Regio-controlled synthesis of N-substituted imidazoles

Tetrahedron Letters

Volumn 46, Issue 43, 2005, Pages 7315-7319

  Xi, Ning ^a   Xu, Shimin ^a   Cheng, Yuan ^a   Tasker, Andrew S ^a   Hungate, Randall W ^a   Reider, Paul J ^a  

^a AMGEN INC   (United States)

Author keywords

Amino acids; Cyclic thioureas; Imidazoles; Regio controlled synthesis

Indexed keywords

ALPHA AMINO ACID; CARBONYL DERIVATIVE; IMIDAZOLE DERIVATIVE; ISOTHIOCYANIC ACID; THIOUREA DERIVATIVE;

ARTICLE; DESULFURIZATION; DRUG SYNTHESIS; OXIDATION; SUBSTITUTION REACTION;

EID: 25444501550     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2005.08.138     Document Type: Article

References (22)

1. 3 Receptor)
2. M.S. Grimmett A.R. Katritzky C.W. Rees E.F.V. Scriven Comprehensive Heterocyclic Chemistry II Vol. 3 1996 Elsevier Science Oxford 185 211
3. M.S. Grimmett A.R. Katritzky C.W. Rees E.F.V. Scriven Comprehensive Heterocyclic Chemistry II Vol. 3 1996 Elsevier Science Oxford 108 116
4. B. Sezen, and D. Samers J. Am. Chem. Soc. 125 2003 5274 5275
5. J.P. Collman, and M. Zhong Org. Lett. 2 2000 1233 1236
6. J.A. Joule, K. Mills, and G.F. Smith Heterocyclic Chemistry 3rd ed. 1995 Chapman & Hall London pp 372-373
7. W. Marckwald Chem. Ber. 25 1892 2354
8. J.A. Hartley, A. Hazrati, L.R. Kelland, R. Khanim, M. Shipman, F. Suzenet, and L.F. Walker Angew. Chem., Int. Ed. 39 2000 3467 3470
9. S. Husbands, C.A. Suckling, and C.J. Suckling Tetrahedron 50 1994 9729 9742
10. A. Dondoni, and D. Perrone Synthesis 11 1993 1162 1176
11. B. Lygo Synlett 10 1992 793 795
12. K. Satoh, A. Imura, A. Miyadera, K. Kanai, and Y. Yukimoto Chem. Pharm. Bull. 46 1998 587 590
13. For the formation of acyclic thioureas, see: G.A. Winterfeld, A.I. Khodair, and R.R. Schmidt Eur. J. Org. Chem. 2003 1009
14. 2O/MeOH condition was also successfully used for the cyclization, see: J. Fuentes, M.A. Pradera, and I. Robina Tetrahedron 47 1991 5797
15. J. Fuentes, W. Moreda, C. Ortiz, I. Robina, and C. Welsh Tetrahedron 48 1992 6413
16. S. Grivas, and E. Ronne Acta Chem. Scand. 49 1995 225
17. D.W. Karkhanis, and L. Field Phosphorus, Sulfur Silicon Relat. Elem. 22 1985 49
18. G. Frachey, C. Crestini, R. Bernini, R. Saladino, and E. Mincione Heterocycles 38 1994 2621
19. J.M. Dener, L.-H. Zhang, and H. Rapoport J. Org. Chem. 58 1993 1159
20. J.F. O'Connell, J. Parquette, W.E. Yelle, W. Wang, and H. Rapoport Synthesis 1988 767
21. For reviews, see: L.I. Belen'kii L.I. Belen'kii Chemistry of Organosulfur Compounds: General Problems 1990 Ellis Horwood Chichester Chapter 9
22. +.