A practical and user-friendly method for the selenium-free one-step preparation of 1,2-diketones and their monoxime analogs

Synlett

Volumn , Issue 13, 2004, Pages 2315-2318

  Rüedi, Georg ^a   Oberli, Matthias A ^a   Nagel, Matthias ^b   Weymuth, Christophe ^a   Hansen, Hans Jürgen ^a  

^a UNIVERSITY OF ZURICH   (Switzerland)

^b SWISS FEDERAL LABORATORIES FOR MATERIALS SCIENCE AND TECHNOLOGY   (Switzerland)

Author keywords

oximation; 1,2 Diketones; 1,2 Dione monoximes; Nitrosation; Oxidations

Indexed keywords

1,2 DIKETONE; 1,2 DIONE OXIME; DIKETONE; OXIME DERIVATIVE; SELENIUM; UNCLASSIFIED DRUG;

ALPHA OXIMATION; ARTICLE; CHEMICAL REACTION; NITROSATION; OXIDATION; SYNTHESIS;

EID: 8644263988     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2004-832815     Document Type: Article

References (36)

1. (a) Wright, M. W.; Welker, M. J. Org. Chem. 1996, 61, 133.
2. (b) Trost, B. M.; Schroeder, G. M. J. Am. Chem. Soc. 2000, 122, 3785.
3. (a) Angelastro, M. R.; Mehdi, S.; Burkhart, J. P.; Peet, N. P.; Bey, P. J. Med. Chem. 1990, 33, 11.
4. (b) Khan, F. A.; Prabhudas, B.; Dash, J.; Sahu, N. J. Am. Chem. Soc. 2000, 122, 9558.
5. (c) Nicolaou, K. C.; Gray, D. L. F.; Tae, J. J. Am. Chem. Soc. 2003, 126, 613.
6. (a) Rao, T. B.; Rao, J. M. Synth. Commun. 1993, 23, 1527.
7. (b) Suda, K.; Baba, K.; Nakajima, S.; Takanami, T. Chem. Commun. 2002, 2570.
8. (c) Chang, C.-L.; Kumar, M. P.; Liu, R.-S. J. Org. Chem. 2004, 69, 2793.
9. (a) Williams, D. R.; Robinson, L. A.; Amato, G. S.; Osterhout, M. H. J. Org. Chem. 1992, 57, 3740.
10. (b) Chang, S.; Lee, M.; Ko, S.; Lee, P. H. Synth. Commun. 2002, 32, 1279.
11. (c) Rao, T. V.; Dongre, R. S.; Jain, S. L.; Sain, B. Synth. Commun. 2002, 32, 2637.
12. (a) Khurana, J. M.; Kandpal, B. M. Tetrahedron Lett. 2003, 44, 4909.
13. (b) Jain, S. L.; Sharma, V. B.; Sain, B. Tetrahedron Lett. 2004, 45, 1233.
14. (a) Yusubov, M. S.; Filimonov, V. D.; Vasilyeva, V. P.; Chi, K. Synthesis 1995, 1234.
15. (b) Rogatchov, V. O.; Filimonov, V. D.; Yusubov, M. S. Synthesis 2001, 1001.
16. (c) Yusubov, M. S.; Zholobova, G. A.; Vasilevsky, S. F.; Tretyakov, E. V.; Knight, D. W. Tetrahedron 2002, 58, 1607.
17. Antoniotti, S.; Dunach, E. Chem. Commun. 2001, 2566.
18. For recent transition and lanthanide metal-mediated examples, see: (a) Baruah, B.; Bourah, A.; Prajapati, D.; Sandhu, J. S. Tetrahedron Lett. 1997, 38, 6717.
19. (b) Back, H. S.; Lee, S. J.; Yoo, B. W.; Ko, J. J.; Kim, S. H.; Kim, J. H. Tetrahedron Lett. 2000, 41, 8097.
20. (c) Saikia, P.; Laskar, D. D.; Prajapati, D.; Sandhu, J. S. Tetrahedron Lett. 2002, 43, 7525.
21. (d) Wang, X.; Zhang, Y. Tetrahedron 2003, 59, 4201.
22. For recent electroreductive coupling reactions, see: (a) Hebri, H.; Dunach, E.; Heintz, M.; Troupel, M.; Perichon, P. Synlett 1991, 901.
23. (b) Kashimura, S.; Murai, Y.; Ishifune, M.; Masuda, H.; Murase, H.; Shono, T. Tetrahedron Lett. 1995, 36, 4805.
24. (c) Kise, N.; Ueda, N. Bull. Chem. Soc. Jpn. 2001, 74, 755.
25. (d) Heintz, M.; Devaud, M.; Hebri, H.; Dunach, E.; Troupel, M. Tetrahedron 1993, 49, 2249.
26. Fileti, M.; Ponzio, G. Gazz. Chim. Ital. 1895, 25, 239.
27. (a) Campillo, N.; Garcia, C.; Goya, P.; Paez, J. A.; Carrasco, E.; Grau, M. J. Med. Chem. 1999, 42, 1698.
28. (b) Fröhlich, L. G.; Kotsonis, P.; Traub, H.; Tagavi-Moghadam, S.; Al-Masoudi, M.; Hoffmann, H.; Strobel, H.; Matter, H.; Pfleiderer, W.; Schmidt, H. H. H. W. J. Med. Chem. 1999, 42, 4108.
29. 1H NMR of 2 showed a significantly low field shifted singlet at δ = 8.53 ppm accounting for an OH group being part of a hydrogen bridge.
30. +, 161 (16), 149 (10), 143 (23), 132 (27), 111 (32), 98 (100), 84 (67), 55 (71).
31. In a control experiment we could show that diketone 3 did not react further to give the corresponding 1,2,3-trione, even if large excess of sodium nitrite in combination with longer reaction times was used.
32. 2 and 25 mL of concd HCl. The crude product was purified either by filtration over a pad of silica gel (5:1) using hexane-EtOAc (50:1) as eluent or by crystallization from hexane-EtOAc.
33. 3 (241.33): C, 64.70; H, 9.61; N, 5.80. Found: C, 64.83; H, 9.70; N, 5.88.
34. Rüedi, G.; Nagel, M.; Hansen, H.-J. Org. Lett. 2003, 5, 2691.
35. +], 77 (75), 69 (100), 55 (94).
36. Several reactions were conducted on a 20 g scale.