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http://dx.doi.org/10.5012/bkcs.2012.33.5.1622

Facile Synthesis of 5-Hydroxy-3-pyrrolin-2-ones from Morita-Baylis-Hillman Adducts  

Lim, Cheol-Hee (Department of Chemistry and Institute of Basic Science, Chonnam National University)
Kim, Sung-Hwan (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)
Publication Information
Bulletin of the Korean Chemical Society / v.33, no.5, 2012 , pp. 1622-1626 More about this Journal
Abstract
An efficient synthetic method of various 5-hydroxy-3-pyrrolin-2-one derivatives has been developed starting from the MBH adducts. In addition, some synthetic applicability of the prepared 5-hydroxy-3-pyrrolin-2-ones was demonstrated including the synthesis of lactam-fused tetrahydroisoquinolines.
Keywords
5-Hydroxy-3-pyrrolin-2-ones; Morita-Baylis-Hillman adducts; Hemiaminals;
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1 Yamashita, M.; Yamashita, T.; Aoyagi, S. Org. Lett. 2011, 13, 2204-2207.   DOI   ScienceOn
2 Wittine, K.; Babic, M. S.; Kosutic, M.; Cetina, M.; Rissanen, K.; Pavelic, S. K.; Paravic, A. T.; Sedic, M.; Pavelic, K.; Mintas, M. Eur. J. Med. Chem. 2011, 46, 2770-2785.   DOI   ScienceOn
3 Li, Y.-H.; Zhou, Y.; Suolang, G.; Bianba, C.; Ding, L.-S.; Feng, H. Helv. Chima. Acta 2011, 94, 474-480.   DOI   ScienceOn
4 Blazecka, P. G.; Belmont, D.; Curran, T.; Pflum, D.; Zhang, J. Org. Lett. 2003, 5, 5015-5017.   DOI   ScienceOn
5 Pattarozzi, M.; Roncaglia, F.; Accorsi, L.; Parsons, A. F.; Ghelfi, F. Tetrahedron 2010, 66, 1357-1364.   DOI   ScienceOn
6 Kumar, N.; Iskander, G. PCT Int. Appl. 2007, WO 2007/085042 (Chem. Abstr. 2007, 147: 235006).
7 Kaluza, Z.; Mostowicz, D.; Dolega, G.; Wojcik, R. Tetrahedron 2008, 64, 2321-2328.   DOI   ScienceOn
8 Kaluza, Z.; Mostowicz, D.; Dolega, G.; Mroczko, K.; Wojcik, R. Tetrahedron 2006, 62, 943-953.   DOI   ScienceOn
9 Zhang, F.; Simpkins, N. S.; Wilson, C. Tetrahedron Lett. 2007, 48, 5942-5947.   DOI   ScienceOn
10 Collado, M. I.; Manteca, I.; Sotomayor, N.; Villa, M.-J.; Lete, E. J. Org. Chem. 1997, 62, 2080-2092.   DOI   ScienceOn
11 Pin, F.; Comesse, S.; Garrigues, B.; Marchalin, S.; Daich, A. J. Org. Chem. 2007, 72, 1181-1191.   DOI   ScienceOn
12 Hitchings, G. J.; Vernon, J. M. J. Chem. Soc., Perkin Trans. 1 1990, 1757-1763.
13 Bahajaj, A. A.; Vernon, J. M.; Wilson, G. D. J. Chem. Soc., Perkin Trans. 1 2001, 1446-1451.
14 Alcaide, B.; Rodriguez-Lopez, J. J. Chem. Soc., Perkin Trans. 1 1990, 2451-2457.
15 Clark, A. J.; Dell, C. P.; McDonagh, J. M.; Geden, J.; Mawdsley, P. Org. Lett. 2003, 5, 2063-2066   DOI   ScienceOn
16 Sortino, M.; Garibotto, F.; Filho, V. C.; Gupta, M.; Enriz, R.; Zacchino, S. Bioorg. Med. Chem. 2011, 19, 2823-2834.   DOI   ScienceOn
17 Ma, S.; Xie, H. J. Org. Chem. 2002, 67, 6575-6578.   DOI   ScienceOn
18 Yang, L.; Lei, C.-H.; Wang, D.-X.; Huang, Z.-T.; Wang, M.-X. Org. Lett. 2010, 12, 3918-3921.   DOI   ScienceOn
19 Basso, A.; Banfi, L.; Galatini, A.; Guanti, G.; Rastrelli, F.; Riva, R. Org. Lett. 2009, 11, 4068-4071.   DOI   ScienceOn
20 Dias-Jurberg, I.; Gagosz, F.; Zard, S. Z. Org. Lett. 2010, 12, 416-419.   DOI   ScienceOn
21 Adib, M.; Mahdavi, M.; Noghani, M. A.; Bijanzadeh, H. R. Tetrahedron Lett. 2007, 48, 8056-8059.   DOI   ScienceOn
22 Adhikari, R.; Jones, D. A.; Liepa, A. J.; Nearn, R. H. Aust. J. Chem. 2005, 58, 882-890.   DOI   ScienceOn
23 Coleman, R. S.; Walczak, M. C.; Campbell, E. L. J. Am. Chem. Soc. 2005, 127, 16038-16039.   DOI   ScienceOn
24 Bouillon, J.-P.; Tinant, B.; Nuzillard, J.-M.; Portella, C. Synthesis 2004, 711-721.
25 Ma, S.; Xie H. Org. Lett. 2000, 2, 3801-3803.   DOI   ScienceOn
26 Jiang, L.-J.; Lan, H.-Q.; Zheng, J.-F.; Ye, J.-L.; Huang, P.-Q. Synlett 2009, 297-301.
27 Kraus, G. A.; Thomas, P. J.; Bougie, D.; Chen, L. J. Org. Chem. 1990, 55, 1624-1627.   DOI
28 Harigaya, Y.; Suzuki, T.; Onda, M. Chem. Pharm. Bull. 1979, 27, 2636-2641.   DOI
29 Broussy, S.; Bernardes- Genisson, V.; Gornitzka, H.; Bernadou, J.; Meunier, B. Org. Biomol. Chem. 2005, 3, 666-669.   DOI   ScienceOn
30 Kim, J. M.; Lee, S.; Kim, S. H.; Lee, H. S.; Kim, J. N. Bull. Korean Chem. Soc. 2008, 29, 2215-2220.   DOI
31 Lim, J. W.; Kim, K. H.; Park, B. R.; Kim, J. N. Tetrahedron Lett. 2011, 52, 6545-6549.   DOI   ScienceOn
32 Yamashita, T.; Yamashita, M.; Aoyagi, S. Tetrahedron Lett. 2011, 52, 4266-4268.   DOI   ScienceOn
33 Kim, K. H.; Lee, H. S.; Kim, S. H.; Lee, K. Y.; Lee, J.-E.; Kim, J. N. Bull. Korean Chem. Soc. 2009, 30, 1012-1020.   DOI
34 Basavaiah, D.; Rao, A. J.; Satyanarayana, T. Chem. Rev. 2003, 103, 811-891.   DOI   ScienceOn
35 Basavaiah, D.; Reddy, B. S.; Badsara, S. S. Chem. Rev. 2010, 110, 5447-5674.   DOI   ScienceOn
36 Kim, J. N.; Lee, K. Y. Curr. Org. Chem. 2002, 6, 627-645.   DOI   ScienceOn
37 Singh, V.; Batra, S. Tetrahedron 2008, 64, 4511-4574.   DOI   ScienceOn
38 Declerck, V.; Martinez, J.; Lamaty, F. Chem. Rev. 2009, 109, 1-48.   DOI   ScienceOn
39 Ciganek, E. In Organic Reactions; Paquette, L. A., Ed.; John Wiley & Sons: New York, 1997; Vol. 51, pp 201-350.
40 Lee, K. Y.; Gowrisankar, S.; Kim, J. N. Bull. Korean Chem. Soc. 2005, 26, 1481-1490.   DOI
41 Radha Krishna, P.; Sachwani, R.; Reddy, P. S. Synlett 2008, 2897-2912.
42 Gowrisankar, S.; Lee, H. S.; Kim, S. H.; Lee, K. Y.; Kim, J. N. Tetrahedron 2009, 65, 8769-8780.   DOI   ScienceOn
43 Snider, B. B.; Neubert, B. J. J. Org. Chem. 2004, 69, 8952-8955   DOI   ScienceOn
44 Agatsuma, T.; Akama, T.; Nara, S.; Matsumiya, S.; Nakai, R.; Ogawa, H.; Otaki, S.; Lkeda, S.-I.; Saitoh, Y.; Kanda, Y. Org. Lett. 2002, 4, 4387-4390.   DOI   ScienceOn
45 Kakeya, H.; Onozawa, C.; Sato, M.; Arai, K.; Osada, H. J. Med. Chem. 1997, 40, 391-394.   DOI   ScienceOn
46 Singh, S. B.; Goetz, M. A.; Jones, E. T.; Bills, G. F.; Giacobbe, R. A.; Herranz, L.; Stevens-Miles, S.; Williams, D. L. J. Org. Chem. 1995, 60, 7040-7042.   DOI