A facile CAN-mediated transformation of acetoacetamides to oxamates

Journal of Organic Chemistry

Volumn 64, Issue 18, 1999, Pages 6898-6900

  Nair, Vijay ^a   Sheeba, V ^a  

^a REGIONAL RESEARCH LABORATORY CSIR   (India)

Author keywords

[No Author keywords available]

Indexed keywords

ACETAMIDE DERIVATIVE; AMMONIUM NITRATE; CERIUM; OXAMIC ACID;

CHEMICAL BOND; CHEMICAL REACTION; CHEMICAL STRUCTURE; NOTE; REACTION ANALYSIS;

EID: 0032887129     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo9904359     Document Type: Note

References (34)

1. Dalko, P. I. Tetrahedron 1995, 51, 7579.
2. Snider, B. B. Chem. Rev. 1996, 96, 339.
3. Melikyan, G. G. Synthesis 1993, 833.
4. Iqbal, J.; Bhatia, B.; Nayyar, N. K. Chem. Rev. 1994, 94, 519.
5. Heiba, E. I.; Dessau, R. M. J. Am. Chem. Soc. 1972, 94, 2888.
6. Baciocchi, E.; Ruzziconi, R. J. Org. Chem. 1986, 51, 1645.
7. Baciocchi, E.; Casu, A.; Ruzziconi, R. Synlett 1990, 679.
8. Nair, V.; Mathew, J.; Prabhakaran, J. Chem. Soc. Rev. 1997, 127.
9. Nair, V.; Mathew, J. J. Chem. Soc., Perkin Trans. 1 1995, 187.
10. Nair, V.; Mathew, J. J. Chem. Soc., Perkin Trans. 1 1995, 1881.
11. Nair, V.; Mathew, J.; Radhakrishnan, K. V. J. Chem. Soc., Perkin Trans. 1 1996, 1487.
12. Nair, V.; Mathew, J.; Kanakamma, P. P.; Panicker, S. B.; Sheeba, V.; Zeena, S.; Eigendorf, G. K. Tetrahedron Lett. 1997, 38, 2191.
13. Linker, T.; Sommermann, T.; Kahlenberg, F. J. Am. Chem. Soc. 1997, 119, 9377.
14. Cho, L. Y.; Romero, J. R. Tetrahedron Lett. 1995, 36, 8757.
15. Nair, V.; Mathew, J.; Nair. L. G. Synth. Commun. 1996, 26, 4531.
16. DuttaGupta, A.; Singh, R.; Singh, V. K. Synlett 1996, 69.
17. Brimble, M. A.; Elliott, R. J. R.; Turner, P. Tetrahedron 1998, 54, 14053.
18. (a) Feringa, B. L.; Butselaar, R. J. Tetrahedron Lett. 1983, 24, 1193.
19. (b) Adam, W.; Catalini, L. H.; Saha-Moller, C. R.; Will, B. Synthesis 1989, 121.
20. (a) Murahashi, S.; Mitsue, Y.; Ike, K. J. Chem. Soc., Chem. Commun. 1987, 125.
21. (b) Fenton, D. M.; Steinwand, P. J. J. Org. Chem. 1974, 39, 701.
22. (c) Tam, W. J. Org. Chem. 1986, 51, 2977.
23. (d) Pri-bar, I.; Alper, H. Can. J. Chem. 1990, 68, 1544.
24. (a) Sokol, P. E. Org. Synth. 1964, 44, 69.
25. (b) Psiorz, M.; Schmid, R. Chem. Ber. 1987, 120, 1825.
26. (a) Stoffel, P. J. J. Org. Chem. 1964, 29, 2794.
27. (b) McDonald, R. N. J. Org. Chem. 1959, 24, 1580.
28. Richardson, A. G.; Pierce, J. S.; Ried, E. E. J. Am. Chem. Soc. 1952, 74, 4011.
29. Neveux, M.; Bruneau, C.; Lecolier, S.; Dixneuf, P. H. Tetrahedron 1993, 49, 2629.
30. Yokoyama, N.; Walker, G. N.; Main, A. J.; Stanton, J. L.; Morrissey, M. M.; Boehm, C.; Engle, A.; Neubert, A. D.; Wasvary, J. M.; Stephan, Z. F.; Steele, R. E. J. Med. Chem. 1995, 38, 695.
31. Kees, K. L.; Musser, J. H.; Chang, J.; Skowronek, M.; Lewis, A. J. J. Med. Chem. 1986, 29, 2329.
32. Dinsmore, C. J.; Bergman, J. M. J. Org. Chem. 1998, 63, 4131.
33. Amine was taken in dry xylene along with 2,2,6-trimethyl-1,3-dioxin-4-one and refluxed at 140°C for 3 h. The reaction mixture was chromatographed on a silica gel column to afford the acetoacetamide in quantitative yield. Wentrup, C.; Heilmayer, W.; Kollenz, G. Synthesis 1994, 1219 and the references therein.
34. Izawa, Y.; Ishiguro, K.; Tomioka, H. Bull. Chem. Soc., Jpn. 1983, 56, 951.