A Four Components, One-Pot Synthesis of New Imidazole Molecular Tweezers Based on 2,4,6-Triarylpyridine as Hinge Region

Document Type: Research Article

Authors

1 Department of Chemistry, Mashhad Branch, Islamic Azad University, Mashhad, Iran

2 Department of Chemistry, Mashhad Branch, Islamic Azad University, P.O. Box 91735-413 Mashhad, I.R. IRAN

Abstract

In the present study, some new bis-imidazole derivatives have been prepared through four-components condensation of 2,6-bis (4-aminophenyl)-4-p-tolylpyridine, benzaldehyde derivatives, benzil and ammonium acetate in presence of acetic acid. The present methodology offers several advantages such as good yields, simple procedure, milder conditions and
the possibility of introducing a variety of substituents at different positions of the imidazole and pyridine rings. These new compounds were confirmed by spectral methods 1H NMR, 13C NMR, FT-IR, and elemental. Also, optimized geometries and chemical shifts have been calculated for the ‎synthesized compounds using Density Functional Theory (DFT) method. Their optimized ‎geometries are not planar.‎

Keywords

Main Subjects


[1] Zhu J., Bienayme H., “Multicomponent Reactions”, Wiley-VCH: Weinheim, Germany (2005).

[2] Kim B.Y., Ahn J.B., Lee H.W., Kang S.K., Lee J.H., Shin J.S., Ahn S.K., Hong C.I., Yoon S.S., Synthesis and Biological Activity of Novel Substituted Pyridines and Purines Containing 2,4-Thiazolidinedione, Eur.. J. Med. Chem. 39 (5): 433-447 (2004).

[4] Shalini K., Sharma P.K., Kumar N., Imidazole and Its Biological Activities: A Review, Der Chemica Sinica, 1(3):36-47 (2010).

[5] Chawla A., Sharma A., Sharma A. K.,Review: A Convenient Approach for the Synthesis of Imidazole Derivatives Using Mcrowaves, Der Pharma Chemica, 4 (1):116-140 (2012).

[6] Bhatnagar A., Sharma, P. K., Kumar N., A Review on Imidazoles: Their Chemistry and Pharmacological Potentials, Int. J. Pharm. Tech. Res., 3 (1): 268-282 (2011).

[7] Enyedy I. J., Sakamuri S., Zaman, W. A., Johnson K. M., Wang, S., Pharmacophore-Based Discovery of Substituted Pyridines as Novel Dopamine Transporter Inhibitors, Bioorg. Med. Chem. Lett., 13(3): 513-517 (2003).

[8] Liu W., Chen Z., Zheng C. J., Liu X. K., Wang K., Li F., Dong Y. P., Ou X. M., Zhang X. H., A Novel Nicotinonitrile Derivative as an Excellent Multifunctional Blue Fluorophore for Highly Efficient Hybrid White Organic Light-Emitting Devices, J. Mater. Chem. C, 3 (34): 8817-8823 (2015).

[10] Hisamatsua Y., Aihara H., Diverse Dimerization of Molecular Tweezers with a 2,4,6-triphenyl-1,3,5-triazine Spacer in the Solid State, Chem. Commun., 46 (27): 4902-4904 (2010).

[11] Krebs F.C., Functionalization of the Hinge Region in Receptor Molecules for Explosive Detection, Tetrahedron Lett., 44 (35): 6643-6646 (2003).

[12] Wang Z., Lu P., Chen S., Gao Z., Shen F., Zhang W., Xu Y., Kwok H. S., Ma Y., Phenanthro[9,10-d] Imidazole as a New Building Block for Blue Light Emitting Materials, J. Mater. Chem., 21: 5451-5456 (2011).

[13] Lee C., Yang W., Parr R.G., Development of the Colle-Salvetti Correlation-Energy Formula Into a Functional of the Electron Density, Phys. Rev. B, 37(2): 785-789 (1988).

[14] Ditchfield R., Self-Consistent Perturbation Theory of Diamagnetism, Mol. Phys., 27 (4): 789-807 (1974).

[15] Karabacak M., Sinha L., Prasad O., Bilgili S., Sachan Alok K., Asiri A.M., Atac A., Spectral Investigation and Theoretical Study of Zwitterionic and Neutral Forms of Quinolinic Acid, J. Mol. Struct., 1095: 100-111 (2015).

[16] Beyramabadi S.A., Eshtiagh-Hosseini H., Housaindokht M.R., Shirzadi S., Morsali A., Naseri M.A., Experimental and Theoretical Characterization of N,Nʹ-bis(2,4-dihydroxybenzylidene)-1,2-Diaminobenzene Schiff base and Its Cu(II) Complex, J. Struct. Chem., 54 (6): 1055-1062 (2013).

[18] Beyramabadi S.A., Morsali A., Javan-Khoshkholgh M., Esmaeili A.A., N,N'-dipyridoxyl Schiff Bases: Synthesis, Experimental and Theoretical Characterization, Spectrochim. Acta Part A, 83 (1): 467-471 (2011).

[20] Behmadi H., Naderipour S., Saadati S. M., Barghamadi M., Shaker M., Tavakoli-Hoseini N., Solvent-Free Synthesis of New 2,4,6-Triarylpyridines Catalyzed by a Brønsted Acidic Ionic Liquid as a Green and Reusable Catalyst, J. Heterocyclic Chem