GSC  Vol.4 No.1 , February 2014
Facile and Efficient Method for Synthesis of Benzimidazole Derivatives Catalyzed by Zinc Triflate
ABSTRACT

We report the synthesis of benzimidazole derivatives using zinc triflate as an efficient catalyst. One-pot synthesis of 2-substituted benzimidazole derivatives from o-phynelyenediamine and substituted aldehydes were developed under zinc triflate in ethanol solvent at reflux temperature.


Cite this paper
R. Srinivasulu, K. Ravi Kumar and P. Veera Venkata Satyanarayana, "Facile and Efficient Method for Synthesis of Benzimidazole Derivatives Catalyzed by Zinc Triflate," Green and Sustainable Chemistry, Vol. 4 No. 1, 2014, pp. 33-37. doi: 10.4236/gsc.2014.41006.
References
[1]   H. Zarrinmayeh, A. M. Nunes, P. L. Ornstein, D. M. Zimmerman, M. B. Arnold, D. A. Schober, S. L. Gackenheimer, R. F. Bruns, P. A. Hipskind, T. C. Britton, B. E. Cantrell and D. R. Gehlert, “Synthesis and Evaluation of a Series of Novel 2-[(4-Chlorophenoxy)methyl]-benzimidazoles as Selective Neuropeptide Y Y1 Receptor Antagonists,” Journal of Medical Chemistry, Vol. 41, No. 15, 1998, pp. 2709-2719.
http://dx.doi.org/10.1021/jm9706630

[2]   Z. Zhu, B. Lippa, J. C. Drach and L. B. Towersend, “Design, Synthesis, and Biological Evaluation of Tricyclic Nucleosides (Dimensional Probes) as Analogues of Certain Antiviral Polyhalogenated Benzimidazole Ribonucleosides,” Journal of Medical Chemistry, Vol. 43, No. 12, 2000, pp. 2430-2437.
http://dx.doi.org/10.1021/jm990290y

[3]   H. A. Barker, R. D. Smyth, H. Weissbach, J. I. Toohey, J. N. Ladd and B. E. Volcani, “Isolation and Properties of Crystalline Cobamide Coenzymes Containing Benzimidazole or 5,6-Dimethylbenzimidazole,” Journal of Biological Chemistry, Vol. 235, No. 2, 1960, pp. 480-488.

[4]   J. C. Sih, W. B. Im, A. Robert, D. R. Graber and D. P. Blackmann, “Studies on (H+-K+)-ATPase Inhibitors of Gastric acid Secretion. Prodrugs of 2-[(2-Pyridinylmethyl) sulfinyl]benzimidazole Proton-Pump Inhibitors,” Journal of Medical Chemistry, Vol. 34, No. 3, 1991, pp. 1049-1062.
http://dx.doi.org/10.1021/jm00107a026

[5]   A. Figge, H. J. Altenbach, D. J. Brauer and P. Tielmann, “Synthesis and Resolution of 2-(2-Diphenylphosphinylnaphthalen-1-yl)-1-isopropyl-1H-benzoimidazole: A New Atropisomeric P,N-Chelating Ligand for Asymmetric Catalysis,” Tetrahedron: Asymmetry, Vol. 13, No. 2, 2002, pp. 137-144.
http://dx.doi.org/10.1016/S0957-4166(02)00079-4

[6]   E. Alcalde, I. Dinares, L. P. Garcia and T. Roca, “An Advantageous Synthesis of 2-Substituted Benzimidazoles Using Polyphosphoric Acid. 2-(Pyridyl)-1H-benzimidazoles, 1-Alkyl-(1H-benzimidazol-2-yl)pyridinium Salts, Their Homologues and Vinylogues,” Synthesis, Vol. 1992, No. 4, 1992, pp. 395-398.
http://dx.doi.org/10.1055/s-1992-26121

[7]   V. S. Padalkar, V. D. Gupta, K. R. Phatangare, V. S. Patil, P. G. Umape and N. Sekar, “Indion-190 Resin: Efficient, Environmentally Friendly and Reusable Catalyst for Synthesis of Benzimidazoles, Benzoxazoles and Benzothiazoles,” Green Chemistry Letters and Reviews, Vol. 5, No. 2, 2012, pp. 139-145.
http://dx.doi.org/10.1080/17518253.2011.585666

[8]   R. R. Nagawade and D. B. Shinde, “BF3.OEt2 Promoted Solvent Free Synthesis of Benzimidazole Derivatives,” Chinese Chemical Letters, Vol. 17, No. 4, 2006, pp. 453-456.

[9]   M. Kidwai, A. Jahan and D. Bhatnagar, “Polyethylene Glycol: A Recyclable Solvent System for the Synthesis of Benzimidazole Derivatives Using CAN as Catalyst,” Journal of Chemical Sciences, Vol. 122, No. 4, 2012, pp. 607-612. http://dx.doi.org/10.1007/s12039-010-0095-7

[10]   P. Sun and Z. Hu, “The Convenient Synthesis of Benzimidazole Derivatives Catalyzed by I2 in Aqueous Media,” Journal of Heterocyclic Chemistry, Vol. 43, No. 3, 2006, pp. 773-775.
http://dx.doi.org/10.1002/jhet.5570430338

[11]   B. Sadeghi and M. G. Nejad, “Silica Sulfuric Acid: An Eco Friendly and Reusable Catalyst for Synthesis of Benzimidazole Derivatives,” Journal of Chemistry, Vol. 2013, 2013, Article ID: 581465.

[12]   R. Trivedi, S. K. De and R. A. Gibbs, “A Convenient One-Pot Synthesis of 2-Substituted Benzimidazoles,” Journal of Molecular Catalysis A: Chemical, Vol. 245, No. 1-2, 2006, pp. 8-11.
http://dx.doi.org/10.1016/j.molcata.2005.09.025

[13]   R. G. Jacob, L. G. Dutra, C. S. Radatz, S. R. Mendes, G. Perin and E. Lenardao, “Synthesis of 1,2-Disubstituted Benzimidazoles Using SiO2/ZnCl2,” Tetrahedron Letters, Vol. 50, No. 13, 2009, pp. 1495-1497.
http://dx.doi.org/10.1016/j.tetlet.2009.01.076

[14]   R. K. Kumar, P. V. V. Satyanarayana and S. B. Reddy, “NaHSO4-SiO2 Promoted Synthesis of Benzimidazole Derivatives,” Archives of Applied Science Research, Vol. 4, No. 3, 2012, pp. 1517-1521.

[15]   C. Mukhopadhyay and P. K. Tapaswi, “PEG-Mediated Catalyst-Free Expeditious Synthesis of 2-Substituted Benzimidazoles and Bis-Benzimidazoles under Solvent-Less Conditions,” Tetrahedron Letters, Vol. 49, No. 43, 2008, pp. 6237-6240.
http://dx.doi.org/10.1016/j.tetlet.2008.08.041

[16]   K. Bahrami, M. M. Khodaei and F. Naali, “H2O2/ Fe(NO3)3-Promoted Synthesis of 2-Arylbenzimidazoles and 2-Arylbenzothiazoles” Synlett, Vol. 2009, No. 4, 2009, pp. 569-572.
http://dx.doi.org/10.1055/s-0028-1087911

[17]   L. Wang, J. Sheng, H. Tian, et al., “An Efficient Procedure for the Synthesis of Benzimidazole Derivatives Using Yb(OTf)3 as Catalyst Under Solvent-Free Conditions,” Synthetic Communications, Vol. 34, No. 23, 2004, pp. 4265-4272. http://dx.doi.org/10.1081/SCC-200039340

[18]   A. Loupy, A. Petit, J. Hamelin, et al., “New Solvent-Free Organic Synthesis Using Focused Microwaves,” Synthesis, Vol. 1998, No. 9, 1998, pp. 1213-1234.
http://dx.doi.org/10.1055/s-1998-6083

[19]   G. V. Reddy, V. V. V. N. S. Ramarao, B. Narsaiah, et al., “A Simple and Efficient Method for the Synthesis of Novel Trifluoromethyl Benzimidazoles under Microwave Irradiation Conditions,” Synthetic Communications, Vol. 32, No. 16, 2002, pp. 2467-2476.
http://dx.doi.org/10.1081/SCC-120003394

[20]   G. Penieres, I. Bonifas, G. Lopez, et al., “Synthesis of Benzimidazoles in Dry Medium,” Synthetic Communications, Vol. 30, No. 12, 2000, pp. 2191-2195.
http://dx.doi.org/10.1080/00397910008087397

[21]   K. Bougrin, A. Loupy, A. Petit, et al., “Nouvelle Voie de Synthèse des 2-Trifluorométhylarylimidazoles sur Montmorillonite K10 en ‘Milieu Sec’ Sous Micro-Onde,” Tetrahedron. Vol. 57, No. 1, 2001, pp. 163-168.
http://dx.doi.org/10.1016/S0040-4020(00)00992-3

[22]   S. R. Kumar, Y. Venkateswarlu and P. Leelavathi, “Synthesis of 1,5-Benzodiazepines Catalyzed by Zinc Triflate in Solvent-Free Medium,” Asian Journal of Chemistry, Vol. 23, No. 4, 2011, pp. 1611-1614.

[23]   X. Zhu and A. Ganesan, “Regioselective Synthesis of 3-Alkylindoles Mediated by Zinc Triflate,” The Journal of Organic Chemistry, Vol. 67, No. 8, 2002, pp. 2705-2708.
http://dx.doi.org/10.1021/jo010996b

[24]   K. C. Lekhok, D. Bhuyan, D. Prajapati and R. C. Boruah, “Zinc Triflate: A Highly Efficient Reusable Catalyst in the Synthesis of Functionalized Quinolines via Friedlander Annulations,” Molecular Diversity, Vol. 14, No. 4, 2010, pp. 841-846.
http://dx.doi.org/10.1007/s11030-009-9214-0

[25]   V. N. Kumar, G. Sridhar, E. Laxminarayana, B. Mallaiah and T. Giri, “Selective Deprotection of t-Butyldimethylsilyl (TBDMS) Ethers Using Zinc (II) Trifluoromethanesulfonate,” Journal of Drug Chemistry (IJPI), Vol. 2, No. 10, 2012, 4p.

[26]   D. Atukuri, R. K. Ravindra and P. K. Pramod, “Zinc Triflate Catalyzed Facile Synthesis of Novel 1,2,4-Trizolinone Derivatives Using 3-Arylsydnone as Synthons,” Letters in Organic Chemistry, Vol. 10, No. 7, 2013, pp. 510-517.
http://dx.doi.org/10.2174/1570178611310070009

[27]   A. J. Blacker, M. M. Farah, M. I. Hall, S. P. Marsden, O. Saidi and J. M. J. Williams, “Synthesis of Benzazoles by Hydrogen-Transfer Catalysis,” Organic Letters, Vol. 11, No. 9, 2009, pp. 2039-2042.
http://dx.doi.org/10.1021/ol900557u

[28]   S. B. Sapakal, K. F. Shelke, S. S. Sonar, B. B. Shingate and M. S. Shingare, “Acidic Ionic Liquid Catalyzed Environmentally Friendly Synthesis of Benzimidazole Derivatives,” Bulletin of the Catalysis Society of India, Vol. 2, 2009, p. 78.

[29]   V. A. Sontakke, S. Ghosh, P. P. Lawande, B. A. Choapade and V. S. Shinde, “A Simple, Efficient Synthesis of 2-Aryl Benzimidazoles Using Silica Supported Periodic Acid Catalyst and Evaluation of Anticancer Activity,” ISRN Organic Chemistry, Vol. 2013, 2013, Article ID: 453682.

[30]   J. Peng, M. Ye, C. Zong, F. Hu, L. Feng, X. Wang and C. Chen, “Copper-Catalyzed Intramolecular C-N Bond Formation: A Straightforward Synthesis of Benzimidazole Derivatives in Water,” The Journal of Organic Chemistry, Vol. 76, No. 2, pp. 716-719.
http://dx.doi.org/10.1021/jo1021426

 
 
Top