Antitumor Activity and Synthesis of 1, 2-Disubstituted Benzimidazoles in One-Pot Diverse Using Bismuth (III) Trifluoromethanesulfonate as Catalyst

Authors

  • A Venkateswarlu Department of Chemistry, Vikrama Simhapuri University, Nellore-524320, A.P., India.
  • M Harikrishna Department of Chemistry, Vikrama Simhapuri University, Nellore-524320, A.P., India.
  • P. Thriveni Department of Chemistry, Vikrama Simhapuri University, Nellore-524320, A.P., India.

DOI:

https://doi.org/10.22270/ajprd.v12i1.1358

Abstract

Various 1,2-disubstituted benzimidazoles were synthesized in a facile method using Bismuth(III) trifluoromethanesulfonate. It is suggested that formation of an intermediate between the substrate, amine and solvent gives the N-arylation process. This developed protocol is demonstrated by the efficient reactions involving various substituents ranging from electron-withdrawing groups to electron-donating groups.

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Author Biographies

A Venkateswarlu, Department of Chemistry, Vikrama Simhapuri University, Nellore-524320, A.P., India.

Department of Chemistry, Vikrama Simhapuri University, Nellore-524320, A.P., India.

M Harikrishna, Department of Chemistry, Vikrama Simhapuri University, Nellore-524320, A.P., India.

Department of Chemistry, Vikrama Simhapuri University, Nellore-524320, A.P., India.

P. Thriveni, Department of Chemistry, Vikrama Simhapuri University, Nellore-524320, A.P., India.

Department of Chemistry, Vikrama Simhapuri University, Nellore-524320, A.P., India.

References

T. Ishida, T. Suzuki, S. Hirashima, K. Mizutani, A. Yoshida, I. Ando, S. Ikeda, T. Adachi, H. Hashimoto, Bioorg. Med. Chem. Lett. 2006; 16:1859.

J. L. FalcH, M. PiquI, M. GonzJ, I. Buira, E. MIndez, J. Terencio, C. PIrez, M. PrLncep, A. Palomer, A. Guglietta, Eur. J. Med. Chem. 2006; 41:985.

For a review, see: A. J. Battershill, L. J. Scott, Drugs 2006; 66:51.

K. R. Hornberger, G. M. Adjabeng, H. D. Dickson, R. G. Davis-Ward, Tetrahedron Lett. 2006; 47, 5359; b) D. Yang, D.Fokas, J. Li, L. Yu, C. M. Baldino, Synthesis 2005, 47; c) Z.Wu, P. Rea, G. Wickham, Tetrahedron Lett. 2000; 41:9871.

G. D. Maynard, L. D. Bratton, J. M. Kane, T. P. Burkholder, B. Santiago, K. T. Stewart, E. M. Kudlacz, S. A. Shatzer, R. W. Knippenberg, A. M. Farrell, D. E. Logan, Bioorg. Med. Chem. Lett. 1997, 7, 2819; b) U. J. Ries, G. Mihm, B. Narr, K. M. Hasselbach, H. Wittneben, M. Entzeroth, J. C. A. M. Meel, W. Wienen, N. H. Hanel, J. Med. Chem. 1993; 36:4040.

H. Zarinmayeh, A. M. Numes, P. L. Ornstein, D. M. Zimmerman, M. B. Anold, D. A. Schober, J. Med. Chem.1998; 41:2709.

M. Hasegawa, N. Nishigaki, Y. Washio, K. Kano, P. A. Harris, H. Sato. J. Med. Chem. 2007; 50: 4453-70.

J. Falco, M. Pique, M. Ganzalez, I. Baira, E. Mendez, J. Texncio. Eur. J. Med. Chem. 2006; 41: 985-90.

A. Gangjee, A. Vasudevan, S. F. Queener. J. Med. Chem. 1997; 40:479-85.

A. O. H. El-Nezhawy, H. I. El-Diwani, R. R. Schmidt. Eur. J. Org. Chem. 2002; 4137-42.

R. Dua, S. K. Sonwane, S. K. Srivastava and S. D. Srivastava J. Chem. Pharm. Res., 2010; 2(1): 415-423.

A. A. Spasov, I. N. Yozhitsa, L. A. Burhaeva. Pharm. Chem. J. 1999; 33:232-43.

M. A. Philips. J. Chem. Soc. 1928: JR 9280002393:2393.

R. V. Shingalapur, K. M. Hosamani. Catal. Lett. 2010; 137(1-2):63-68,

B. Yadagiri, J. W. Lown. Synth. Comm.1990; 20:955.

P. N. Preston Eds. A. Weissberger, E. C. Taylor. Wiley: New York 1981; 40(1):6-60.

M. R. Grimmett Eds.: A. R. Katritzky C. W. Rees. In Comprehensive Heterocyclic Chemistry, Oxford, 1984; 5:457-487.

B. Rajitha, J. V. Madhav, B. S. Kuarm. Arkivoc 2008; 145-150.

H. F. He, Z. Wang, W. Bao. Adv. Syn. Catal. 2010; 352(17):2905.

F. F. Stevens, J. D. Bower. J. Chem. Soc. 1949; 2971.

L. Wang, J. Sheng, H. Tian. Synth. Comm. 2004; 34:4265.

S. B. Rathod, M. K. Lamde, B. R. Arbad. Bull. Kor. Chem. Soc. 2010; 10(3):2835.

G. V. Reddy, N. S. Ramarao, B. A. Narsaiah. Synth. Comm. 2002; 32:2467.

A. Kumar and K. K. Kapoor. J. Chem. Pharm. Res., 2011; 3(6):369-374.

M. H. Sarvari, H. Sharghi. J. of Chem. 2004; 69:6950-6956.

V. Quaschning, J. Deutsch, P. Druska, H. J. Niclas, E. Kemnitz J. of Catal. 1998; 177(2):164-174.

E. Suzuki, Y. Ono. Bull. Chem. Soc. Japan. 1988; 61:1008.

X. Meng, H. Cheng, S. Fujita, Y. Hao, Y. Shang, Y. Yu, S. Cai, F. Zhao, M. Arai. J. of Catal. 2010; 269, 131-139.

B. M. Reddy, M. K. Patil, K. N. Rao, G. K. Reddy. J. Mol. Cat. A: Chem. 2006; 258:302-307.

T. Ito, J. H. Lunsford. Nature 1985, 314, 721.

S. S. Deshpande, R. V. Jayram. Cat. Comm. 2008; 9:186-193.

G. E. Parris, K. Klier. J. of Catal. 1986; 97(2):374-384.

Published

2024-02-15 — Updated on 2024-02-15

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How to Cite

Venkateswarlu, A., Harikrishna, M., & Thriveni, P. (2024). Antitumor Activity and Synthesis of 1, 2-Disubstituted Benzimidazoles in One-Pot Diverse Using Bismuth (III) Trifluoromethanesulfonate as Catalyst. Asian Journal of Pharmaceutical Research and Development, 12(1), 19–31. https://doi.org/10.22270/ajprd.v12i1.1358