Solvent-free michael addition between EMME and secondary amine under focused microwave irradiation

Bulletin of the Korean Chemical Society

Volumn 31, Issue 5, 2010, Pages 1155-1158

  Kim, Ki Won ^a   Lee, Hee Jung ^a   Jo, Jeong Im ^a   Kwon, Tae Woo ^a  

^a Kyungsung University   (South Korea)

Author keywords

Diethyl 2 ((diaryl or dialkyl lamino) methylene) malonate; Diethyl ethoxymethylenemalonate; Focused microwave assisted irradiation; Secondary amines; Solvent free Michael addition

Indexed keywords

DIETHYL ETHOXYMETHYLENEMALONATE; FOCUSED MICROWAVES; MALONATES; MICHAEL ADDITIONS; SECONDARY AMINES; SOLVENT FREE;

ADDITION REACTIONS; AMINES; IRRADIATION; SOLVENTS;

MICROWAVE IRRADIATION;

EID: 77952645543     PISSN: 02532964     EISSN: 12295949     Source Type: Journal    
DOI: 10.5012/bkcs.2010.31.5.1155     Document Type: Article

References (36)

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.
3. Koga, H.; Ito, A.; Murayama, S.; Suzue, S.; Irikura, T. J. Med. Chem. 1980, 23(12), 1358.
4. Hayakawa, I.; Hiramitsu, T.; Tanaka, Y. Chem. Pharm. Bull. 1984, 32, 4907.
5. Atarashi, S.; Yokahama, S.; Yamazaki, K.; Sakano, K.; Imamura, M.; Hayakawa, I. Chem. Pharm. Bull. 1987, 35, 1896.
6. Santilli, A. A.; Bruce, W. F.; Osdene, T. S. J. Med. Chem. 1963, 7(1), 68.
7. Steck, E. A. J. Org. Chem. 1962, 27, 306.
8. 3.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.
10. 4.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.
12. Yadav, J. S.; Reddy, B. V. S.; Baishya, G.; Narsaiah, A. Chemistry Letters 2005, 34, 102.
13. 5.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.
14. Deinnin, F.; Buindeau, D.; Sliwa, H. Tetrahedron Lett. 1989, 30(12), 1529.
15. 6.Kawato, H. C.; Nakayama, K.; Inagaki, H.; and Ohta, T. Org. Lett. 2001, 3(22), 3451.
16. Blanco, M. M.; Avendaño, C.; and Menéndez, J. C. Tetrahedron 1997, 53(33), 11465.
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.
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.
19. Ávalos, M.; Babiano, R.; Cintas, P.; Hursthouse, M. B.; Jiménez, J. L.; Light, M. E. ; Palacios, J. C.; Pérez, 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.
21. 9.Kappe, C. O. Angew. Chem., Int. Ed. 2004, 43, 6250 and references therein.
22. erreux, L.; Loupy, A. Tetrahedron 2001, 57, 9199.
23. Kuhnert, N. Angew. Chem., Int. Ed. 2002, 41, 1863.
24. Strauss, C. R. Angew. Chem., Int. Ed. 2002, 41, 3589.
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.
26. Park, H. J.; Lee, J. C. Bull. Korean Chem. Soc. 2008, 29(4), 856.
27. Park, J. W.; Lee, K. H. Bull. Korean Chem. Soc. 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.
29. Jo, E. A.; Ahn, J. A.; Jun, C. H. Bull. Korean Chem. Soc. 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.
31. Kim, S. Y.; Kwon, P. S.; Kwon, T. W.; Chung, S. K.; Chang, Y. T. Syn. Commun. 1997, 27, 533.
32. Kwon, P. S.; Kim, Y. S.; Kang, C. J.; Kwon, T. W.; Chung, S. K.; Chang, Y. T. Syn. Commun. 1997, 27, 4091.
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.
35. Loupy, A.; Song, S. J.; Cho, S. J.; Park, D. K.; Kwon, T. W. Synth. Commun. 2005, 35, 79.
36. Loupy, A. Microwaves in Organic Synthesis, 2nd ed.; Wiley-VCH: Weinheim (Germany), 2006.