A Modified Procedure for the Synthesis of 1-Arylimidazoles

Synthesis

Volumn , Issue 17, 2003, Pages 2661-2666

  Liu, Jingping ^a   Chen, Jingbo ^a   Zhao, Jingfeng ^a   Zhao, Yuanhong ^a   Li, Liang ^a   Zhang, Hongbin ^a  

^a YUNNAN UNIVERSITY   (China)

Author keywords

1 arylimidazoles; 1 substituted imidazole; Glyoxal

Indexed keywords

SUBSTITUTION REACTIONS; SYNTHESIS (CHEMICAL);

STERICAL HINDERANCE;

AROMATIC COMPOUNDS;

1 (4 ACETYLPHENYL) 1H IMIDAZOLE; 1 (4 METHOXYPHENYL) 1H IMIDAZOLE; IMIDAZOLE DERIVATIVE; POLYCYCLIC AROMATIC HYDROCARBON DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; DRUG SYNTHESIS; GAS CHROMATOGRAPHY; MASS SPECTROMETRY; PROTON NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS; STEREOSPECIFICITY;

EID: 0346121670     PISSN: 00397881     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2003-42444     Document Type: Article

References (40)

1. (a) Faulkner, D. J. Nat. Prod. Rep. 2000, 17, 1.
2. (b) For reviews, see: Lewis, J. R. Nat. Prod. Rep. 2002, 19, 223.
3. (c) See also: Jin, Z.; Li, Z.; Huang, R. Nat. Prod. Rep. 2002, 19, 454.
4. (d) See also: Ho, J. Z.; Mohareb, R. M.; Ahn, J. H.; Sim, T. B.; Rapoport, H. J. Org. Chem. 2003, 68, 109.
5. I b i d. (2)
6. (a) Maier, T.; Schmierer, R.; Bauer, K.; Bieringer, H.; Buerstell, H.; Sachse, B. German Patent 3217094, 1983; Chem. Abstr. 1984, 100, 85699.
7. ( b) Maier, T.; Schmierer, R.; Bauer, K.; Bieringer, H.; Buerstell, H.; Sachse, B. Canadian Patent 1201716, 1986; Chem. Abstr. 1986, 105, 148200.
8. (c) Maier, T.; Schmierer, R.; Bauer, K.; Bieringer, H.; Buerstell, H.; Sachse, B. US Patent 4820335, 1989; Chem. Abstr. 1989, 111, 19494.
9. Schmierer, R.; Mildenberger, H.; Buerstell, H. German Patent 3614364, 1987; Chem. Abstr. 1988, 108, 37838.
10. (a) Heeres, J.; Backx, L. J. J.; Mostmans, J. H.; Van Cutsem, J. J. Med. Chem. 1979, 22, 1003.
11. (b) Dyer, R. L.; Ellames, G. J.; Hamill, B. J.; Manley, P. W.; Pope, A. M. S. J. Med. Chem. 1983, 26, 442.
12. (c) Lo, Y. S.; Nolan, J. C.; Maren, T. H.; Welstead, W. J. Jr.; Gripshover, D. F.; Shamblee, D. A. J. Med. Chem. 1992, 35, 4790.
13. (d) For a review, see: Lednicer, D. Drugs Based on Five-Membered Heterocycles In Strategies for Organic Drug Synthesis and Design; Wiley: New York, 1998, Chap. 8, 185-241.
14. (e) Adams, J. L.; Boehm, J. C.; Gallagher, T. F.; Kassis, S.; Webb, E. F.; Hall, R.; Sorenson, M.; Garigipati, R.; Griswold, D. E.; Lee, J. C. Bioorg. Med. Chem. Lett. 2001, 11, 2867.
15. For reviews, see (a) Welton, T. Chem. Rev. 1999, 99, 2071.
16. (b) Earle, M. J.; Seddon, K. R. Pure Appl. Chem. 2000, 72, 1391.
17. (c) Sheldon, R. Chem. Commun. 2001, 2399.
18. (d) Bao, W.; Wang, Z.; Li, Y. J. Org. Chem. 2003, 68, 591.
19. (a) Herrmann, W. A.; Köcher, C. Angew. Chem., Int. Ed. Engl. 1997, 36, 2162.
20. (b) McGuinness, D. S.; Green, M. J.; Cavell, K. J.; Skelton, B. W.; White, A. H. J. Organomet. Chem. 1998, 565, 165.
21. (c) McGuinness, D. S.; Cavell, K. J.; Skelton, B. W.; White, A. H. Organometallics 1999, 18, 1596.
22. (d) Zhang, C.; Huang, J.; Trudell, M. L.; Nolan, S. P. J. Org. Chem. 1999, 64, 3804.
23. (e) Bourissou, D.; Guerret, O.; Gabbaï, F. P.; Bertrand, G. Chem. Rev. 2000, 100, 39.
24. (f) Huang, J.; Stevens, E. D.; Nolan, S. P. Organometallics 2000, 19, 1194.
25. (g) Fürstner, A.; Thiel, O. R.; Ackermann, L.; Schanz, H.-J.; Nolan, S. P. J. Org, Chem. 2000, 65, 2204.
26. (h) Stauffer, S. R.; Lee, S.; Stambuli, J. P.; Hauck, S. I.; Hartwig, J. F. Org. Lett. 2000, 2, 1423.
27. (i) Cheng, J.; Trudell, M. L. Org, Lett. 2001, 3, 1371.
28. (j) Fürstner, A.; Leitner, A. Synlett 2001, 290.
29. (k) Lee, S.; Hartwig, J. F. J. Org. Chem. 2001, 66, 3402.
30. (l) Yang, C.; Lee, H. M.; Nolan, S. P. Org. Lett. 2001, 3, 1511.
31. (m) Zhang, T. Y.; Zhang, H. Tetrahedron Lett. 2002, 43, 193.
32. (n) Herrmann, W. A. Angew. Chem., Int. Ed. 2002, 41, 1290.
33. (o) Zhao, Y.; Zhou, Y.; Ma, D.; Liu, J.; Li, L.; Zhang, T. Y.; Zhang, H. Org. Biomol. Chem. 2003, 1, 1643.
34. (a) Gridnev, A. A.; Mihaltseva, I. M. Synth. Commun. 1994, 24, 1547.
35. (b) Gardiner, M. G.; Herrmann, W. A.; Reisinger, C.-P.; Schwarz, J.; Spiegler, M. J. Organomet. Chem. 1999, 572, 239.
36. (c) Kiyomori, A.; Marcoux, J.-F.; Buchwald, S. L. Tetrahedron Lett. 1999, 40, 2657.
37. Hofmann, K. The Chemistry of Heterocyclic Compounds: Imidazole and Its Derivatives; Wiley Interscience: New York; 1956; Part 1, 33.
38. (a) Aldrich Handbook of Fine Chemicals and Laboratory Equipment 2003-2004; Aldrich: Milwaukee, 2003, 1060.
39. (b) Aldrich Handbook of Fine Chemicals and Laboratory Equipment 2003-2004; Aldrich: Milwaukee, 2003, 1250.
40. (c) Aldrich Handbook of Fine Chemicals and Laboratory Equipment 2003-2004; Aldrich: Milwaukee, 2003, 1356.