Document Type : Original Research Article
Authors
Department of Chemistry, University of North Bengal, Darjeeling734013, India
Abstract
Small amount of Zn dust and NaHSO3 was utilized to efficiently synthesize benzimidazole derivatives via one pot reductive cyclocondensation process in water medium at 100oC temperature. Very good to excellent yields in reasonably short reaction times, high atom economy and usage of readily available starting material, operational simplicity and easy workup are the fundamental features of this protocol.
Graphical Abstract
)
Highlights
- One potreaction
- Chemoselective reductive cyclisation reaction.
- Aqueous medium.
- Shorter reaction time.
- Easy reaction set-up.
- Inexpensive, easily available reagent, easily separable by simple filtration.
- Mild reaction condition.
Keywords
Main Subjects
References
[1] G. L. Gravatt, B. C. Baguley, W. R. Wilson, W. A. Denny, DNA-Directed Alkylating Agents. 6. Synthesis and Antitumor Activity of DNA Minor Groove-Targeted Aniline Mustard Analogues of Pibenzimol (Hoechst 33258), Journal of Medicinal Chemistry, 37 (1994) 4338–4345.
[2] R. K. Prichard, S. Ranjan, Anthelmintics, Veterinary Parasitology, 46 (1993) 113–120
[3] J. Horn, The proton-pump inhibitors: similarities and differences, Clinical. Therapeutics, 22 (2000) 266–280.
[4] J. Bhaumik, Z. Yao, K. E. Borbas, M. Taniguchi. J. S. Lindsey, Masked Imidazolyl−Dipyrromethanes in the Synthesis of Imidazole-Substituted Porphyrins. The Journal of Organic Chemistry, 71 (2006) 8807-8817.
[5] V. D. Patil, J. Patil, P. Rege, G. Dere, Mild and Efficient Synthesis of Benzimidazole Using Lead Peroxide Under Solvent-Free Conditions, Synthetic Communication, 41 (2011) 58-62.
[6] F. Hakimi, M. Fallah-Mehrjardi, E. Golrasan, Yttrium Aluminum Garnet (YAG: Al5Y3O12) as an Efficient Catalyst for the Synthesis of Benzimidazole and Benzoxazole Derivatives, Chemical Methodologies, 4(2020) 234-244.
[7] M. Asif, Green Synthesis of Benzimidazole Derivatives: an Overview on Green Chemistry and Its Applications, Chemical Methodologies, 3 (2019) 620-631.
[8] A. Nozarie, Metal-Organic Framework MIL-53(Fe) as a highly efficient reusable catalyst for the synthesis of 2-aryl-1H-benzimidazole, Chemical Methodologies, 3 (2019) 704-712.
[9] S. Sajjadifar, Z. Arzehgar, A. Ghayuri, Zn3(BTC)2 as a Highly Efficient Reusable Catalyst for the Synthesis of 2‐Aryl‐1H‐Benzimidazole, Journal of the Chinese Chemical Society, 65(2017) 205-211.
[10] A. Sajjadi, R. Mohammadi, Fe3O4 magnetic nanoparticles (Fe3O4 MNPs): A magnetically reusable catalyst for synthesis of Benzimidazole compounds, Journal of Medicinal and Chemical Sciences, 2 (2019) 55-58.
[11] M. Abdollahi-Alibeik, M. Moosavifard, FeCl3-Doped Polyaniline Nanoparticles as Reusable Heterogeneous Catalyst for the Synthesis of 2-Substituted Benzimidazoles, Synthetic Communication, 40 (2010) 2686-2695.
[12] S. Ponnala, D. P. Sahu, Iodine‐Mediated Synthesis of 2‐Arylbenzoxazoles, 2‐Arylbenzimidazoles, and 1,3,5‐Trisubstituted Pyrazoles, Synthetic Communication, 36 (2006) 2189-2194.
[13] F. H. Havaldar, G. Mule, B. Dabholkar, Novel Method for the Syntheses of 2-Substituted Benzimidazoles Using Ti(IV) Isopropoxide and Cumene Hydroperoxide, Synthetic. Communication, 41 (2011) 2304-2308.
[14] H. Sharghi, O. Asemani, R. Khalifeh, New One‐Pot Procedure for the Synthesis of 2‐Substituted Benzimidazoles, Synthetic Communication,38 ( 2008) 1128-1136.
[15] C. Mukhopadhyay, P. K. Tapaswi, PEG-mediated catalyst-free expeditious synthesis of 2-substituted benzimidazoles and bis-benzimidazoles under solvent-less conditions, Tetrahedron Letters, 49 (2008) 6237-6240.
[16] J. Yuan, Z. Zhao, W. Zhu, H. Li, X. Qian, Y. Xu, New strategy for the synthesis of 2-phenylbenzimidazole derivatives with sodium perborate (SPB) as oxidant, Tetrahedron, 69 ( 2013) 7026-7030.
[17] G. A. Molander, K. Ajayi, Oxidative Condensations To Form Benzimidazole-Substituted Potassium Organotrifluoroborates, Organic Letters, 14 (2012) 4242-4245.
[18] S. Samanta, S. Das, P. Biswas, Photocatalysis by 3,6-Disubstituted-s-Tetrazine: Visible-Light Driven Metal-Free Green Synthesis of 2-Substituted Benzimidazole and Benzothiazole, Journal of Organic Chemistry, 78 (2013) 11184-11193.
[19] S. M. Inamdar, V. K. More, S. K. Mandal, CuO nano-particles supported on silica, a new catalyst for facile synthesis of benzimidazoles, benzothiazoles and benzoxazoles, Tetrahedron Letters, 54 ( 2013) 579-583.
[20] K. Bahrami, M. M. Khodaei, F. Naali, Mild and Highly Efficient Method for the Synthesis of 2-Arylbenzimidazoles and 2-Arylbenzothiazoles, Journal of Organic Chemistry, 73 (2008) 6835-6837.
[21] B. Das, H. Holla, Y. Srinivas, Efficient (bromodimethyl)sulfonium bromide mediated synthesis of benzimidazoles, Tetrahedron Letters, 48 (2007) 61-64.
[22] S. S. Panda, S. C. Jain, Synthesis of 2-Arylbenzimidazoles in Water, Synthetic Communication, 41 (2011) 729-735.
[23] P. Gogoi, D. Konwar, An efficient and one-pot synthesis of imidazolines and benzimidazoles via anaerobic oxidation of carbon–nitrogen bonds in water, Tetrahedron Letters, 47 ( 2006) 79-82.
[24] A. Dhakshinamoorthy, K. Kanagaraj, K. Pitchumani, Zn2+-K10-clay (clayzic) as an efficient water-tolerant, solid acid catalyst for the synthesis of benzimidazoles and quinoxalines at room temperature, Tetrahedron Letters, 52 (2011) 69-73.
[25] Y. Riadi, R. Mamouni, R. Azzalou, M. E. Haddad, S. Routier, An efficient and reusable heterogeneous catalyst Animal Bone Meal for facile synthesis of benzimidazoles, benzoxazoles, and benzothiazoles, Tetrahedron Letters, 52 (2011) 3492-3495.
[26] V. Kumar, D. G. Khandare, A. Chatterjee, M. Banerjee, DBSA mediated chemoselective synthesis of 2-substituted benzimidazoles in aqueous media, Tetrahedron Letters, 54 (2013) 5505-5509.
[27] J. Lu, B. Yang, Y. Bai, Microwave Irradiation Synthesis of 2-Substituted Benzimidazole Using PPA as a Catalyst Under Solvent-Free Condition, Synthetic Communication, 32 (2002) 3703-3709.
[28] S. Kaul, A. Kumar, B. Sain, A. K. Bhatnagar, Simple and Convenient One‐Pot Synthesis of Benzimidazoles and Benzoxazoles using N,N‐Dimethylchlorosulfitemethaniminium Chloride as Condensing Agent, Synthetic Communication, 37 (2007) 2457-2460.
[29] H. Alinezhad, F. Salehian, P. Biparva, Synthesis of Benzimidazole Derivatives Using Heterogeneous ZnO Nanoparticles, Synthetic Communication, 42 (2012) 102-108.
[30] P. C. Guillermo, B. A. Imelda,G. L. C. Jose, G. E. E. Jose, A. T. Cecilio, Synthesis of Benzimidazoles in Dry Medium, Synthetic Communication, 30 (2000) 2191-2195.
[31] X. Wen, J. E. Bakali, R. Deprez-Poulain, B. Deprez, Efficient propylphosphonic anhydride (®T3P) mediated synthesis of benzothiazoles, benzoxazoles and benzimidazoles Tetrahedron Lett, 53 (2012) 2440-2443.
[32] X. Jing, Q. Zhu, F. Xu, X. Ren, D. Li, C. Yan, Rapid one-pot preparation of 2-substituted benzimidazoles from esters using microwave conditions, Synthetic Communication, 36 (2006) 2597-2601.
[33] L. Wang, S. Jia, H. Tian, C. Qian, An Efficient Procedure for the Synthesis of Benzimidazole Derivatives Using Yb(OTf)3 as Catalyst Under Solvent‐Free Conditions, Synthetic Communication. 34( 2004) 4265-4272.
[34] D. S. VanVliet, P. Gillespie, J. J Scicinski, Rapid one-pot preparation of 2-substituted benzimidazoles from 2-nitroanilines using microwave conditions, Tetrahedron Letters, 46 (2005) 6741-6743.
[35] G. Li, J. Wang, B. Yuan, D. Zhang, Z. Lin, P. Li, H. Huang, Dehydrogenative synthesis of benzimidazoles under mild conditions with supported iridium catalysts, Tetrahedron Letter, 54 (2013) 6934-6936.
[36] T. B. Nguyen, L. Ermolenko, A. Al-Mourabit, Iron Sulfide Catalyzed Redox/Condensation Cascade Reaction between 2-Amino/Hydroxy Nitrobenzenes and Activated Methyl Groups: A Straightforward Atom Economical Approach to 2-Hetaryl-benzimidazoles and –benzoxazoles, Journal of the American Chemical Society, 135 (2013) 118-121.
|
)
