Synthesis of multi-substituted 2-iminopyridine by conjugate addition of ethyl cyanoacetate derivatives to alkynyl imines

European Journal of Organic Chemistry

Volumn , Issue 8, 2008, Pages 1411-1417

  Hachiya, Iwao ^a   Minami, Yushi ^a   Aramaki, Tetsuya ^a   Shimizu, Makoto ^a  

^a MIE UNIVERSITY   (Japan)

Author keywords

Alkynes; Amines; Conjugate addition; Imines; Pyridine; Ring opening

Indexed keywords

EID: 53749096500     PISSN: 1434193X     EISSN: 10990690     Source Type: Journal    
DOI: 10.1002/ejoc.200701039     Document Type: Article

References (35)

1. a) C. Hamdouchi, J. de Blas, M. de Prado, J. Gruber, B. A. Heinz, L. Vance, J. Med. Chem. 1999, 42, 50-59;
2. b) M. A. Ismail, R. Brun, T. Wenzler, F. A. Tanious, W. D. Wilson, D. W. Boykin, J. Med. Chem. 2004, 47, 3658-3664.
3. A. H. Abadi, H. A. Al-Khamees, Arch. Pharmacol. Med. Chem. 1998, 331, 319-324.
4. a) A. Z. Schultz, Chem. Rev. 1973, 73, 385-405;
5. b) D. P. Curran, H. Liu, J. Am. Chem. Soc. 1992, 114, 5863-5864;
6. c) A. P. Kozikowski, G. Campiani, L.-Q. Sun, S. Wang, A. Saxena, B. P. Doctor, J. Am. Chem. Soc. 1996, 118, 11357-11362;
7. d) D. R. Williams, P. D. Lowder, Y.-G. Gu, Tetrahedron Lett. 1997, 38, 327-330;
8. e) M.-L. Bennasar, E. Zulaica, C. Juan, Y. Alonso, J. Bosch, J. Org. Chem. 2002, 67, 7465-7474;
9. f) G. Semple, B.-M. Andersson, V. Chhajlani, J. Georgsson, M. J. Johannsson, A. Rosenquist, L. Swanson, Bioorg. Med. Chem. Lett. 2003, 13, 1141-1145;
10. g) J. J. Parlow, M. S. South, Tetrahedron 2003, 59, 7695-7701;
11. h) J. J. Palow, R. G. Kurumbail, R. A. Stegeman, A. M. Stevens, W. C. Stallings, M. S. South, J. Med. Chem. 2003, 46, 4696-4701;
12. i) P. Fossa, G. Menozzi, P. Dorigo, M. Floreani, L. Mosti, Bioorg. Med. Chem. 2003, 11, 4749-4759.
13. a) G. Ege, H. O. Frey, E. Schuck, Synthesis 1979, 376-378;
14. b) A. H. H. Elghandour, M. M. M. Ramiz, M. H. Elnagdi, Synthesis 1989, 775-777;
15. c) Y. M. Elkholy, A. W. Erian, Heteroat. Chem. 2003, 14, 503-508;
16. d) A.-Z. A.-A. Elassar, Heteroat. Chem. 2004, 15, 293-299.
17. a) P. Hong, H. Yamazaki, Tetrahedron Lett. 1977, 18, 1333-1336;
18. b) H. Hoberg, G. Burkhart, Synthesis 1979, 525-526;
19. c) P. Diversi, G. Ingrosso, A. Lucherini, S. Malquori, J. Mol. Catal. 1987, 40, 267-280;
20. d) D. D. Young, A. Deiters, Angew. Chem. Int. Ed. 2007, 46, 5187-5190.
21. T. Takahashi, F.-U. Tsai, Y. Li, H. Wang, Y. Kondo, M. Yamanaka, K. Nakajima, M. Korota, J. Am. Chem. Soc. 2002, 124, 5059-5067.
22. a) I. Hachiya, K. Ogura, M. Shimizu, Org. Lett. 2002, 4, 2755-2757;
23. b) I. Hachiya, K. Ogura, M. Shimizu, Synthesis 2004, 1349-1352.
24. a) I. Hachiya, S. Fukushima, M. Shimizu, Heterocycles 2006, 69, 43-48;
25. for the synthesis of bicyclic compounds containing a 2-pyridone structure by addition reactions of malonic esters to alkynylpyridines, pyrimidine, and thiazoles, see: b) I. Hachiya, M. Atarashi, M. Shimizu, Heterocycles 2006, 67, 523-528.
26. For examples of the transformation of 2-iminopyridines into 2-aminopyridines, see: a) R. Adams, I. J. Pachter, J. Am. Chem. Soc. 1952, 74, 4906-4909;
27. b) K. Hartke, M. Sauebier, W. F. Richter, Arch. Pharm. 1992, 325, 279-284.
28. For recent examples, see: a) S. A. S. Ghozlan, A. Z. A. Hassanien, Tetrahedron 2002, 58, 9423-9429;
29. b) O. S. Moustafa, R. A. Ahmad, Phosphorus, Sulfur Silicon Relat. Elem. 2003, 178, 475-484;
30. c) J. L. Marco, C. del los Ríos, A. G. García, M. Villarroya, M. C. Carreiras, C. Martins, A. Eleutério, A. Morreale, M. Orozco, F. J. Luque, Bioorg. Med. Chem. 2004, 12, 2199-2218;
31. d) R. León, J. Marco-Contelles, A. G. García, M. Villarroya, Bioorg. Med. Chem. 2005, 13, 1167-1175;
32. e) A.-G. E. Amr, A. M. Mohamed, S. F. Mohamed, N. A. Abel-Hafez, A. E.-F. G. Hammam, Bioorg. Med. Chem. 2006, 14, 5481-5488.
33. K. Okuro, M. Furuune, M. Miura, M. Nomura, J. Org. Chem. 1993, 58, 7606-7607.
34. K. Terao, A. Toshimitsu, S. Uemura, J. Chem. Soc. Perkin Trans. 1 1986, 1837-1843.
35. B. G. Van den Hoven, H. Alper, J. Am. Chem. Soc. 2001, 123, 1017-1022.