Synthesis of Trisubstituted Imidazoles Using Lewis and Bronsted Acid Catalysts

Year 2012, Volume: 25 Issue: 1, 29 - 34, 24.01.2012

Rahim Hekmatshoar , Rahim Hekmatshoar , Hajar Jahanbakhshı Farnoosh Mousavızadeh Reyhane Rahnamafar

Abstract

An efficient and one-pot method for the preparation of trisubstituted imidazoles by condensation of benzil, different aldehydes and ammonium acetate in the presence of  a catalytic amount of NiSO4.7H2O or H3BO3 under different conditions is reported.

 

 

 

                Key Words: Trisubstituted imidazoles, Multi-component

                                     reactions, NiSO4.7H2O, H3BO3, one-pot

                                    reactions,  solid acid catalysts.

 

Keywords

Trisubstituted imidazoles, Multi-component reactions, NiSO4.7H2O, H3BO3, one-pot reactions, solid acid catalysts.

References

• Zhu, J., Bienayme, Wiley-VCH,
• Weinheim.Germany, Reactions”, (2005)
• Orru, R.V.A., De Greef, M., “Recent advances in solution-phase multicomponent methodology for the synthesis of heterocyclic compounds”, Synthesis, 1471-1499, (2003).
• Dembitsky, V.M., Gloriozova, T.A., Poroikov, V. V., “Novel antitumor agents: Marine sponge alkaloids, their synthetic analogs and derivatives”, Mini-rev. Med. Chem, 5: 319-336, (2005).
• Nagawade, R.R., Shinde, D.B., “Zirconyl chloride- catalyzed multicomponent reaction of naphtoles: An expeditions synthesis of amido alkyl naphtols ”, Acta Chim Sslov, 54: 642-646, (2007).
• Vallee, B.L., Auld, D.S., “Zinc coordination, function, and structure of zinc enzymes and other proteins”, Biochemistry, 29:5647-5659, (1990).
• Liu, J., Zhao, Y., Zhou, Y., Li, L., Zhang, T.Y., Zhang, H.,“ Imidazolylidene carbene ligated palladium catalysis of the Heck reaction in the presence of air”, Org. Biomol. Chem., 1:3227-3231, (2003).
• Grimmett, M.R., Katritzky, A.R. ,Ress, C. W., Scriven, E.F.V., “Comprehensive Heterocyclic Chemistry II” ,Pergamon Press , Oxford(eds), 3: 77-220, (1996).
• Murry, J. A.,“ Synthetic methodology utilized to prepare substituted imidazole P38 MAP kinase inhibitors”, Curr. Opin. Drug Discovery Dev, 6: 945-965, (2003).
• Narayana Murthy, S., Madhav, B., Nageswar, Y.V.D., “DABCO as a mild and efficient catalyst system for the synthesis of highly substituted imidazoles strategy”, Tetrahedron Letters, 51: 5252-5257, (2010). condensation
• Schubert, H., Stodolka, H. J., “Diimidazole.II. Synthesis uberbruckten N,N´-Diimidazolen”, Prakt. Chem., 22: 130-139, (1963). und aromatisch
• Tsuji, J., Sakai, K., Nemoto, H., Nagashima, H., “Iron and copper catalyzed reaction of benzylamine with carbon tetrachloride: Facile formation of 2,4,5- Triphenylimidazoline deravatives.” , J. Mol. Cata.l, 18: 169-176, (1983).
• Frantz, E.D., Morency, L., Soheili, A., Murry, J. A., Grabowski, E. J. J., Tillyer, R.D., “Synthesis of substituted Imidazoles via organocatalysis”, Org. Lett., 6: 843-846, (2004).
• Japp, F.R., Robinson, H.H., “ Constitution des lophins und des amarins”, Ber, 15: 1268-1270, (1882).
• Wasserman, H.H., Long, Y. O., Zhang, R., Parr, J., “Alkenyl tricarbonyl derivatives of α-amino acids as trielectrophiles. substituted productes”, Tetrahedron Lett, 43: 3351- 3353, (2002). of heterocyclic
• Liu, J., Chem, J., Zhao, J., Zhao, Y., Li, L., Zhang, H., “A modified procedure for the synthesis of 1- arylimidazoles”, Synthesis, 2661-2666, (2003).
• Weinmann, H., Harre, M., Koeing, K., Merten, E., Tilestam, U., “Efficient and environmentally friendly Tetrahedron Lett., 43: 593-595, (2002). 2-amino-imidazole”,
• Sarshar, S., Siev, D., Mjalli, A. M. M., “ Imidazole libraries on solid support”, Tetrahedron Lett. , 37, 835-838, (1996).
• Wilson, K., Clark, J.H., “Solid acids and their uses as environmentally friendly catalysts in organic synthesis”, Pure Appl. Chem, 72: 1313-1319, (2000).
• Kidwai, M., Mothsra, P., Bansal, V., Somvanshi, R. K., Ethayathulla, A. S., Dey, S., Singh, T., “One pot synthesis of highly substituted imidazoles using molecular iodine: A versatile catalyst”, J. Mol. Catal. A: Chem, 265: 177-182, (2007).
• Heravi. M. M., Bakhtiari, K.H., Oskooie, H. A., Taheri, S.H., “Synthesis of 2,4,5-triaryl-imidazoles catalyzed by NiCl2.6H2O under heterogeneous system ”, J. Mol. Catal. A: Chem, 263: 279-281, (2007).
• Siddiqui, S.A., Narkhede, U.C., Palimkar, S.S., Daniel, T., Lahoti, R.J., Srinivasan, K.V., “Room temperature ionic liquid promoted improved and rapid synthesis of 2,4,5-triarylimidazoles from aryl aldehydes and 1,2-diketones or α-hydroxyketones”, Tetrahedron, 61: 3539-3546, (2005).
• Shaabani, A., Rahmati, A., “Silica sulfuric acid as an efficient and recoverable catalyst for the synthesis of trisubstituted imidazoles”, J.Mol.Catal.A:Chem., 249: 246-248, (2006).
• Sivakumar, K., Kathivvel, A., Lalitha, A., “ Simple and efficient method for the synthesis of highly substituted imidazoles reagents”, Tetrahedron Letters, 51: 3018-3021,
• zeolite-supported (2010).
• Das, B., Sudhakar, C., Srinivas, Y., “Efficient synthesis of 5-substituted 2,3-Diphenyl and 5- substituted 1-Aryl-2,3-diphenyl imidazoles using polyethylene Glycol”, Synthetic Communications, 40: 2667-2675, (2010).
• Shaabani, A., Maleki, A., Behnam, M., “Tandem oxidation process using Ceric ammonium nitrate : Three –Component synthesis of trisubstituted imidazoles under Aerobic oxidation conditions”, Synthetic Communications, 39: 102-110, (2009).