Synthesis of 2-aryl-1H-benzo[d]imidazole derivatives using nano montmorillonite clay as an efficient catalyst

Alikarami, Mohammad; Nikseresht, Ahmad; Amoozadeh, Tayebeh

doi:10.30473/icc.2019.45788.1538

Document Type : Original Research Article

Authors

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

² Department of Chemistry, Payame Noor University, P.O. BOX 19395-4697 Tehran, Iran

https://doi.org/10.30473/icc.2019.45788.1538

Abstract

Benzimidazoles are among the most important nitrogen-containing heterocyclic compounds that have many pharmaceutical applications; including, antitumor, anticancer, anticorrosive, antibacterial, irritant and enzymatic interceptors. In this research, the synthesis of benzimidazoles using o-phenylenediamine and aldehyde derivatives in the presence of the nano montemurillonite in solvent-free and room temperature conditions has been investigated. All products with relatively good yields were identified by spectral and physical methods.

Graphical Abstract

Keywords

Main Subjects

Organic chemistry

References

[1] V. Mittal, In-situ Synthesis of Polymer Nanocomposites. Wily-VCH, 2011, 1906-1907.

[2] D. Mondal, Md. M.R. Mollick, B. Bhowmick, D. Maity, M.K. Bain, D. Rana, A. Mukhopadhyay, K. Dana, D. Chattopadhyay, Prog. Nat. Sci-Mater. Inter., 2013, 23, 579–587.

[3] M. Malko, A. Antosik, A. Wróblewska, Z. Czech, K. Wilpiszewska, P. Miądlicki, B. Michalkiewicz, Pol. J. Chem. Technol., 2017, 19, 50-58.

[4] C. Ibarguren, P.M. Naranjo, C. Stötzel, M.C. Audisio, E. L.Sham, E.M.F. Torres, F.A. Müller, Applied Clay Science, 2014, 90, 88-95.

[5] M. Biswas, S.S. Ray, Recent progress in synthesis and evaluation of polymer-montmorillonite nanocomposites. In New polymerization techniques and synthetic methodologies Springer, Berlin, Heidelberg, 2001, 167-221.

[6] R.M. Barrer, D.M. MacLeod, Trans. Faraday Soc., 1954, 50, 980-989.

[7] T. Huang, R. Wang, L. Shi, X. Lu, Catal. Commun., 2008, 9, 1143–1147.

[8] M. Asif, Chem. Methodol., 2019, inpress.

[9] I. Islam, E.B. Skibo, R.T. Dorr and D.S. Alberts, J. Med. Chem. 1991, 34, 2954-2961.

[10] H. Nakano, T. Inoue, N. Kawasaki, H. Miyataka, H. Matsumoto, T. Taguchi, N. Inagaki, H. Nagai, T. Satoh, Chem. Pharm. Bull. (Tokyo)., 1999, 47, 1573-8.

[11] J. K. Woodward, J. Allergy Clin. Immunol., 1990, 86, 606-12.

[12] H. Nakano. T. Inoue, N. Kawasaki, H. Miyataka, H. Matsumoto. T. Taguchi, N. Inagaki, H. Naagi T. Satoh, Chem. Pharm. Bull., 1999, 47, 1573-1578.

[13] R. Iemura, M. Hori, H. Ohtaka, Chem. Pharm. Bull., 1989, 37, 962-966.

[14] S. Sajjadifar, E. Khosravani, S. Shiri, Int. J. Chemtech. Res., 2013, 5, 1969-1976.

[15] G. Rusu, G. Dănilă, M. Nechifor, Rev. Med. Chir. Soc. Med. Nat. Iasi., 1993, 97, 269-71.

[16] K. Ishihara, T. Ichikawa, Y. Komuro, S. Ohara, K. Hotta, Arzneim.-Forsch./Drug Res. 1994, 44, 827-830.

[17] K. Kubo, Y. Kohara, E. Imamiya, Y. Sugiura, Y. Inada, Y. Furukawa, K. Nishikawa, T. Naka, J. Med. Chem., 1993, 36, 2182-2195.

[18] G. Piazzesi, L. Morano, J.C. Ruegg, Arzneim.-Forsch./Drug Res., 1987, 37, 1141-1143.

[19] P.A.J. Janssen, F.T.N. Allewijn, Arzneim.-Forsch./Drug Res., 1968, 18, 279-282.

[20] A.B. Allouma, K. Bougrinb, M. Soufiaoui, Tetrahedron Lett., 2003, 44, 5935- 5937.

[21] M. Kalhor, A. Mobinikhaledi, J. Jamshidi, Res. Chem. Intermed., 2013, 39, 3127- 3133.

[22] S. Sajjadifar, Z. Arzehgar, A. Ghayuri, J. Chin. Chem. Soc., 2018, 65, 205-211.

[23] M. Kidwai, J. Chem. Sci., 2010, 122, 607-612.

[24] K.R. Kumar, P.V.V. Satyanarayana, B.S. Reddy, Arch. Appl. Sci. Res., 2012, 4, 1517- 1521.

[25] D.B. Nale, B.M. Bhanage, Synlett, 2015, 26, 2831-2834.

[26] A. Fazlinia, M.H. Mosslemin, H. Sadoughi, J. Korean Chem. Soc., 2010, 54, 579- 581.

[27] J.R. Kumar, J. Jawahar, D.P. Pathak, E-J. Chem. 2006, 3, 278- 285.

[28] H. Xiangming, M. Huiqiang, W. Yulu, ARKIVOC(xiii), 2007, 2007, 150-154.

[29] R. Mohammadi, A. Sajjadi, J. Med. Chem. Sci., 2019, 2, 55-58.

[30] K. Bahrami, M.M. Khodaei, I. Kavianinia, Synthesis, 2007, 417-427.

[31] L-H. Du, Y.-G. Wang, Synthesis, 2007, 675-678.

[32] L. Wang, J. Sheng, H. Tian, C. Qian, Syn. Commun., 2004, 34, 4265-4272.

[33] Y. Venkateswarlu, S.R. Kumar, P. Leelavathi, Org. Med. Chem. Lett., 2013, 3, 1-7.

[34] E. Rezaee Nezhad, R. Tahmasebi, Asian J. Green Chem., 2019, 3, 34-42.

[35] P. Shirkhani, H. Seifournia, E. Mirzajanzadeh, M. Rekavandi, M. Sarayloo, S. Afshari Sharif Abad, Z. Malkeshi, S. Rostamian Tuyehdarvary, Asian J. Green Chem., 2018, 2, 160-170.

[36] S. Sajjadifar, S.A. Mirshokraie, N. Javaherneshan, O. Louie, Am. J. Org. Chem., 2012, 2, 1-6.

[37] S. Sajjadifar, I. Amini, H. Jabbari, O. Pouralimardan, M. Fekri, K. Pal, Iran. Chem. Commun., 2019, 7, 191-199.

[38] (a) S. Sajjadifar, Chemical Methodologies, 2017, 1, 1-11; (b) S. Rezayati, S. Sajjadifar, Journal of Sciences, Islamic Republic of Iran, 2014, 25, 329-337; (c) H. Veisi, D. Kordestani, S. Sajjadifar, M. Hamelian, Iran. Chem. Commun., 2014, 2, 27-33; (d) H. Veisi, A. Sedrpoushan, P. Mohammadi, A.R. Faraji, S. Sajjadifar, RSC Advances, 2014, 4, 25898-25903; (e) S. Sajjadifar, M.A. Zolfigol, G. Chehardoli, S. Miri, International Journal of ChemTech Research, 2013, 5, 422-429; (f) ER Nezhad, S. Sajjadifar, Z. Abbasi, S. Rezayati, Journal of Sciences, Islamic Republic of Iran, 2014, 25, 127-134.

[39] (a) E. Rezaee Nezhad, F. Heidarizadeh, S. Sajjadifar, Z. Abbasi, Journal of Petroleum Engineering, 2013, 2013, http://dx.doi.org/10.1155/2013/203036; (b) S. Sajjadifar, International Journal of ChemTech Research, 2013, 5, 385-389; (c) M.A. Zolfigol, H. Vahedi, A. Massoudi, S. Sajjadifar, O. Louie, Clinical Biochemistry, 2011, 13, S219; (d) S. Sajjadifar, H. Vahedi, A. Massoudi, O. Louie, Molecules, 2010, 15, 2491-2498; (e) S. Sajjadifar, O. Louie, Journal of chemistry, 2013, 2013, http://dx.doi.org/10.1155/2013/674946; (f) S. Sajjadifar, G. Mansouri, S. Miraninezhad, Asian J. Nanosci. Mater., 2018, 1, 11-18.

Iranian chemical communication

Synthesis of 2-aryl-1H-benzo[d]imidazole derivatives using nano montmorillonite clay as an efficient catalyst

References

References

Volume 8, Issue 1
January 2020
Pages 42-48

Synthesis of 2-aryl-1H-benzo[d]imidazole derivatives using nano montmorillonite clay as an efficient catalyst

References

References

Volume 8, Issue 1January 2020Pages 42-48

Volume 8, Issue 1
January 2020
Pages 42-48