An efficient procedure for the preparation of 4-substituted 5-aminoimidazoles

Journal of Organic Chemistry

Volumn 68, Issue 1, 2003, Pages 50-54

  McLaughlin, Mark ^a   Mohareb, Rafat M ^a,b   Rapoport, Henry ^a  

^a UNIVERSITY OF CALIFORNIA   (United States)

^b CAIRO UNIVERSITY   (Egypt)

Author keywords

[No Author keywords available]

Indexed keywords

HETEROCYCLIC COMPOUNDS;

AMINES; CATALYSIS; PHASE TRANSITIONS;

AROMATIC COMPOUNDS;

AMINE; GLYCINE; HETEROCYCLIC COMPOUND; IMIDAZOLE DERIVATIVE; NITRILE;

ALKYLATION; ARTICLE; CATALYSIS; CYCLIZATION; REACTION ANALYSIS; SYNTHESIS;

EID: 0037427984     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo026257s     Document Type: Article

References (34)

1. Lythgoe, D. J.; Ramsden, C. A. Adv. Heterocycl. Chem. 1994, 61, 1, and references therein.
2. Butler, R. N. In Comprehensive Heterocyclic Chemistry; Potts, K. T., Ed.; Pergamon: Oxford, 1984; Vol. 5, p 802.
3. (a) Butler, R. N. Adv. Heterocycl. Chem. 1977, 21, 323.
4. (b) Singh, H.; Chawla, A. S.; Kapoor, V. K.; Paul, D.; Malhotra, R. K. Prog. Med. Chem. 1980, 17, 151.
5. Sjosdedt, G.; Gringas, L. Organic Syntheses; Wiley: New York, 1955; Collect. Vol. III, p 95.
6. Taguchi, H. Tetrahedron Lett. 1973, 24, 1137.
7. Dorn, H.; Zubeck, A. Organic Syntheses; Wiley: New York, 1973; Collect. Vol V, p 39.
8. Katritzski, A. R.; Lagowski, J. M. In Comprehensive Heterocyclic Chemistry; Potts, K. T., Ed.; Pergamon: Oxford, 1984; Vol. 5, p 28.
9. (a) Hunter, G.; Nelson, J. A. Can. J. Res., Sect. B 1941, 19, 296.
10. (b) Farger, R. G.; Pyman, F. L. J. Chem. Soc. 1919, 115, 217.
11. (c) Lawson, A. J. Chem. Soc. 1956, 307.
12. (a) Schrimsher, J. L.; Schendel, F. J.; Stubbe, J. Biochemistry 1986, 25, 4356.
13. (b) Schrimsher, J. L.; Schendel, F. J.; Stubbe, J.; Smith, J. M. Biochemistry 1986, 25, 4366.
14. Estramareix, B.; David, S. Biochem. Biophys. Res. Commun. 1986, 134, 1136.
15. (a) Humphries, M. J.; Ramsden, C. A. Synthesis 1999, 985.
16. (b) Humphries, M. J.; Ramsden, C. A. Synlett 1995, 203. 50-54
17. (a) Peinador, C.; Quintela, J. M.; Moreira, M. J. Tetrahedron 1997, 53, 8269.
18. (b) Corelli, F.; Summa, A. B.; Brogi, A.; Monteagudo, E.; Botta, M. J. Org. Chem. 1995, 60, 2008.
19. (c) Birkett, P. R.; King, H.; Chapleo, C. B.; Ewing D. F.; MacKenzie, G. Tetrahedron 1993, 49, 11029.
20. (d) Agathocleous, D. C.; Shaw, G. J. Chem. Soc., Perkin Trans. 1 1993, 2555.
21. (e) Al-Shaar, A. H.; Gilmour, D. W.; Lythgoe, D. J.; McClenaghan, I.; Ramsden, C. A. J. Chem. Soc., Perkin Trans. 1 1992, 2779.
22. (f) Cristalli, G.; Eleuteri, A.; Franchetti, M.; Vittori, S.; Lupidi, G. J. Med. Chem. 1991, 34, 1187.
23. (g) Mackenzie, G.; Wilson, H. A.; Shaw, G.; Ewing, D. J. Chem. Soc., Perkin Trans. 1 1988, 2541.
24. (h) Kadir, K.; Shaw, G.; Wright, D. J. Chem. Soc., Perkin Trans. 1 1980, 2728.
25. (a) Staudinger, H.; Meyer, J. Helv. Chim. Acta 1919, 2, 635.
26. (b) Vaultier, M.; Knouzi, N.; Carrie, R. Tetrahedron Lett. 1983, 24, 763.
27. Mitsonobu, O. Synthesis 1981, 1.
28. Hofmann, K.; Johl, A.; Furlenmeir, A. E.; Kappeler, H. J. Am. Chem. Soc. 1957, 79, 1636.
29. Sugano, H.; Miyoshie, M. Bull. Chem. Soc. Jpn. 1973, 46, 669.
30. Nollet, A. J. H.; Huting, C. M.; Pandit, U. K. Tetrahedron 1969, 25, 5971.
31. O'Donnell, M. J. Aldrichim. Acta 2001, 34, 3.
32. O'Donnell, M. J.; Polt, R. L. J. Org. Chem. 1982, 47, 2663.
33. O'Donnell, M. J.; Eckrich, T. M. Tetrahedron Lett. 1978, 4625.
34. Watkins, B. E.; Rapoport, H. J. Org. Chem. 1982, 47, 4471.