Bulletin of the Korean Chemical Society

Korean Chemical Society (대한화학회)
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Solvent-Free Michael Addition Between EMME and Secondary Amine under Focused Microwave Irradiation

  • Kim, Ki-Won (Department of Chemistry, Kyungsung University) ;
  • Lee, Hee-Jung (Department of Chemical Education, Kyungsung University) ;
  • Jo, Jeong-Im (Department of Chemistry, Kyungsung University) ;
  • Kwon, Tae-Woo (Department of Chemistry, Kyungsung University)
  • Received : 2009.11.06
  • Accepted : 2010.02.24
  • Published : 2010.05.20
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Abstract

Microwave-assisted Michael reaction between EMME and various amines such as diphenylamine, 4-methyl-N-phenylbenzenamine, N-phenylnaphthalen-1-amine, dihexylamine, diisopropylamine, and 4-nitrobenzenamine were described. Solvent-free conditions on alumina as solid support in the presence of $K_2CO_3$ catalysts gave moderate to good yields (55 - 93%) of diethylmalonate analogues having enamine moieties under focused microwave irradiation.

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References

  1. Lesher, G. Y.; Froelich, E. J.; Gruett, M. D.; Bailey, J. H.; Brundage, R. P. J. Med. Pharm. Chem. 1962, 91, 1063.
  2. Mitscher, Lester A. Chem. Rev. 2005, 105, 559. https://doi.org/10.1021/cr030101q
  3. Koga, H.; Ito, A.; Murayama, S.; Suzue, S.; Irikura, T. J. Med. Chem. 1980, 23(12), 1358. https://doi.org/10.1021/jm00186a014
  4. Hayakawa, I.; Hiramitsu, T.; Tanaka, Y. Chem. Pharm. Bull. 1984, 32, 4907. https://doi.org/10.1248/cpb.32.4907
  5. Atarashi, S.; Yokahama, S.; Yamazaki, K.; Sakano, K.; Imamura, M.; Hayakawa, I. Chem. Pharm. Bull. 1987, 35, 1896. https://doi.org/10.1248/cpb.35.1896
  6. Santilli, A. A.; Bruce, W. F.; Osdene, T. S. J. Med. Chem. 1963, 7(1), 68. https://doi.org/10.1021/jm00331a015
  7. Steck, E. A. J. Org. Chem. 1962, 27, 306. https://doi.org/10.1021/jo01048a517
  8. Banerji, B.; Conejo-Garcia, A.; McNeill, L. A.; McDonough, M. A.; Buck, M. R. G.; Hewitson, K. S.; Oldham, N. J.; Schofield, C. J. Chem. Commun. 2005, 5438.
  9. Stern, E.; Muccioli, G. G.; Millet, R.; Goossens, J. F.; Farce, A.; Chavatte, P. Poupaert, J. H.; Lambert, D. M.; Depreux, P.; Hénichart, J-P. J. Med. Chem. 2006, 49, 70. https://doi.org/10.1021/jm050467q
  10. Banerji, B.; Conejo-Garcia, A.; McNeill, L. A.; McDonough, M. A.; Buck, M. R. G.; Hewitson, K. S.; Oldham, N. J.; Schofield, C. J. Chem. Commun. 2005, 5438.
  11. Desforges, E.; Grysan, A; Oget, N.; Sindt, M.; Mieloszynski, J. Tetrahedron Lett. 2003, 44, 6273. https://doi.org/10.1016/S0040-4039(03)01530-2
  12. Yadav, J. S.; Reddy, B. V. S.; Baishya, G.; Narsaiah, A. Chemistry Letters 2005, 34, 102. https://doi.org/10.1246/cl.2005.102
  13. Chezal, J. M.; Moreau, E.; Delmas, G.; Gueiffier, A.; Blache, Y.; Grassy, G.; Lartigue, C.; Chavignon, O.; Teulade, J. C. Tetrahedron Lett. 2003, 44, 467. https://doi.org/10.1016/S0040-4039(02)02604-7
  14. Deinnin, F.; Buindeau, D.; Sliwa, H. Tetrahedron Lett. 1989, 30(12), 1529. https://doi.org/10.1016/S0040-4039(00)99510-8
  15. Kawato, H. C.; Nakayama, K.; Inagaki, H.; and Ohta, T. Org. Lett. 2001, 3(22), 3451. https://doi.org/10.1021/ol016394w
  16. Blanco, M. M.; Avendaño, C.; and Menéndez, J. C. Tetrahedron 1997, 53(33), 11465. https://doi.org/10.1016/S0040-4020(97)00726-6
  17. Forbes, I. T.; Johnson, C. N.; Jones, G. E.; Loudon, J.; Nicholass, J. M.; Thompson, M.; Upton, N. J. Med. Chem. 1990, 33, 2640. https://doi.org/10.1021/jm00171a046
  18. Bare, T. M.; McLaren, C. D.; Campbel1, J. B.; Firor, J. W.; Resch, J. F.; Waiters, C. P.; Salama, A. I.; Meinem, B. A.; Patel, J. B. J. Med. Chem. 1989, 32, 2561. https://doi.org/10.1021/jm00132a011
  19. Avalos, M.; Babiano, R.; Cintas, P.; Hursthouse, M. B.; Jimenez, J. L.; Light, M. E. ; Palacios, J. C.; Perez, E. M. S. Eur. J. Org. Chem. 2006, 657.
  20. Lager, E.; Andersson, P.; Nilsson, J.; Pettersson, I.; Oestergaard Nielsen, E.; Nielsen, M.; Sterner, O.; Liljefors, T. J. Med. Chem. 2006, 49(8), 2526. https://doi.org/10.1021/jm058057p
  21. Kappe, C. O. Angew. Chem., Int. Ed. 2004, 43, 6250 https://doi.org/10.1002/anie.200400655
  22. Perreux, L.; Loupy, A. Tetrahedron 2001, 57, 9199. https://doi.org/10.1016/S0040-4020(01)00905-X
  23. Kuhnert, N. Angew. Chem., Int. Ed. 2002, 41, 1863. https://doi.org/10.1002/1521-3773(20020603)41:11<1863::AID-ANIE1863>3.0.CO;2-L
  24. Strauss, C. R. Angew. Chem., Int. Ed. 2002, 41, 3589. https://doi.org/10.1002/1521-3773(20021004)41:19<3589::AID-ANIE3589>3.0.CO;2-Q
  25. Choi, J. Y.; Kim, J.; Jhung, S. H.; Kim, H. K.; Chang, J. S.; Chae, H. K. Bull. Korean. Chem. Soc. 2006, 27(10), 1523. https://doi.org/10.5012/bkcs.2006.27.10.1523
  26. Park, H. J.; Lee, J. C. Bull. Korean Chem. Soc. 2008, 29(4), 856. https://doi.org/10.5012/bkcs.2008.29.4.856
  27. Park, J. W.; Lee, K. H. Bull. Korean Chem. Soc. 2009, 30(10), 2475. https://doi.org/10.5012/bkcs.2009.30.10.2475
  28. Kim, K. W.; Lee, H. J.; Kim, C. G.; Park, M. J.; Kwon, T. W. Bull. Korean Chem. Soc. 2008, 29(3), 604. https://doi.org/10.5012/bkcs.2008.29.3.604
  29. Jo, E. A.; Ahn, J. A.; Jun, C. H. Bull. Korean Chem. Soc. 2007, 28(11), 2020. https://doi.org/10.5012/bkcs.2007.28.11.2020
  30. Kim, J. K.; Kwon, P. S.; Kwon, T. W.; Chung, S. K.; Lee, J. W. Syn. Commun. 1996, 26, 535. https://doi.org/10.1080/00397919608003646
  31. Kim, S. Y.; Kwon, P. S.; Kwon, T. W.; Chung, S. K.; Chang, Y. T. Syn. Commun. 1997, 27, 533. https://doi.org/10.1080/00397919708003323
  32. Kwon, P. S.; Kim, Y. S.; Kang, C. J.; Kwon, T. W.; Chung, S. K.; Chang, Y. T. Syn. Commun. 1997, 27, 4091. https://doi.org/10.1080/00397919708005456
  33. Loupy, A.; Song, S. J.; Sohn, S. M.; Lee, Y. M.; Kwon, T. W. J. Chem. Soc. Perkin Trans. 1 2001, 1220.
  34. Song, S. J.; Cho, S. J.; Park, D. K.; Kwon, T. W.; Jenekhe, S. A. Tetrahedron Lett. 2003, 44(2), 255. https://doi.org/10.1016/S0040-4039(02)02499-1
  35. Loupy, A.; Song, S. J.; Cho, S. J.; Park, D. K.; Kwon, T. W. Synth. Commun. 2005, 35, 79. https://doi.org/10.1081/SCC-200046503
  36. Loupy, A. Microwaves in Organic Synthesis, 2nd ed.; Wiley-VCH: Weinheim (Germany), 2006.

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