Efficient Cyclodesulfurization of N-(2-Hydroxyethyl)-N′-Arylthioureas to Δ2-Oxazolines Using Superoxide Radical Anion

Synlett

Volumn 1997, Issue 11, 1997, Pages 1324-1326

  Kim, Yong Il ^a   Kim, Yong Hae ^a  

^a Korea Advanced Institute of Science and Technology (KAIST)   (South Korea)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0003110946     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1997-1030     Document Type: Article

References (35)

1. Green, T.W. Protective Groups in Organic Synthesis; Wiely:New York, 1991; p 265.
2. Kobsyashi, S.; Saegusa, T. In Ring Opening Polymerization; Ivin, K. J.; Saegusa, T., Eds.; Elsevier: New York, 1981; vol. 2, p761.
3. a) Meyers, A. I.; Shipman, M. J. Org. Chem. 1991, 56, 7098.
4. b) Evans, D. A.; Woerpel, K. A.; Hinmann, M. M.; Faul, M. M. J. Am. Chem. Soc. 1991, 113, 726.
5. c) Lowenthal, R. E.; Masamune, S. Tetrahedron Lett. 1990, 31, 6005.
6. d) Studer A. Synthesis 1996, 793.
7. Bodor, N.; Miller J. H. Drugs of the future; Prous, J.R., Ed.; J.R. Prous: Barcelona, 1981; vol. 6, p 165-182.
8. a) Roush, D. M.; Patel, M. M. Synth. Commun. 1985, 15(8), 675.
9. b) Wenker, H. J. Am. Chem. Soc. 1935, 57, 1079.
10. c) Sund, C.; Ylikaski, J.; Kwiatkowski, M. Synthesis 1987, 853.
11. Feump, J. A. Chem. Rev. 1971, 71, 483. Reference cited therein
12. a) Oda, R.; Ohano, M.; Tokiura, S; Misumi, F. Bull. Chem. Soc. Jpn. 1962, 35, 1219.
13. b) Feinaur, R. Angew. Chem. Int. Ed. Engl. 1966, 5, 894.
14. c) Feinaur, R. Angew. Chem. 1966, 78, 938.
15. a) Lambert, R. F.; Thompson, G.; Kristofferson, C. E. J. Org. Chem. 1964, 29, 3116.
16. b) Fanta, P. E.; Deutsch, A. S. J. Org. Chem. 1958, 23, 72.
17. c) Kashelikar, D. V.; Fanta, P. E. J. Am. Chem. Soc. 1960, 82, 4927.
18. a) Suaud-Chagny, M. F.; Mermet, C.; Tibirica, E.; Bousquet, P.; Gionon, F. J. Pharmacology 1992, 213, 305.
19. b) Hiltmann, R.; Wollweber, H.; Stoepel, K.; Puls, W. U.S. Patent 3598833, Aug. 10, 1971; Chem. Abslr. 1969, 71. 101842x.
20. c) Gluchowski, C. U.S. Patent 5066664, Nov. 19, 1991; Chem. Abstr. 1992, 116, 59357p.
21. Najer, H.; Chabrier, P.; Giudicolli, R. Bull. Soc. Chim. Fr. 1959, 1611; Chem. Abstr. 1960, 54, 9889.
22. Najer, H.; Chabrier, P.; Giudicolli, R. Bull. Soc. Chim. Fr. 1959, 1611; Chem. Abstr. 1960, 54, 9889.
23. Heine, H. W.; Kenyon, W. G.; Johnson, E. M. J. Am. Chem. Soc. 1961, 83, 2570.
24. Heine, H. W.; Kaplan, M. S. J. Org Chem. 1967, 32, 3069.
25. Pfeil, E.; Milzner, K. Angew. Chem. Int. Ed. Engl. 1966, 5, 667.
26. Sawyer, D. T.; Valentine, J. S. Acc. Chem. Res. 1981, 14, 393.
27. Fridovich, I. Acc. Chem. Res. 1982, 15, 200.
28. Sawyer, D. T. ; Gibian, M. J. Tetrahedron 1979, 35, 1471.
29. Kim, Y. H.; Yon, G. H. J. Chem. Soc. Chem. Commum. 1983, 715.
30. Kim, Y. H.; Chang, H. S.; Lim, S. C. Bull. Korean Chem. Soc. 1987, 8, 56.
31. Adcock, B; Lawson, A. J. Chem. Soc. 1965, 474.
32. Lee-Ruff, E. Chem. Soc. Rev. 1977, 6, 195.
33. Moro-Oka, Y.; Foote, C. S. J. Am. Chem. Soc. 1976, 98, 1510.
34. Katrizky, A. R.; Langthorne, R. T.; Patel, R. C.; Lhommet, G. Tetrahedron 1981, 37, 2383.
35. Boyd, R. N.; Rittner, R. C. J. Am. Chem. Soc. 1959, 82, 2032.