Design an Efficient Method for the Synthesis of 2-(1,3-Diphenyl-1H-Pyrazol-4-yl)-1H-Benzo[d]imidazole
Published 2020-04-01
Keywords
- Benzoimidazoles,
- pyrazoles,
- imidazoles
Copyright (c) 2020
This work is licensed under a Creative Commons Attribution-ShareAlike 4.0 International License.
Abstract
A simple, highly efficient and environmentally friendly method has been developed for the synthesis of 2-(1,3-diphenyl-1H-pyrazol-4-yl)-1H-benzo[d]imidazole by using Gadolinium(III) trifluoromethanesulfonate catalyst and ethanol reflux reaction conditions By using this method. 12 new 2-(1,3-diphenyl-1H-pyrazol-4-yl)-1H-benzo[d]imidazole derivatives were synthesized under optimized reactions conditions. All these new products structures are confirmed by spectral analysis. By this method, we achieved imidazole derivatives with more operational simplicity, short reaction time and good yields (up to 85%).
References
- Abdel-Wahab, B. F.; Abdel-Aziz, H. A.; Ahmed, E. M. Eur. J. Med.m Chem. 2009, 44, 2632.
- Kaniwa, K.; Ohtsuki, T.; Yamamoto, Y.; Ishibashi, M. Tetrahedron Lett. 2006, 47, 1505.
- Di Nunno, L.; Franchini, C.; Scilimati, A.; Sinicropi, M. S.; Tortorella, P. Tetrahedron: Asymmetry 2000, 11, 1571.
- (a) Moreno-Díaz, H.; Villalobos-Molina, R.; Ortiz-Andrade, R.; Díaz-Coutiño, D.; Medina-Franco, J. L.; Webster, S. P.; Binnie, M.; Estrada-Soto, S.; Ibarra-Barajas, M.; Leon-Rivera, I.; Navarrete- ́ Vazquez, G. ́ Bioorg. Med. Chem. Lett. 2008, 18, 2871.
- Srinivas, B., Devi, N. S., Sreenivasulu, G. K., & Parameshwar, R. Synthesis And Characterization Of Pyrrolo [2, 1-C][1, 4] Benzodiazepine-Circumdatin Conjugates. Heterocyclic Letters, 2015, 5(3), 459-466.
- Srinivas, B., Devi, N. S., Sreenivasulu, G. K., & Parameshwar, R. Synthesis and characterization of quinazolino-benzodiazepine-benzothiazole-hybrid derivatives." Der Pharma Chemica, 2015, 7(5), 251-256.
- Scheetz, M. E.; Carlson, D. G.; Schinitsky, M. R. Infect. Immun. 1977, 15, 145. (c) Ricote, M.; Valledor, A. F.; Glass, C. K. Arterioscler., Thromb., Vasc. Biol. 2004, 24, 230.
- (d) Khurmi, N. S.; Bowles, M. J.; O’Hara, M. J.; Lahiri, A.; Raftery, E. B. Int. J. Cardiol. 1985, 9, 289.
- A.A.O. Sarhan, A. Al-Dhfyan, M.A. Al-Mozaini, C.N. Adra, T.A. Fadl, Cell cycle disruption and apoptotic activity of 3-aminothiazolo[3,2-a]benzimidazole-2-
- carbonitrile and its homologues, Eur. J. Med. Chem. 45 (2010) 2689-2694.
- A.A. El Rashedy, H.Y. Aboul-Enein, Benzimidazole derivatives as potential
- anticancer agents, Mini Rev. Med. Chem. 13 (2013) 399-407.
- Q. Guan, C. Han, D. Zuo, M. Zhai, Z. Li, Q. Zhang, Y. Zhai, X. Jiang, K. Bao, Y. Wu,W. Zhang, Synthesis and evaluation of benzimidazole carbamates bearing indole moieties for antiproliferative and antitubulin activities, Eur. J. Med. Chem. 87 (2014) 306-315.
- A. Husain, M. Rashid, M. Shaharyar, A.A. Siddiqui, R. Mishra, Benzimidazole
- clubbed with triazolo-thiadiazoles and triazolo-thiadiazines: new anticancer agents, Eur. J. Med. Chem. 62 (2013) 785-798.
- K. Paul, S. Bindal, V. Luxami, Synthesis of new conjugated coumarinbenzimidazole hybrids and their anticancer activity, Bioorg. Med. Chem. 15 (2013) 3667e3672.
- Akita, Y.; Inoue, A.; Yamamoto, K.; O Shimizu, M. Heterocycles 1985, 23, 2327.
- Ohkuwa, T.; Chiba, M.; Fukunaga, R.; Miyafuji, N.; Aoyagi, Y. Heterocycles 1990, 31, 1951.
- Srinivas Boddupally, Prashanth Jyothi, Mandava Venkata Basaveswara Rao, Koya Prabhakara Rao. Design and Synthesis of Antimicrobial Active, (E)-(3-(substituted-styryl)-7H-furo[2,3-f]chromen-2-yl)(phenyl)methanone Derivatives and their in Silico Molecular Docking studies. J. Heterocyclic Chem. 2019; 56(1); 73-80.
- Srinivas B, Jettiboina Suryachandram, Katyayani Devi Y, Koya Prabhakara Rao. Synthesis and Antibacterial activity Studies of 8, 9 Di Hydro [7h] Benzo 1,2,4-Oxadiazoles And Its Coumarin Derivatives. J. Heterocyclic Chem. 2017; 54(6); 3730-3734.
- Srinivas B, Jettiboina Suryachandram, Sadanandam P, Rao MVB, Koya Prabhakara Rao. A Facile Synthetic Method for the Synthesis of new 7’,9’dihydrospiro[indoline-2,11’-pyrazolo[3,4-f]pyrimido[4,5-b]quinoline]-3,8’,10’(1’H,6’H)-trione and its Biological Evaluation. Journal of Pharmaceutical Sciences and Research, 2019; 11(5); 1918-1925.
- Devi NS, Srinivas B and Sarangapani M: Synthesis and screening N-(2, 4'-dioxo-1, 2-dihydro-3'H-spiro[indole-3,2'-[1,3]thiazolidin]-3'yl)-2-hydroxybenzamides for anti-bacterial activity. Int J Pharm Sci & Res2019; 10(8): 3850-55
- Devi, N. S., Srinivas, B., & Sarangapani, M. Synthesis and Screening of 3-(4-Oxo-2-Phenyl-1, 3-Thiazol-5 (4h)-Ylidene)-1, 3-Dihydro-2h-Indol-2-One-N-Methylanilines for Antiinflammatory Activity. Journal of Pharmaceutical Sciences and Research, 2019, 11(3), 741-746.
- Parameshwar R, Harinadha Babu. V, Manichandrika. P, Narendra Sharath Chandra JN, Venkata Ramana Reddy M , Srinivas.B "Pyrazole scaffold: a promising tool in the development of antiproliferative agents." Journal of Global Trends in Pharmaceutical Sciences, 2019, 6(3), 2728-2744.
- A. L.; Derridj, F.; Djebbar, S.; Doucet, H. Tetra 2926. (b) Derridj, F.; Roger, J.; Djebbar, S.; D 2010, 12, 4320. (c) Chen, L.; Roger, J.; Brunea Doucet, H. Chem. Commun. 2011, 47, 1872.