Four-Component, One-Pot Synthesis of Novel Conjugated Indole-Imidazole Derivatives

Document Type : Research Article


1 Institute of Chemistry, University of the Punjab, Quaid-e-Azam Campus, Lahore, PAKISTAN

2 Govt. Post Graduate Islamia College for Women Cooper Road, Lahore, PAKISTAN

3 Kinnaird College for Women University, Lahore, PAKISTAN

4 Department of Chemistry, The Islamia University of Bahawalpur, Bahawalpur – 63100, PAKISTAN


A series of new tetrasubstituted imidazoles 2-phenyl-3-(1, 4, 5-triphenyl-1H-imidazol-2-yl)-1H-indole derivatives substituted with –F, Cl, Br, I,-OCH3 and -NHCOCH3 were synthesized using a multicomponent reaction. The compounds were obtained in good yields by easy workup and with high purity


Main Subjects

[1] Patela A., Baria S., Talelea G., Patela J., Sarangapani M., Synthesis and Antimicrobial Activity of Some New Isatin Derivatives. Iran J Pharm Res, 4: 249-254 (2006).
[2] Bashir M., Bano A., Ijaz A.S, Chaudhary B.A., Review Recent Developments and Biological Activities of N-Substituted Carbazole Derivatives. Molecules, 20: 13496-13517 (2015).
[3] Guerra A.S.H.S., Diana J.N.M., Laranjeira L.P.M., Maia M.B.S., Colaço .N.C., Lima C.A. Galdino S.L., Pitta I.R., Silva T.G., Anti-Inflammatory and Antinociceptive Activities of Indole–Imidazolidine Derivatives, Int. J. Immunopharmaco, 11: 1816-1822 (2011)
[4] Huesca M., Al-Qawasm R., Young A.H., Lee Y., Aryl Imidazoles and Their use as Anti-Cancer Agents,
US Patent 2008/0262015 A9 (2007).
[6] Na Y.M., Le Borgne M., Pagniez F., Le Baut G., Le Pape P., Synthesis and Antifungal Activity of New 1-halogenobenzyl-3-imidozolylmethylindole Derivatives, Eur J Med Chem, 38: 75-87 (2003).
[7] Kumar N., Sharma P.K., Garg V.K., Singh P., Synthesis and Anticonvulsant Activity of Novel Substituted Phenyl Indoloimidazole Derivatives, Curr. Res. Chem., 3(2): 114-120 (2011).
[8] Hary U., Roettig U., Michael Paul M., Efficient Synthesis of 3-(4,5-dihydro-1H-imidazole-2-yl) -1H-indoles, Tetrahedron Lett.42: 5187–5189 (2001).
[9] Moodya C.J., Jonathan R.A., Roffeya J.A.R., Synthesis of N-protected Nortopsentins B., D. Arkivoc, (iii), 393-401 (2000).
[10] Marchand P., Borgne M.L., Palzer M., Baut G.L., Hartmann R,W., Preparation and Pharmacological Profile of 7-(α-Azolylbenzyl) -1H-indoles and Indolines as New Aromatase Inhibitors, Bioorg. Med. Chem .Lett., 13: 1553-1555 (2003).
[11] Berlinck R.G.S., Britton R., Piers E., Lim L., Roberge M., Rocha R.M., Andersen R.J., Granulatimide and Isogranulatimide, Aromatic Alkaloids with G2 Checkpoint Inhibition Activity Isolated from the Brazilian Ascidian Didemnum granulatum:  Structure Elucidation and Synthesis, J. Org. Chem., 63: 9850-9856 (1998).
[12] Jagar J.J., Smith V.J., 1-[(1-Methyl-1H-imidazol-5-yl)methyl] -1H-indole -5-carbonitrile,Acta Crystatallogr., E68: 03486(2012).
[13] Sisko J., Kassick A.J., Mellinger M., Filan,J.J., Allen A., Olsen M.A.,An Investigation of Imidazole and Oxazole Syntheses Using Aryl-Substituted TosMIC Reagents. J. Org. Chem., 65(5): 1516–1524(2000).
[14] Biraddar J.S., Somappa S.B., Mugali P.S., One-Pot, Solvent-Free Synthesis of 2,5-Disubstituted Indolylimidazoles by Microwave Irradiation, Der Pharma Chemica, 4(1): 437-441 (2012).
[16] Shaterian H.R., Ranjbar M., Azizi K., Efficient Multi-Component Synthesis of Highly Substituted Imidazoles Utilizing P2O5/SiO2 as a Reusable Catalyst, Chinese. J. Chem., 29: 1635-1645 (2011).
[17] Naureen S., S. Noreen S., Nazeer A., Ashraf M., Alam U., Munawar M.A., Khan M.A., Triarylimidazoles- Synthesis of 3-(4,5-diaryl-1H-imidazol-2-yl)-2-phenyl-1H-indole Derivatives as Potent a-Glucosidase Inhibitors, Med. Chem. Res., 24(4): 1584e1595 (2015).
[18] Naureen S., Chaudhry F., Asif N., Munawar M.A., Ashraf M., Nasim F.H., Arshad H., Khan M.A., Discovery of Indole-Based Tetraarylimidazoles as Potent Inhibitors of Urease with Low Antilipoxygenase Activity, Eur. J. Med. Chem., 102: 464e470 (2015).
[19] Robinson B., The Fischer Indole Synthesis,  Chem. Rev., 63: 373-401 (1963).
[20] JonesG.,Stanforth S.P., The Vilsmeier Reaction of Non-Aromatic Compounds, Organic Reactions, 355-686 (2004).