a) Ding, M.; He, F.; Hudyma, T. W.; Zheng, X.; Poss, M. A.; Kadow, J. F.; Beno, B. R.; Rigat, K. L.; Wang, Y.-K.; Fridell, R. A.; Lemm, J. A.; Qiu, D.; Liu, M.; Voss, S.; Pelosi, L. A.; Roberts, S. B.; Gao, M.; Knipe, J.; Gentles, R. G. Bioorg. Med. Chem. Lett. 2012, 22, 2866-2871. |