Carboxamide oximes as convenient precursors for the synthesis of pyrimidine N-oxides

Tetrahedron

Volumn 54, Issue 17, 1998, Pages 4387-4396

  Mlakar, Biserka ^a   Štefane, Bogdan ^a   Kočevar, Marijan ^a   Polanc, Slovenko ^a  

^a UNIVERSITY OF LJUBLJANA   (Slovenia)

Author keywords

[No Author keywords available]

Indexed keywords

2 BUTANONE; ACETYLACETONE; ACROLEIN DERIVATIVE; AMIDE; BUTENOLIDE; CARBONYL DERIVATIVE; OXIME DERIVATIVE; PROPANE; PYRIMIDINE DERIVATIVE; TRIFLUOROACETIC ACID;

ARTICLE; CATALYST; CHEMICAL REACTION; CHROMATOGRAPHY; OXIDATION; PRECURSOR; PRIORITY JOURNAL; SYNTHESIS;

EID: 0032560192     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(98)00152-5     Document Type: Article

References (46)

1. 1. (a) Ochiai, E. Aromatic Amine Oxides; Elsevier: Amsterdam, 1967
2. (b) Katritzky, A. R.; Lagowski, J. M. Chemistry of Heterocyclic N-Oxides; Academic: London, 1973.
3. (c) Albini, A.; Pietra, S. Heterocyclic N-Oxides, CRC: Boca Raton, 1991.
4. 2. Ref. 1c, p 273.
5. 3. (a) McCall, J. M.; TenBrink, R. E.; Ursprung, J. J. J. Org. Chem. 1975, 40, 3304-3306.
6. (b) McCall, J. M. U.S. Patent 4,287,338; Chem. Abstr. 1982, 96, 20113z.
7. (c) Catto, A.; Lo Verde, G.; Luca, C.; Graziani, G.; Nardi, D.; Casadio, S. Boll. Chim. Farm. 1982, 121, 16-26; Chem. Abstr. 1982, 97, 198165b.
8. (c) Catto, A.; Lo Verde, G.; Luca, C.; Graziani, G.; Nardi, D.; Casadio, S. Boll. Chim. Farm. 1982, 121, 16-26; Chem. Abstr. 1982, 97, 198165b.
9. (d) Reele, S. B.; Schwartz, J. H.; Spillers, C.; Seckman, C. E.; Spiro, T. E.; Royer, G. L. Curr. Ther. Res. 1984, 35, 685-694; Chem. Abstr. 1984, 101, 443a.
10. (d) Reele, S. B.; Schwartz, J. H.; Spillers, C.; Seckman, C. E.; Spiro, T. E.; Royer, G. L. Curr. Ther. Res. 1984, 35, 685-694; Chem. Abstr. 1984, 101, 443a.
11. (e) McNeil, J. J.; Louis, W. J. Handb. Hypertens. 1984, 5, 376-389; Chem. Abstr. 1985, 102, 89527x.
12. (e) McNeil, J. J.; Louis, W. J. Handb. Hypertens. 1984, 5, 376-389; Chem. Abstr. 1985, 102, 89527x.
13. 4. Murad, S.; Tennant, M. C.; Pinnell, S. R. Arch. Biochem. Biophys. 1992, 292, 234-238.
14. 5. Griffin, R. J.; Stevens, M. F. G. J. Chem. Soc. Perkin Trans 1 1994, 3311-3318.
15. 6. Rey-Bellet, G.; Reiner, R.; Schwartz, D. E. Ger. Offen. 2,026,997; Chem. Abstr. 1971, 74, 76443v.
16. 7. (a) Rumsfield, J. A.; West, D. P.; Fiedler-Weiss, V. C. Clin. Pharm. 1987, 6, 386-392.
17. (b) Kvedar, J. C.; Baden, H. P. Pharmacotheraphy 1987, 7, 191-197.
18. (c) Dufetel, D.; Estradier, F.; Hocquaux, M. Eur. Pat. Appl. EP 459,890; Chem. Abstr. 1992, 116, 135998r.
19. (d) Otomo, S. Juntendo Igaku 1992, 37, 606-612; Chem. Abstr. 1992, 117, 142743c.
20. (d) Otomo, S. Juntendo Igaku 1992, 37, 606-612; Chem. Abstr. 1992, 117, 142743c.
21. 8. Rhie, S. Y.; Ryu, E. K. Heterocycles 1995, 41, 323-328.
22. 9. Yamanaka, H.; Sakamoto, T.; Niitsuma, S. Heterocycles 1990, 31, 923-963.
23. 10 Kočevar, M.; Mlakar, B.; Perdih, M.; Petrič, A.; Polanc, S.; Verček, B. Tetrahedron Lett. 1992, 33, 2195-2198.
24. 11. For a general review on the preparation of 1,2,4-oxadiazoles, see Jochims, J. C. In Comprehensive Heterocyclic Chemistry II; Storr, R. C., Ed.; Pergamon: Oxford, 1996; Vol. 4, pp 179-228, and references therein.
25. 12. (a) Romo, J.; Rodriguez-Hahn, L.; Jiménez, M. Can. J. Chem. 1968, 46, 2807-2815.
26. (b) Tikhonov, A. Ya.; Volodarskii, L. B. Tetrahedron Lett. 1975, 2721-2724.
27. (c) Tikhonov, A. Ya.; Volodarskii, L. B. Khim. Geterotsikl. Soedin. 1977, 252-258; Chem. Abstr. 1977, 87, 5901a.
28. (c) Tikhonov, A. Ya.; Volodarskii, L. B. Khim. Geterotsikl. Soedin. 1977, 252-258; Chem. Abstr. 1977, 87, 5901a.
29. (d) Tikhonov, A. Ya.; Sedova, V. F.; Volodarskii, L. B.; Mamaev, V. P. Khim. Geterotsikl. Soedin. 1981, 526-529; Chem. Abstr. 1981, 95, 80878a.
30. (d) Tikhonov, A. Ya.; Sedova, V. F.; Volodarskii, L. B.; Mamaev, V. P. Khim. Geterotsikl. Soedin. 1981, 526-529; Chem. Abstr. 1981, 95, 80878a.
31. (e) Tikhonov, A. Ya.; Volodarskii, L. B.; Vakolova, O. A.; Podgornaya, M. I. Khim. Geterotsikl. Soedin. 1981, 110-116; Chem. Abstr. 1981, 95, 7201m.
32. (e) Tikhonov, A. Ya.; Volodarskii, L. B.; Vakolova, O. A.; Podgornaya, M. I. Khim. Geterotsikl. Soedin. 1981, 110-116; Chem. Abstr. 1981, 95, 7201m.
33. 13. (a) Kasuga, K.; Hirobe, M.; Okamoto, T. Chem. Pharm. Bull. 1974, 22, 1814-1826.
34. (b) Roeterdink, F.; van der Plas, H. C. Tetrahedron Lett. 1976, 3337-3338.
35. (c) Kashima, C.; Katoh, A.; Yokota, Y., Omote, Y. Chem. Pharm. Bull. 1981, 29, 2516-2519.
36. (d) Zvilichovsky, G.; David, M. J. Org. Chem. 1983, 48, 575-579.
37. (e) Vivona, N.; Buscemi, S.; Frenna, V.; Ruccia, M. J. Chem. Soc. Perkin Trans, 1 1986, 17-19.
38. (f) Buscemi, S.; Macaluso, G.; Frenna, V.; Vivona, N. J. Heterocyclic Chem. 1986, 23, 1175-1177.
39. 14 (a) Sakamoto, T.; Niitsuma, S.; Mizugaki, M.; Yamanaka, H. Heterocycles 1977, 8, 257-262.
40. (b) Sakamoto, T.; Niitsuma, S.; Mizugaki, M.; Yamanaka, H. Chem. Pharm. Bull. 1979, 27, 2653-2660.
41. 15 Tani, H.; Nakamura, K. Japan Pat. 7411707; Chem. Abstr. 1974, 81, 91551s.
42. 16. Steinkopf, W.; Bohrmann, L. Chem. Ber. 1907, 40, 1633-1643.
43. 17. Stephenson, L.; Warburton, W. K.; Wilson, M. J. J. Chem. Soc. (C) 1969, 861-864.
44. 18. Street, L. J.; Baker, R.; Castro, J. L.; Chambers, M. S.; Guiblin, A. R.; Hobbs, S. C.; Matassa, V. G.; Reeve, A. J.; Beer, M. S.; Middlemiss D. N.; Noble, A. J.; Stanton, J. A.; Scholey, K.; Hargreaves, R. J. J. Med. Chem. 1993, 36, 1529-1538.
45. 19. Bata, I.; Korbonits, D.; Kolonits, P.; Podányi, B.; Takácsy-Erös, T.; Simon, K. Chem. Ber. 1993, 126, 1835-1841.
46. 20. Clark, K. J. Chem. Soc. 1954, 4251-4253.