Synthesis of 2-Substituted 1-Hydroxyhnidazoles through Directed Lithiation

Journal of Organic Chemistry

Volumn 63, Issue 1, 1998, Pages 12-16

  Eriksen, Birgitte Langer ^a   Vedsø, Per ^a   Morel, Sandrine ^a   Begtrup, Mikael ^a  

^a UNIVERSITY OF COPENHAGEN   (Denmark)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0002638055     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo970355+     Document Type: Article

References (46)

1. Lettau, H. Z. Chem. 1970, 10, 211.
2. Grimmett, M. R. Adv. Heterocycl. Chem. 1970, 12, 103.
3. Grimmett, M. R. Adv. Heterocycl. Chem. 1980, 27, 241.
4. Grimmett, M. R. In Comprehensive Heterocyclic Chemistry; Katritzky, A. R., Rees, C. W., Eds.; Pergamon Press: Oxford, 1984; 5, p 457.
5. Volkamer, K.; Baumgaertel, H.; Zimmennann, H. Angew. Chem., Int. Ed. Engl. 1967, 6, 947.
6. Volkamer, K.; Zimmermann, H. W. Chem. Ber. 1969, 102, 4177.
7. Akagane, K.; Allan, F. J.; Allan, G. G.; Friberg, T.; Omuircheartaigh, S.; Thomson, J. B. Bull. Chem. Soc. Jpn. 1969, 42, 3204.
8. Akagane, K.; Allan, G. G.; Chopra, C. S.; Friberg, T.; Mattila, T.; Omuircheartaigh, S.; Thomson, J. B. Suom. Kemistil. B 1972, 45, 223.
9. Akagane, K.; Allan, G. G. Shikizai Kyokaishi 1973, 46, 555.
10. Ertel, H.; Heubach, G. Justus Liebigs Ann. Chem. 1974, 1399.
11. Lettau, H. Z. Chem. 1970, 10, 338.
12. Volodarskii, L. B.; Vityaeva, E. I. Zh. Org. Khim. 1972, 8, 1887.
13. Beger, J. J. Prakt. Chem. 1969, 311, 746.
14. Scheinbaum, M. L.; Dines, M. B. Tetrahedron Lett. 1971, 2205.
15. Lipshutz, B. H.; Morey, M. C. Tetrahedron Lett. 1984, 25, 1319.
16. Lipshutz, B. H.; Huff, B.; Vaccaro, W. Tetrahedron Lett. 1986, 27, 4241.
17. Laus, G.; Stadiweiser, J.; Klötzer, W. Synthesis 1989, 773.
18. Baus, U.; Reuther, W. Eur. Pat. Appl. EP 1991, 420; Chem. Abstr. 1991, 115, 29334.
19. Baus, U.; Reuther, W. Eur. Pat. Appl. EP 1991, 420; Chem. Abstr. 1991, 115, 29334.
20. Begtrup, M.; Vedsø, P. J. Chem. Soc., Perkin Trans. 1 1995, 243.
21. Watson, A. A. J. Org. Chem. 1974, 39, 2911.
22. Watson, A. A. J. Org. Chem. 1977, 42, 1610.
23. Haraden, M. R.; Jennings, L. J.; McKie, C. M. D.; Parkin, A. Synthesis 1990, 893.
24. Yamada, M.; Fukui, T.; Nunami, K. Synthesis 1995, 1365.
25. Bock, V.; Kloetzer, W.; Singewald, N.; Strieder, G. Synthesis 1987, 1058.
26. Hauser, H.; Kloetzer, W.; Krug, V.; Rzehak, J.; Sandrieser, A.; Singewald, N. Sci. Pharm. 1988, 56, 235.
27. Vedsø, P.; Begtrup, M. J. Org. Chem. 1995, 60, 4995.
28. Uhlmann, P.; Felding, J.; Vedso, P.; Begtrup, M. Unpublished work.
29. Jutzi, P.; Sakrib, W. Chem. Ber. 1973, 106, 2815.
30. Carpenter, A. J.; Ngochindo, R. I. J. Chem. Soc., Perkin Trans. 1 1984, 481.
31. Carpenter, A. J.; Chadwick, D. J. Tetrahedron 1986, 42, 2351.
32. Eriksen, B. L.; Vedsø, P.; Begtrup, M. Unpublished work.
33. Towliati, H. Chem. Ber. 1970, 103, 3952.
34. Lettau, H. Z. Chem. 1971, 11, 10.
35. Imbach, J. L.; Jacquier, R.; Romane, A. Bull. Soc. Chim. Fr. 1967, 451.
36. Kirk, K. L. J. Org. Chem. 1978, 43, 4381.
37. Still, W. C.; Kahn, M.; Mitra, A. J. Org. Chem. 1978, 43, 2923.
38. Flynn, A. P. Chem. Br. 1984, 20, 30.
39. Suffert, J. J. Org. Chem. 1989, 54, 509.
40. Burfield, D. R.; Smithers, R. H. J. Org. Chem. 1978, 43, 3966.
41. Imidazole and 3-chloroperbenzoic acid should not be mixed in the dry state because this may lead to a violent reaction.
42. 13C-NMR spectra.
43. Wasylishen, R. E.; Tomlinson, G. Can. J. Biochem. 1977, 55, 579.
44. Begtrup, M.; Elguero, J.; Faure, J.; Camps, P.; Estopa, C.; Ilavsky, D.; Fruchier, A.; Marzin, C.; de Mendoza, J. Magn. Reson. Chem. 1988, 26, 134.
45. All starting material is consumed if the reaction time is increased, but the yield of 4 decreases due to its further reduction to imidazole.
46. Debus, H. Liebigs Ann. Chem. 1858, 107, 199.