Palladium-catalyzed amination and amidation of benzo-fused bromine-containing heterocycles

Russian Journal of Organic Chemistry

Volumn 41, Issue 6, 2005, Pages 860-874

  Sergeev, A G ^a   Artamkina, G A ^a   Velezheva, V S ^b   Fedorova, I N ^b   Beletskaya, I P ^a  

^a MOSCOW STATE UNIVERSITY   (Russian Federation)

^b A N NESMEYANOV INSTITUTE OF ORGANOELEMENT COMPOUNDS   (Russian Federation)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 23944482986     PISSN: 10704280     EISSN: None     Source Type: Journal    
DOI: 10.1007/s11178-005-0257-0     Document Type: Article

References (50)

1. Kleemann, A. and Engel, J., Pharmazeutische Wirkstoffe: Synthesen, Patente, Anwendungen, Stuttgart: Thieme, 1978.
2. Mashkovskii, M.D., Lekarstvennye sredstva (Drugs), Moscow: Meditsina, 2002, vols. 1, 2.
3. Akalaeva, T.V., Bokanov, A.I., Ivanov, P.Yu., Nikolaeva, I.S., Pushkina, T.V., Fomina, A.N., and Shvedov, V.I., Khim.-Farm. Zh., 1989, no. 3, p. 299.
4. Akalaeva, T.V., Amel'kin, L.Yu., Baklanova, O.V., Bokanov, A.I., Ivanov, P.Yu., Padeiskaya, E.N., Radkevich, T.P., Filitis, L.N., and Shvedov, V.I., Khim.-Farm. Zh., 1990, no. 11, p. 46.
5. Filitis, L.N., Akalaeva, T.V., Amel'kin, L.Yu., Bokanov, A.I., Ivanov, P.Yu., and Shvedov, V.I., Khim.-Farm. Zh., 1988, no. 10, p. 1217.
6. Mahboobi, S., Kuhr, S., and Meindl, M., Arch. Pharm., 1994, vol. 327, p. 611.
7. Asselin, A.A., Humber, L.G., and Komlossy, J., J. Med. Chem., 1976, vol. 19, p. 792.
8. Sowmithran, D. and Rajendra Prasad, K.J., Heterocycles, 1986, vol. 24, p. 711;
9. Sowmithran, D. and Rajendra Prasad, K.J., Indian J. Chem., Sect. B, 1987, vol. 26, p. 277;
10. Bhattacharyya, P. and Iash, S.S., Indian J. Chem., Sect. B, 1986, vol. 25, p. 1056;
11. Sekar, H., Vanitha, S., and Rajendra Prasad, K.J., Z. Naturforsch., 1994, vol. 49, p. 687;
12. Sekar, H. and Rajendra Prasad, K.J., Indian J. Chem., Sect. B, 1998, vol. 37, p. 314.
13. Balamurali, R. and Rajendra Prasad, K.J., Z. Naturforsch., Teil B, 1999, vol. 54, p. 1618;
14. Balamurali, R. and Rajendra Prasad, K.J., Heterocycl. Commun., 2000, vol. 6, p. 153;
15. Masaguer, C.F., Ravina, E., Fontenla, J.A., Brea, J., Tristan, H., and Loza, M.I., Eur. J. Med. Chem., 2000, vol. 35, p. 83;
16. Balamurali, R. and Rajendra Prasad, K.J., Indian J. Chem., Sect. B, 2001, vol. 40, p. 139;
17. Balamurali, R. and Rajendra Prasad, K.J., Heterocycl. Commun., 2001, vol. 7, p. 149;
18. Balamurali, R. and Rajendra Prasad, K.J., Farmaco, 2001, vol. 56, p. 229.
19. Shvedov, V.I., Altukhova, L.B., and Grinev, A.N., Khim.-Farm. Zh., 1967, no. 3, p. 25;
20. Shvedov, V.I., Altukhova, L.B., Andreeva, N.I., Mashkovskii, D.M., and Grinev, A.N., Khim.-Farm. Zh., 1972, no. 10, p. 14;
21. Ivanov, P.Yu., Alekseeva, L.M., Bokanov, A.I., Shvedov, V.I., and Sheinker, Yu.N., Khim.-Farm. Zh., 1987, no. 1, p. 71.
22. Engler, T.A., LaTessa, K.O., Iyengar, R., Chai, W., and Agrios, K., Bioorg. Med. Chem., 1996, vol. 4, no. 10, p. 1755.
23. Bourgery, G., Dostert, P., Lacour, A., Langlois, M., Pourrias, B., and Tisne-Versailles, J., J. Med. Chem., 1981, vol. 24, no. 2, p. 159.
24. Effland, C.R., Klein, J.T., Martin, L.L., Shutske, GM., Kapples, K.J., and Tomer, J.D., US Patent no. 5328920, 1994; Chem. Abstr., 1995, vol. 123, no. 83210a.
25. Wolfe, J.P., Wagaw, S., Marcoux, J.-F., and Buchwald, S.L., Acc. Chem. Res., 1998, vol. 31, p. 805;
26. Yang, B.H. and Buchwald, S.L., J. Organomet. Chem., 1999, vol. 576, p. 125;
27. Hartwig, J.F., Angew. Chem., Int. Ed., 1998, vol. 37, p. 2046;
28. Wolfe, J.P, Tomori, H., Sadighi, J.P., Yin, J., and Buchwald, S.L., J. Org. Chem., 2000, vol. 65, p. 1158.
29. Wolfe, J.P. and Buchwald, S.L., J. Org. Chem., 2000, vol. 65, p. 1144.
30. Hooper, M.W., Utsunomiya, M., and Hartwig, J.F., J. Org. Chem., 2003, vol. 68, p. 2861.
31. Abouabdellah, A. and Dodd, R.H., Tetrahedron Lett., 1998, vol. 39, p. 2119;
32. Malapel-Andrieu, B. and Mérour, J.-Y., Tetrahedron, 1998, vol. 54, p. 11095.
33. He, F., Foxman, B.M., and Snider, B.B., J. Am. Chem. Soc., 1998, vol. 120, p. 6417.
34. Yin, J. and Buchwald, S.L., J. Am. Chem. Soc., 2002, vol. 124, p. 6043.
35. Artamkina, G.A., Sergeev, A.G., and Beletskaya, I.P., Tetrahedron Lett., 2001, vol. 42, p. 4381;
36. Artamkina, G.A., Sergeev, A.G., and Beletskaya, I.P., Russ. J. Org. Chem., 2002, vol. 38, p. 538.
37. Sergeev, A.G., Artamkina, G.A., and Beletskaya, I.P., Tetrahedron Lett., 2003, vol. 44, p. 4719;
38. Sergeev, A.G., Artamkina, G.A., and Beletskaya, I.P., Russ. J. Org. Chem., 2003, vol. 39, p. 1741.
39. Kong, K-C. and Cheng, C.-H., J. Am. Chem. Soc., 1991, vol. 113, p. 6313.
40. Ishii, Y., Ann. N.Y. Acad. Sci., 1972, vol. 239, p. 114;
41. Ukai, T., Kawazura, H., and Ishii, Y., J. Organomet. Chem., 1974, vol. 65, p. 253.
42. Kranenburg, M., van der Burgt, Y.E.M., Kamer, P.C.J., and van Leeuwen, P.W.N.M., Organometallics, 1995, vol. 14, p. 3081;
43. Hillebrand, S., Bruckmann, J., and Krüger, M.W., Tetrahedron Lett., 1995, vol. 36, p. 75.
44. Ostrovskaya, V.M. and Gorker, I.A., Metody polucheniya khimicheskikh reaktivov i preparatov (Methods of Preparation of Chemicals), Moscow: IREA, 1967, vol. 17, p. 36.
45. Torii, S., Yamanaka, T., and Tanaka, H., J. Org. Chem., 1978, vol. 43, p. 2882.
46. Noland, W.E. and Reich, C., J. Org. Chem., 1967, vol. 32, p. 828.
47. Trofimov, F.A., Tsyshkova, N.G., and Grinev, A.N., Khim. Geterotsikl. Soedin., 1973, no. 3, p. 308.
48. Grinev, A.N., Zotova, S.A., Mukhanova, T.I., Lyubchanskaya, V.M., Shvarts, GYa., Syubaev, R.D., and Mashkovskii, M.D., Khim.-Farm. Zh., 1982, no. 3, p. 291.
49. Grinev, A.N., Zotova, S.A., Gololobova, T.M., and Stolyarchuk, V.A., Khim.-Farm. Zh., 1982, no. 12, p. 1470.
50. Bender, H.R., Beyerle, R., Keyl, K.-H., Greve, H.G., and Reh, K., US Patent no. 4271073, 1981; Chem. Abstr., 1981, vol. 95, no. 115292a.