Document Type: Original Research Article

Authors

1 Department of Chemistry, Payame Noor University, PO box 19395-3197, Tehran, Iran

2 Department of Chemistry, Ayatollah Alozma Borujerdi University, Borujerd, Iran

3 Department of Nanotechnology, Bharath University,BIHER Research Park, Chennai, Tamil Nadu 600073, India

10.33945/SAMI/ECC.2019.2.7

Abstract

1-Methyl-3-(2-oxyethyl)-1H-Imidazol-3-ium-Borate Sulfonic Acid ([MOEI]-BSA) was easily prepared and used as a new and highly efficient solid acid catalyst for the synthesis of benzimidazole derivatives with high isolated yields. Various substituted benzimidazoles were synthesized by a combination of o-phenylenediamines and aldehydes in the presence of [MOEI]-BSA with excellent yields in water and under a mild and green reaction conditions. This method is also applicable for precursors such as aromatic and unsaturated aldehydes and o-phenylenediamines. Addition of organic part to BSA and synthesis of [MOEI]-BSA as a new Bronsted acidic ionic liquid (BAIL) improved the efficiency of this catalyst. 
1-Methyl-3-(2-oxyethyl)-1H-Imidazol-3-ium-Borate Sulfonic Acid ([MOEI]-BSA) was easily prepared and used as a new and highly efficient solid acid catalyst for the synthesis of benzimidazole derivatives with high isolated yields. Various substituted benzimidazoles were synthesized by a combination of o-phenylenediamines and aldehydes in the presence of [MOEI]-BSA with excellent yields in water and under a mild and green reaction conditions. This method is also applicable for precursors such as aromatic and unsaturated aldehydes and o-phenylenediamines. Addition of organic part to BSA and synthesis of [MOEI]-BSA as a new Bronsted acidic ionic liquid (BAIL) improved the efficiency of this catalyst.

Graphical Abstract

Keywords

[1] A.A. Spasov, I.N. Yozhitsa, I.I. Bugaeva, V. A.Anisimova, Pharmaceutical Chemistry Journal, 1999, 33, 232-243.
 
[2] A.R. Porcari, R.V. Devivar, L.S. Kucera, J.C. Drach, L.B. Townsend, Journal of Medicinal Chemistry, 1998, 41, 1252–1262.
 
[3] M.T. Migawa, J.L. Girardet, J.A. Walker, G.W. Koszalka, S.D. Chamberlain, J.C. Drach, L.B. Townsend, Journal of Medicinal Chemistry, 1998, 41, 1242–1251.
 
[4] I. Tamm, P.B. Sehgal, Advances in Virus Research, 1978, 22, 187 –258.
 
[5] I. Tamm, Science, 1957, 126, 1235-1236.
 
[6] J.S. Kim, B. Gatto, C. Yu, A. Liu, L.F. Liu, E. Lavioe, Journal of Medicinal Chemistry, 1996, 39, 992–998.
 
[7] H. Zarrinmayeh, D.M. Zimmerman, B.E. Cantrell, D.A. Schober, R.F. Bruns, Bioorganic & Medicinal Chemistry Letters, 1999, 9, 647-652.
 
[8] Y. Kohara, K. Kubo, E. Imamiya, T. Wada, Y. Inada, T. Naka, Journal of Medicinal Chemistry, 1996, 39, 5228–5235.
 
[9] W.A. Denny, G.W. Rewcastle, B.C. Bagley, Journal of Medicinal Chemistry, 1990, 33, 814–819.
 
[10] H.M. Elokdah, S.Y. Chai, T.S. Sulkowski, US Patent, 1998, 5, 764, 473.
 
[11] J. Mann, A. Baron, Y. Opoku-Boahen, E. Johansoon, G. Parkmson, L.R. Kelland, S. Neidle, Journal of Medicinal Chemistry, 2001, 44, 138–144.
 
[12] Q. Sun, B. Yan, Bioorganic & Medicinal Chemistry Letters, 1998, 8, 361-364.
 
[13] T. Hisano, M. Ichikawa, K. Tsumoto, M. Tasaki, Chemical and Pharmaceutical Bulletin, 1982, 30, 2996 -3004.
 
[14] R.R. Tidwell, J.D. Geratz, O. Dann, G. Volz, D. Zeh, H. Loewe, Journal of Medicinal Chemistry, 1978, 21, 613–623.
 
[15] P.N. Preston, Benzimidazoles and Congeneric Tricyclic Compounds, In The Chemistry of Heterocyclic Compounds, Part 1, Eds.: Weissberger, A. Taylor, E.C., Wiley: New York, 1981, 6-60.
 
[16] A. Rao, A. Chimirri, S. Ferro, A.M. Monforte, P. Monforte, M. Zappalà, Arkivoc, 2004, v, 147-155.
 
[17] J.G. Smith, I. Ho, Tetrahedron Letters, 1971, 12, 3541-3544.
 
[18] R. Weidenhagen, Chemische Berichte, 1936, 69, 2263 –2272.
 
[19] P. Shirkhani, H. Seifournia, E. Mirzajanzadeh, M. Rekavandi, S. Afshari Sharif Abad, M. Sarayloo, Z. Malkeshi, S. Rostamian Tuyehdarvary, Asian J. Green Chem., 2018, 3, 160-170. DOI: 10.22631/ajgc.2018.112963.1045     
[20] P. Jakobson, M. Jannicke, F. Meyer, Chemische Berichte, 1896, 29, 2682.
 
[21] F.F. Stevens, J.D. Bower, Journal of the Chemical Society, 1949, 2971-2972.
 
[22] S. Sajjadifar, S.A. Mirshokraie, N. Javaherneshan, O. Louie, American Journal of Organic Chemistry, 2012, 2, 1-6.
[23] S. Sajjadifar, O. Louie, Journal of Chemistry, 2013 (2013), pages 6.  http://dx.doi.org/10.1155/2013/674946
[24] S. Sajjadifar, International Journal of ChemTech Research, 2013, 5, 385-389.
[25] S. Sajjadifar, S. Rezayati, International Journal of ChemTech Research, 2013, 1964-1968.
[26] E. Rezaee Nezhad, S. Sajjadifar, S. Miri, S. Karimian, Z. Abbasi, Iranian Journal of Catalyst, 2013, 3, 191-196.
[27] S. Sajjdifar, M. Fedaeian, M. Bakhtiari, S. Rezayati, Chemical Science Transactions, 2014, 3, 107-116. DOI:10.7598/cst2014.637
[28] S. Sajjadifar, M. Norollahi, S. Miri, Iranian Journal of Catalysis, 2014, 4, 55-61.
[29] S. Sajjadifar, S. Rezayati, Chemical Papers, 2014, 68, 531-539.
[30] M. Soheilizad, M. Adib, S. Sajjadifar, Monatshefte fur Chemie-Chemical Monthly, 2014, 145, 1353-1356.
[31] S. Rezayati, S. Sajjadifar, Journal of Sciences, Islamic Republic of Iran, 2014, 25, 329-337.  
[32] S. Sajjadifar, Chem. Method., 2018, 1, 1-11. http://chemmethod.com/article_49740.html, DOI: 10.22631/chemm.2017.88920.1000
[33] S. Sajjadifar, Gh. Mansouri, S. Miraninezhad, Asian J. Nano. Mat., 2018, 1, 9-15. http://www.ajnanomat.com/article_58120.html 
[34] E. Rezaee Nezhad, S. Sajjadifar, Z. Abbasi, S. Rezayati, Journal of Sciences, Islamic Republic of Iran, 2014, 25, 127-134.
[35] H. Veisi, A. Sedrpoushan, P. Mohammadi, A.R. Faraji, S Sajjadifar, RSC Advances, 2014, 4, 25898-25903.