Four-component, one-pot synthesis of tetra-substituted imidazoles using a catalytic amount of MCM-41 or p-TsOH

Synthetic Communications

Volumn 40, Issue 9, 2010, Pages 1270-1275

  Shoar, Rahim Hekmat ^a   Rahimzadeh, Golnaz ^a   Derikvand, Fatemeh ^a   Farzaneh, Maryam ^a  

^a ALZAHRA UNIVERSITY   (Iran)

Author keywords

MCM 41; Multicomponent one pot reactions; P TsOH; Tetra substituted imidazoles

Indexed keywords

1 BENZYL 2 (4 METHYLPHENYL) 4,5 DIPHENYLIMIDAZOLE; 1 BENZYL 2,4,5 TRIPHENYLIMIDAZOLE; 2 (4 CHLOROPHENYL) 1,4,5 TRIPHENYLIMIDAZOLE; ALDEHYDE; AMINE; AMMONIUM ACETATE; BENZALDEHYDE; BENZIL; IMIDAZOLE DERIVATIVE; MCM 41; SILICON DIOXIDE; TOLUENESULFONIC ACID DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; CONTROLLED STUDY; ONE POT SYNTHESIS; POLYMERIZATION; STRUCTURE ANALYSIS; SUBSTITUTION REACTION;

EID: 77951087055     PISSN: 00397911     EISSN: 15322432     Source Type: Journal    
DOI: 10.1080/00397910903068204     Document Type: Article

References (18)

1. Frantz, D. E.; Morency, L.; Soheili, A.; Murry, J. A.; Grabowski, E. J. J.; Tillyer, R. D. Synthesis of substituted imidazoles via organocatalysis. Org. Lett. 2004, 6, 843-846. (Pubitemid 38387989)
2. Lee, J. C; Laydon, J. T.; McDonnell, P. C; Gallagher, T. F.; Kumar, S.; Green, D.; McNulty, D.; Blumenthal, M.; Heys, J. R.; Landvatter, S. W.; Strickler, J. E.; McLaughlin, M. M.; Siemens, I. R.; Fisher, S. M.; Livi, G. P.; White, J. R.; Adams, J. L. A protein kinase involved in the regulation of inflammatory cytokine biosynthesis. Nature 1994, 372, 739-746.
3. Stoeck, V.; Schunack, W. N-Substituted imidazoles from aldehydes, 1,2-diketones, primary amines, and liquid ammonia. Arch. Pharmaz. 1974, 307, 922-925.
4. Davidson, D.; Weiss, M.; Jelling, M. The action of ammonia on benzil. J. Org. Chem. 1937, 2, 319-327.
5. Stoeck, V.; Schunack, W. Imidazole syntheses, 8: Weidenhagen synthesis of N-substituted imidazoles. Arch. Pharmaz. 1976, 309, 421-425.
6. Consonni, R.; Croce, P. D.; Ferraccioli, R.; Rosa, C. L. A new approach to imidazole derivatives. J. Chem. Res., Synop. 1991, 7, 188-189.
7. Schubert, H.; Stodolka, H. Diimidazole, 2: Synthese von aliphatisch und aromatisch uberbruckten N,N'-diimidazolen. J. Prakt. Chem. 1963, 22, 130-139.
8. Evans, D. A.; Lundy, K. M. Synthesis of diphthamide, the target of diphtheria-toxin-catalyzed ADP-ribosylation in protein-synthesis elongation factor II. J. Am. Chem. Soc. 1992, 114, 1495-1496.
9. Claiborne, C. F.; Liverton, N. J.; Nguyen, K. T. An efficient synthesis of tetra-substituted imidazoles from N-(2-oxo)-amides. Tetrahedron Lett. 1998, 39, 8939-8942.
10. Balalaie, S.; Arabanian, A. One-pot synthesis of tetra-substituted imidazoles catalyzed by zeolite HY and silica gel under microwave irradiation. Green Chem. 2000, 2, 274-276. (Pubitemid 33205956)
11. Laszlo, P. Preparative Chemistry Using Supported Reagents; Academic Press: San Diego, 1987.
12. 7 n-alkanes over Pt-loaded zirconium containing Al-MCM-41 molecular sieves. Micropor. Mesopor. Mat. 2004, 71, 109-115. (Pubitemid 38728313)
13. Corma, A.; Navarro, M. T.; Pariente, J. P. Synthesis of an ultralarge pore titanium silicate isomorphous to MCM-41 and its application as catalyst for selective oxidation of hydrocarbons. J. Chem. Soc., Chem. Commun. 1994, 147-148.
14. Kloetstra, R. K.; Van Bekkum, H. Base and acid catalysis by the alkali-containing MCM-41 mesoporous molecular sieve. J. Chem. Soc., Chem. Commun. 1995, 1005-1006.
15. Li, T.; Chenga, S.; Lee, J.-F.; Jang, L.-Y. MCM-41-supported Mo=Zr mixed oxides as catalysts in liquid phase condensation of 2-methylfuran with acetone. J. Mol. Catal. A: Chem. 2003, 198, 139.
16. Kidawi, M.; Sexena, S.; Rastogi, S. An efficient synthesis of 2,4,5-trisubstituted and 1,2,4,5-tetrasubstituted-1H-imidazoles. Bull. Korean Chem Soc. 2005, 26, 2051.
17. Kidawi, M.; Mothsra, P.; Bansal, V.; Somvanashi, R. K.; Ethayathulla, A. S.; Dey, S.; Singh, T. P. Synthesis of imidazole derivatives and its antibacterial activity. J. Mol. Catal. A.: Chem. 2007, 265, 177.
18. 2O. J. Mol. Catal. A. Chem. 2007, 263, 112.