Nucleophilic vinylic substitution (SNV) of activated alkoxymethylene derivatives with 6-aminoquinoxaline

European Journal of Organic Chemistry

Volumn , Issue 22, 2005, Pages 4870-4878

  Saloň, Jozef ^a   Milata, Viktor ^a   Gatial, Anton ^a   Prónayová, Nadežda ^a   Leško, Ján ^a   Černuchová, Petra ^a   Rappoport, Zvi ^b   Vo Thanh, Giang ^c   Loupy, André ^c  

^a SLOVAK UNIVERSITY OF TECHNOLOGY   (Slovakia)

^b HEBREW UNIVERSITY OF JERUSALEM   (Israel)

^c UNIVERSITÉ PARIS SUD   (France)

Author keywords

Alkoxymethylene compounds; Enol ethers; Molecular calculations; Nucleophilic vinylic substitution (SNV) mechanism; Quinoxalines

Indexed keywords

EID: 27844560670     PISSN: 1434193X     EISSN: None     Source Type: Journal    
DOI: 10.1002/ejoc.200500298     Document Type: Article

References (53)

1. A. R. Katritzky, A. J. Boulton, Advances in Heterocyclic Chemistry (Ed.: A. R. Katritzky), Academic Press, San Diego, USA, 1978, vol. 22, p. 368.
2. a) M. Nagao, M. Honda, Y. Seino, T. Yahagi, T. Sugimura, Cancer Lett. 1977, 2, 221-239;
3. b) K. Wakabayashi, M. Nagao, H. Esumi, T. Sugimura, Cancer Res. (Suppl) 1992, 52, 2092-2098:
4. c) Food Borne Carcinogens (Eds.: M. Nagao, T. Sugimura), Wiley, Chichester, 2000;
5. d) V. Milata, Advances in Heterocyclic Chemistrv (Ed.: A. R. Katritzky), Academic Press, San Diego, 2001, vol. 78, p. 189;
6. e) F. T. Hatch, M. E. Colvin, E. T. Seidl, Environ. Mol. Mutagen. 1996, 27, 314- 330.
7. V. Milata, Aldrichim. Acta 2001, 34, 20-27.
8. G. Y. Lesher, E. J. Froehlich, M. D. Gruett, J. H. Bailey, R. P. Brundage, J. Med. Pharm. Chem. 1962, 1063-1064.
9. V. D. Dyachenko, R. P. Tkachev, Russ. J. Org. Chem. 2003, 39, 757-793.
10. V. P. Litvinov, Ya. Yu. Yakunin, V. D. Dyachenko, Chem. Heterocycl. Compds. 2001, 37, 37-76.
11. K. S. Sardesai, Bombay Technol. 1957/58, 8, 36-40;
12. Chem. Abstr. 1960, 54, 4378a.
13. F. Freeman, Synthesis 1981, 925-954.
14. I. Hermecz, G. Keresztúri, L. Vasvári-Debreczy, Advances in Heterocyclic Chemistry (Ed.: A. R. Katritzky), Academic Press, San Diego, 1992, vol. 54.
15. A. Fry, Organic Reaction Mechanisms (Eds.: A. C. Knipe, W. E. Watts), J. Wiley & Sons, Chichester, 1987, chapter 13, p. 387.
16. S. M. McElvain, K. Rorig, J. Am. Chem. Soc. 1948, 70, 1820-1826.
17. M. Freifelder, J. Am. Chem. Soc. 1960, 82, 2386-2389.
18. Z. Rappoport, S. Patai, The Chemistry of Alkenes (Ed.: S. Patai), Wiley, Chichester, 1964, chapter 8, p. 469.
19. H. Shenhav, Z. Rappoport, S. Patai, J. Chem. Soc. B 1970, 469-475.
20. a) H. K. Oh, J. H. Yang, D. D. Sung, I. Lee, J. Chem. Soc., Perkin Trans. 2 2000, 101-106;
21. b) H. K. Oh, J. H. Yang, H. W. Lee, I. Lee, J. Org. Chem. 2000, 65, 2188-2191;
22. H. K. Oh, J. H. Yang, H. W. Lee, I. Lee, J. Org. Chem. 2000, 65, 5391-5395;
23. c) H. K. Oh, T. S. Kim, H. W. Lee, I. Lee, J. Chem. Soc. Perkin Trans. 2 2002, 282-286;
24. d) H. K. Oh, J. H. Yang, Y. H. Hwang, H. W. Lee, I. Lee, J. Bull. Korean Chem. Soc. 2002, 23, 221.
25. Z. Rappoport, Adv. Phys. Org. Chem. 1969, 7, 1-49.
26. Z. Rappoport. Recl. Trav. Chim. Pays-Bas 1985, 104, 309-349.
27. J. Kuthan, D. Ilavský, J. Krechl, P. Trška, Collect. Czech. Chem. Commun. 1979, 44, 1423-1433.
28. Z. Rappoport, Recl. Trav. Chim. Pays-Bas 1985, 104, 309-349.
29. a) V. Milata, D. Ilavský, I. Goljer, J. Leško, M. Chahinian, E. Henry-Basch, Collect. Czech. Chem. Commun. 1990, 55, 1038-1048;
30. b) J. Saloň, V. Milata, N. Prónayová, J. Leško, Monatsh. Chem. 2000, 131, 293-299.
31. a) C. F. Bernasconi, R. J. Ketner, S. D. Brown, X. Chen, Z. Rappoport, J. Org. Chem. 1999, 64, 8829-8839;
32. b) C. F. Bernasconi, A. E. Leyes, Z. Rappoport, J. Org. Chem. 1999, 64, 2897-2902;
33. c) C. F. Bernasconi, A. E. Leyes, I. Eventova, Z. Rappoport, J. Am. Chem. Soc. 1995, 117, 1703-1711;
34. d) C. F. Bernasconi, D. F. Schuck, R. J. Ketner, I. Eventova, Z. Rappoport, J. Am. Chem. Soc. 1995, 117, 2719-2725;
35. e) C. F. Bernasconi, R. J. Ketner, X. Chen, Z. Rappoport, J. Am. Chem. Soc. 1998, 120, 7461-7468.
36. a) Z. Rappoport, P. Peled, J. Chem. Soc., Perkin Trans. 2 1973, 616-625;
37. b) Z. Rappoport, S. Hoz, J. Chem. Soc., Perkin Trans. 2 1975, 272-281;
38. c) Z. Rappoport, A. Topol, J. Chem. Soc., Perkin Trans. 2 1975, 863-874;
39. Z. Rappoport, A. Topol, J. Am. Chem. Soc. 1980, 102, 406-407;
40. d) Z. Rappoport, P. Peled, J. Am. Chem. Soc. 1979, 101, 2682-2693.
41. a) T. Okuyama, G. Lodder, Adv. Phys. Org. Chem. 2002, 37, 1-56;
42. b) C. K. Kim, K. H. Hyun, C. K. Kim, I. Lee, J. Am. Chem. Soc. 2000, 122, 2294-2299;
43. c) J. J. Shiers, M. Shipman, J. F. Hayes, A. M. Z. Slawin, J. Am. Chem. Soc. 2004, 126, 6868-6869;
44. d) K. Ando, M. Kitamura, K. Miura, K. Narasaka, Org. Lett. 2004, 6, 2461-2464.
45. F. Jourdain, J. C. Pommelet, Synth. Commun. 1997, 27, 483-492.
46. a) B. Couchouron, J. Le Saint, P. Courtot, Bull. Soc. Chim. Fr. 1983, 3-4, 66-72;
47. b) M. Michalik, Z. Chem. 1985, 25, 287-288;
48. c) M. Michalik, J. Prakt. Chem. 1985, 327, 908-916.
49. M. J. Frisch, G. W. Trucks, H. B. Schlegel, P. M. W. Gill, B. G. Johnson, M. A. Robb, J. R. Cheeseman, T. Keith, G. A. Petersson, J. A. Montgomery, K. Raghavachari, M. A. Al-Laham, V. G. Zakrzewski, J. V. Ortiz, J. B. Foresman, J. Cioslowski, B. B. Stefanov, A. Nanayakkara, M. Challacombe, C. Y. Peng, P. Y. Ayala, W. Chen, M. W. Wong, J. L. Andres, E. S. Replogle, R. Gomperts, R. L. Martin, D. J. Fox, J. S. Binkley, D. J. Defrees, J. Baker, J. J. P. Stewart, M. Head-Gordon, C. Gonzales and J. A. Pople, Gaussian 94 (Revision D.3), Gaussian, Inc., Pittsburgh, PA, 1995.
50. MOPAC6: J. J. P. Stewart, QCPE Bull. 1983, 3, 101.
51. J. Ohmori, S. Sakamoto, H. Kupota, M. Shimizu-Sasamata, M. Okada, S. Kawasaki, K. Hidaka, J. Togami, T. Furuya, K. Midase, J. Med. Chem. 1994, 37, 467-475.
52. J. Saloň, V. Milata, N. Prónayová, J. Leško, Monatsh. Chem. 2000, 131, 293-299.
53. D. F. Gloster, L. Cincotta, J. Heterocycl. Chem. 1999, 36, 25-32.