An Efficient and Green Protocol for The Synthesis Of 2- Arylbenzimidazoles Using Malic Acid as a Homogeneous and Reusable Catalyst

Authors

  • Sandeep B. Kasar  Prof. John Barnabas Post Graduate School for Biological Studies, Department of Chemistry, Ahmednagar College, Ahmednagar, Maharashtra, India.
  • Shankar R. Thopate  Prof. John Barnabas Post Graduate School for Biological Studies, Department of Chemistry, Ahmednagar College, Ahmednagar, Maharashtra, India.

Keywords:

O-Phenylenediamine, Benzimidazole, Aldehyde, Malic Acid.

Abstract

A straightforward convenient and eco-friendly methodology is developed for the synthesis of substituted 2-arylbenzimidazoles by using malic acid as a catalyst in aqueous medium. O-phenylenediamines and aromatic aldehydes condenses together to give benzimidazole derivatives. This methodology uses easily available non-toxic naturally occurring malic acid as a catalyst. The reaction is very simple, convenient and straightforward and gives moderate to high yields of 2-arylbenzimidazoles.

References

  1. Synthetic approaches to benzimidazoles from O-phenylenediamine: A literature review, Shatha Ibrahim Alaqeel, Journal of Saudi Chemical Society, 21 (2017) 229-237 and references therein.
  2. 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, 4 (1992) 395-398.
  3. 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, 5 (2012) 139-145.
  4. R. R. Nagawade and D. B. Shinde, "BF3.OEt2 Promoted Solvent Free Synthesis of Benzimidazole Derivatives," Chinese Chemical Letters, 17 (2006) 453- 456.
  5. 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, 122 (2012) 607-612.
  6. P. Sun and Z. Hu, "The Convenient Synthesis of Benzimidazole Derivatives Catalyzed by I2 in Aqueous Media," Journal of Heterocyclic Chemistry, 43 (2006) 773-775.
  7. 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.
  8. R. Trivedi, S. K. De and R. A. Gibbs, "A Convenient One-Pot Synthesis of 2-Substituted Benzimidazoles," Journal of Molecular Catalysis A: Chemical, 245 (2006) 8-11.
  9. 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 Lett. 50 (2009) 1495-1497.
  10. R. K. Kumar, P. V. V. Satyanarayana and S. B. Reddy, "NaHSO4-SiO2 Promoted Synthesis of Benzimidazole Derivatives," Archives of Applied Science Research, 4 (2012) 1517-1521.
  11. C. Mukhopadhyay and P. K. Tapaswi, "PEG-Mediated Catalyst-Free Expeditious Synthesis of 2-Substituted Benzimidazoles and Bis-Benzimidazoles under Solvent-Less Conditions," Tetrahedron Lett. 49 (2008) 6237-6240.
  12. K. Bahrami, M. M. Khodaei and F. Naali, "H2O2/ Fe(NO3)3-Promoted Synthesis of 2-Arylbenzimidazoles and 2-Arylbenzothiazoles" Synlett, 4 (2009) 569-572.
  13. 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," Synth. Commun, 34 (2004) 4265-4272. 
  14. A. Loupy, A. Petit, J. Hamelin, et al., "New Solvent-Free Organic Synthesis Using Focused Microwaves," Synthesis, 9 (1998) 1213-1234.
  15. 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," Synth. Commun, 32 (2002) 2467-2476.
  16. G. Penieres, I. Bonifas, G. Lopez, et al., "Synthesis of Benzimidazoles in Dry Medium," Synth. Commun, 30 (2000) 2191-2195.
  17. 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 57 (2001) 163-168.
  18. Facile and Efficient Method for Synthesis of Benzimidazole Derivatives Catalyzed by Zinc TriflateRamineni Srinivasulu1, Kannasani Ravi Kumar2, Peruri Veera Venkata Satyanarayana, Green and Sustainable Chemistry, 4 (2014) 33-37.

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International Journal of Scientific Research in Science, Engineering and Technology

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Published

2018-01-22

Issue

Volume 4, Issue 3, January-February-2018

Section

Research Articles

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This work is licensed under a Creative Commons Attribution 4.0 International License.

How to Cite

[1]
Sandeep B. Kasar, Shankar R. Thopate "An Efficient and Green Protocol for The Synthesis Of 2- Arylbenzimidazoles Using Malic Acid as a Homogeneous and Reusable Catalyst" International Journal of Scientific Research in Science, Engineering and Technology (IJSRSET), Print ISSN : 2395-1990, Online ISSN : 2394-4099, Volume 4, Issue 3, pp.50-53, January-February-2018.