Synthesis of Triphenyl-1H-imidazole Derivatives Using Pectin as a Green Catalyst

Document Type : Research Article


1 Department of Chemistry, Faculty of Science, Sistan and Baluchestan University, Zahedan, I.R. IRAN

2 epartment of Chemistry, Faculty of Science, Sistan and Baluchestan University, Zahedan, I.R. IRAN

3 Faculty of Chemistry, Urmia University, Urmia, I.R. IRAN


A one-pot synthesis of imidazole scaffolds using multi-component reactions as a highly effective methodology is presented. In this three-component reaction with the use of benzyl, aromatic aldehydes, and ammonium acetate in the presence of pectin as a green catalyst, tri-substituted imidazoles in ethanol as a solvent in high yield were prepared. In this reaction, a variety of aromatic aldehydes with electron-withdrawing and electron-donating groups have been used, and the high yields in the final products demonstrate the catalytic performance of pectin in these types of reactions. Some advantages of this method are the use of pectin as a cheap, green, and non-toxic catalyst, as well as the easy separation of products that excludes the use of chromatography for separation, as well as the high purity of the products obtained in this The type of reaction is very important.


Main Subjects

[1] Reed S.M., Hutchison J.E., Green Chemistry in the Organic Teaching Laboratory: An Environmentally Benign Synthesis of Adipic Acid, J. Chem. Edu., 77: 1627-1628 (2000).
[2] Zhu J., Bienaym´e H., “Multicomponent reactions”, John Wiley & Sons, Inc., Weinheim (2005).
[4] Farhadpour F., Hazeri N., Salahi S., Dastoorani P., Doostmohammadi R., Lashkari M., Ghashang M., Maghsoodlou M. T., Maltose as a Green Catalyst for the Synthesis of 3,4,5-Substituted Furan-2(5H) Ones in Water, Iran. J. Catal., 4: 247-251 (2014).
[5] Tanhatan Nasseri A., Thibault J.F., Ralet M.C., Citrus Pectin: Structure and Application in Acid Dairy Drinks, in: "Benkeblia N. & Tennent P. (Editors), Tree and Forestry Science and Biotecnology", Global Science Book, pp 60-70 (2008).
[6] Sheldon R.A., Catalysis: The Key to Waste Minimization, J. Chem. Tech. Biotechnol., 68: 381-388 (1997).
[7] Beli R., Thakur B.T., Singh R.K., Handa A.K., Chemistry and Uses of Pectin — A Review, Critical Reviews in Food Science and Nutrition., 37: 47-73 (1997).
[8] Voragen A.G.J., Coenen G.J., Verhoef R.P., Schols H.A., Pectin, a Versatile Polysaccharide Present in Plant Cell Walls, Struct. Chem., 20: 263-275 (2009).
[9] Dekamin M.G., Peyman S.Z., Karimi A., Javanshir S., Naimi-Jamal M.R., Barikani M., Sodium Alginate: An Efficient Biopolymeric Catalyst for Green Synthesis of 2-amino-4H-pyran Derivatives, Int. J. Bio. Macromol., 87: 172-179 (2016).
[11] Joule J., Mills K., “Heterocyclic Chemistry at a Glance”, Blackwell, Oxford (2007).
[12] Anderson M., Beattie J.F., Breault G.A., Breed J., Byth K.F., Culshaw J.D., Ellston R.P.A., Green S., Minshull C.A., Norman R.A., Pauptit R.A., Stanway J., Thomas A.P., Jewsbury P.J., Imidazo[1,2-a]pyridines: a Potent and Selective Class of Cyclin-Dependent Kinase Inhibitors Identified Through Structure-Based Hybridization, Bioorg. Med. Chem. Lett., 13: 3021-3026 (2003).
[13] Kim O., Jeong Y., Lee L., Hong S.S., Hong S., Design and Synthesis of Imidazopyridine Analogues as Inhibitors of Phosphoinositide 3-Kinase Signaling and Angiogenesis, J. Med. Chem., 54: 2455-2466 (2011).
[14] Marandi G., Saghatforoush L., Mendoza-Meroño R., García-Granda S., Catalyst-Free Synthesis of 3-(alkylamino)-2-arylimidazo[1,2-a]pyridine-8-carboxylic Acids via a Three-Component Condensation, Tetrahedron Lett., 55: 3052-3054 (2014).
[15] Maghsoodlou M.T., Habibi Khorassani S.M., Hazeri N., Heydari R., Marandi G., Nassiri M., The New γ-Spiroiminolactone Synthesis by Reaction between Alkyl or Aryl Isocyanides and 1,10-phenanthroline-5,6-dione in the Presence of Acetylenic Esters, J. Chem. Res., 2006(4): 220-222 (2006).
[16] Maghsoodlou M.T., Habibi Khorassani S.M., Saghatforoush L., Maghfouri F., Marandi G., Kabiri R., Stereoselective Synthesis of Helical Dihydrodipyrrolophenanthroline and Hindrance Hexa Tert-Butyl Carboxylatodipyrrolophenanthroline from Reaction Between 1,10-Phenanthroline and Dialkyl Acetylenedicarboxylates, J. Heterocyclic Chem., 45: 289-293 (2008).
[17] Hazeri N., Marandi G., Maghsoodlou M.T., Habibi Khorassani S.M., Synthesis of 5H-pyrrolo[1,2-c]imidazoles by Intramolecular Wittig reaction, Lett. Org. Chem., 8: 12-15 (2011).
[18] Marandi G., Saghatforoush L., Kabiri R., A High Performance Route for the Synthesis of Dihydropyrrolo[1,2-f]phenanthridine Scaffolds by Using a One-pot Four-component Reaction, J. Heterocyclic Chem., 53: 734-737 (2016).
[20] Maghsoodlou M.T., Rostami Charati F., Habibi Khorassani S.M., Khosroshahrodi M., Makha M., Synthesis of Pyrrole Phosphonate Esters: Emphasis on Pyrrole NH Acids and Dialkylacetylenic Esters Substitution, Iran. J. Chem. Chem. Eng. (IJCCE),27(1): 105-113 (2008).
[21] Maghsoodlou M.T., Heydari R., Mohamadpour F., Lashkari M.,  Fe2O3 as an Environmentally Benign Natural Catalyst for One-Pot and Solvent-Free Synthesis of Spiro-4H-Pyran Derivatives, Iran. J. Chem. Chem. Eng. (IJCCE),36(4): 31-38 (2017).
[22] 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-Triaryl Imidazoles from Aryl Aldehydes and 1,2-Diketones or Α-Hydroxyketone,Tetrahedron, 61: 3539-3546 (2005).
[23] Tapase A., Sangshetti J., Shinde N.D., Shinde D., Microwave Assisted Sulphamic Acid Catalysed One Pot Synthesis of 2, 4, 5 Triaryl-1H-Imidazoles via. Condensation Reaction, Org. Chem. An Indian J., 8: 227-230 (2012).
[25] Chary M.V., Keerthysri N.C., Vupallapati S.V.N., Lingaiah N., Kantevari S., Tetrabutylammonium Bromide (TBAB) in Isopropanol: An Efficient, Novel, Neutral and Recyclable Catalytic System for the Synthesis of 2,4,5-Trisubstituted Imidazoles, Catal. Commun., 9: 2013-2017 (2008).
[27] Liebert T., Hänsch C., Heinze T., Click Chemistry with Polysaccharides, Macromol. Rap. Commun., 27: 208-213 (2006).
[28] Das B., Kashanna J., Kumar R. A., Jangili P., Synthesis Of 2,4,5-Trisubstituted and 1,2,4,5-Tetrasubstituted Imidazoles in Water Using P-Dodecylbenzenesulfonic Acid as Catalyst, Monatsh Chem., 144: 223-226 (2013).