Trifluoroacetate-bonded polyethylene graphene oxide composite as a novel and efficient catalyst for the synthesis of benzimidazoles under solvent-free conditions

الموضوعات : Iranian Journal of Catalysis

Esmael Rostami ¹ , Seyed Mahdi Haghayeghi ²

1 - Department of chemistry, Payame Noor University, PO BOX 19395-3697 Tehran, Iran.
2 - Department of chemistry, Payame Noor University, PO BOX 19395-3697 Tehran, Iran.

تاريخ الإرسال : 09 السبت , رمضان, 1441 تاريخ التأكيد : 26 الأحد , جمادى الأولى, 1442 تاريخ الإصدار : 17 الإثنين , رجب, 1442

الکلمات المفتاحية: Benzimidazole, Solvent-free, Graphene oxide, Polyethylene composite, trifluoroacetic acid catalyst,

ملخص المقالة :

A green and efficient trifluoroacetate-bonded polyethylene graphene oxide composite was utilized in this research to prepare benzimidazoles with good to excellent yield under a solvent-free condition. The trifluoroacetate-bonded polyethylene graphene oxide composite was constructed by polyethylene/diethylenetriamine-functionalized graphene oxide composite bonded by 2-aminothiazole and CF3COOHmoieties. Fourier transform infrared (FTIR) spectroscopy, X-ray diffraction (XRD) analysis, field emission scanning electron microscopy (FESEM), energy dispersive x-ray spectroscopy (EDS), and thermogravimetric analysis (TGA) were also employed to characterize the composite. Benzimidazoles were synthesized by reacting 1,2-phenylenediamine with aromatic aldehydes in the presence of composite (0.02 g) under solvent-free conditions at 75°C. The composite was recovered and used in five runs without considerable loss of activity. Compared to the other catalysts employed for the synthesis of benzimidazole, the present composite (catalyst) benefits from a series of advantages such as cost-effectiveness, easy storage and handling, recoverability and durability, environmental friendliness, non-metallic nature, and ease of disposal. The present synthetic route has also some advantages, including, moderate condition, easy workup, solvent-free nature, and environmental safety.

المصادر:

[1] R. A. Sheldon, Curr. Opin. Green Sustain. Chem. 18 (2019) 13-19.

[2] N. Jiao, S. S. Stahl, eds., Green Oxidation in Organic Synthesis. John Wiley & Sons, (2019), Incorporated.

[3] M. Burgman, M. Tennant, N. Voulvoulis, K. Makuch, K.Madani, Curr. Opin. Green Sustain. Chem. 13 (2018) 130-136.

[4] M. Hu, Z. Yao, X. Wang, Ind. Eng. Chem. Res. 56 (2017) 3477-3502.

[5] B. Qiu, M. Xing, Zhang, J. Chem. Soc. Rev. 47 (2018) 2165-2216.

[6] M. Hussain, R. A. Naqvi, N. Abbas, S. M. Khan, S. Nawaz, A. Hussain, N. Zahra, M. W. Khalid, Polymers 12 (2020) 323.

[7] T. K. Glaser, O. Plohl, A. Vesel, U. Ajdnik, N. P. Ulrih, M. K. Hrnčič, U. Bren, L. Fras Zemljič, Materials 12 (2019) 2118.

[8] A. M. Ganie, A. M. Dar, F. A. Khan, B. A. Dar, Mini-Rev. Med. Chem. 19 (2019) 1292-1297.

[9] S. Tahlan, S. Kumar, B. Narasimhan, BMC Chem. 13 (2019) 101.

[10] B. Maiti, K. Chanda, RSC Adv. 6 (2016) 50384-50413.

[11] M. Hamiduzzaman, S. J. Mannan, A. Dey, S. M. Abdur Rahman, Der Pharm. Lett. 6 (2014) 47-53.

[12] J. Ramprasad, N. Nayak, U. Dalimba, P. Yogeeswari, D. Sriram, S. K. Peethambar, R. Achur, H. S. S. Kumar, Eur. J. Med. Chem. 95 (2015) 49-63.

[13] T. Pan, X. He, B. Chen, H. Chen, G. Geng, H. Luo, H. Zhang, C. Bai, Eur. J. Med. Chem. 95 (2015) 500-513.

[14] A. P. Nikalje, M. Ghodke, World J. Pharm. Pharm. Sci. 3 (2013) 1311-1322.

[15] N. K. Prashant, K. R. Kumar, Inter. J. Pharm. Tech. Res. 8 (2015) 60-63.

[16] H. Panwar, R. Dubey, N. Chaudhary, T. Ram, Der Pharm. Chem. 5 (2013) 192-200.

[17] A. Patil, S. Ganguly, S. Surana, Rasayan J. Chem. 1 (2008) 447-460.

[18] Y. T. Wang, Y. J. Qin, N. Yang, Y. L. Zhang, C. H. Liu, H. L. Zhu, Eur. J. Med. Chem. 99 (2015) 125-137.

[19] A. Kulshreshtha, Inter. J. Res-Granthaalayah 3 (2015) 1-7.

[20] S. Singhal, P. Khanna, S. S. Panda, L. Khanna, J. Heterocycl. Chem. 56 (2019) 2702-2729.

[21] M. A. Chari, D. Shobha, T. Sasaki, Tetrahedron Lett. 52 (2011) 5575–5580.

[22] R. Trivedi, S. K. De, R. A. Gibbs, J. Mol. Catal. A-Chem. 245 (2006) 8-11.

[23] C. Stevenson, R.J.H. Davies, Chem. Res. Toxicol. 12 (1999) 38–45.

[24] A. Saberi, Iran. J. Sci. Technol. 39 (2015) 7–10.

[25] F. F. Bamoharram, M. M. Heravi, M. Hosseini, K. Bakhtiarib, Iran. J. Org. Chem. 1 (2008) 25-27.

[26] B. G. Mohamed, A.-A. M. Abdel-Alim, M.A. Hussein, Acta Pharm. 56 (2006) 31–48.

[27] G. Mariappan, R. Hazarika, F. Alam, R. Karki, U. Patangia, S. Nath, Arab. J. Chem. 8 (2015) 715–719.

[28] A. Patil, S. Ganguly, S. Surana, Rasayan J. Chem. 1 (2008) 447–460.

[29] S. Rithe, R. Jagtap, S. Ubarhande, Rasayan J. Chem. 8 (2015) 213–217.

[30] Z. H. Zhang, T. S. Li, J. J. Li, Monatsh. Chem. 138 (2007) 89-94.

[31] H. Sharma, N. Kaur, N. Singh, D. O. Jang, Green Chem. 17 (2015) 4263-4270.

[32] A. V. Narsaiah, A. R. Reddy, J. S. Yadav, Synth. Commun. 41 (2010) 262-267.

[33] M. Lei, L. Ma, L. Hu, Synth. Commun. 42 (2012) 2981-2993.

[34] G. Navarrete‐Vázquez, H. Moreno‐Diaz, S. Estrada‐Soto, M. Torres‐Piedra, I. León‐Rivera, H. Tlahuext, O. Muñoz‐Muñiz, H. Torres‐Gómez, Synth. Commun. 37 (2007) 2815-2825.

[35] H. Sharghi, O. Asemani, R. Khalifeh, Synth. Commun. 38 (2008) 1128-1136.

[36] V. K. Tandon, M. Kumar, Tetrahedron Lett. 45 (2004) 4185-4187.

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

[38] K. B. Dhopte, R. S. Zambare, A. V. Patwardhan, P. R. Nemade, RSC Adv. 6 (2016) 8164-8172.

[39] P. K. Dhiman, R. K. Mahajan, I. Kaur, J. Appl. Polym. Sci. 121 (2011) 2584-2590.

[40] M. Pervaiz, P. Oakley, M. Sain, Mater. Sci. Appl. 5 (2014) 845-856.

[41] M. Y. Abdelaal, E. H. Elmossalamy, S. O. Bahaffi, Am. J. Polym. Sci. 2 (2012) 102-108.

[42] W. S. Hummers, R. E. Offeman, J. Am. Chem. Soc. 80 (1958) 1339.

[43] R. Muzyka, M. Kwoka, Ł. Smędowski, N. Díez, G. Gryglewicz, New Carbon Mater. 32 (2017) 15-20.

[44] M. Saeedi, F. Goli, M. Mahdavi, G. Dehghan, M.A. Faramarzi, A. Foroumadi, A. Shafiee, Iran J. Pharm. Res. 13 (2014) 881-892.

[45] J. R. Araujo, M. R. Vallim, M. A. S. Spinacé, M. A. De Paoli, J. Appl. Polym. Sci. 110 (2008) 1310-1317.

[46] J. S. Park, Y. M. Lim, Y. C. Nho, Materials 9 (2016) 13.

[47] A. Alizadeh, G. Abdi, M.M. Khodaei, M. Ashok kumar, J. Amirian, RSC Adv. 7 (2017) 14876-14887.

[48] J. X. Wong, S. N. Gan, M. J. Aishah, Sains Malays. 40 (2011) 771-779.

[49] I. Yilgor, E. Yilgor, I. G. Guler, T. C. Ward, G. L. Wilkes, Polymer 47 (2006) 4105-4114.

[50] M. Grundwald-Wyspianska, M. Szafran, J. Mol. Liq. 33 (1987) 245-254.

[51] H. N. Karade, B. N. Acharya, M. Sathe, M. P. Kaushik, Med. Chem. Res. 17 (2008) 19-29.

[52] N. Singh, U. S. Sharma, N. Sutar, S. Kumar, U. K. Sharma, J. Chem. Pharm. Res. 2 (2010) 691-698.

[53] S. A. Soomro, I. H. Gul, H. Naseer, S. Marwat, M. Mujahid, Curr. Nanosci. 15 (2019) 420-429.

[54] G. Tadayyon, S. M. Zebarjad, S. A. Sajjadi, J. Thermoplast. Compos. Mater. 25 (2012) 479-490.

[55] R. Arrigo, P. Jagdale, M. Bartoli, A. Tagliaferro, G. Malucelli, Polymers 11 (2019) 1336.

[56] J.  Lu, B. Yang, Y. Bai, Synth. Commun. 32 (2002) 3703–3709.

[57] B. Eren, Y. Bekdemir, Quim. Nova 37 (2014) 643-647.

[58] D. Yang, X. Zhu, W. Wei, N. Sun, L. Yuan, M. Jiang, J. You, H. Wang, RSC Adv. 4 (2014) 17832-17839.

[59] G. Navarrete-Va´ zquez, H. Moreno-Diaz, S. Estrada-Soto, M. Torres- Piedra, I. Leo´ n-Rivera, H. Tlahuext, O. Mun˜ oz-Mun˜ iz, H. Torres-Go´ mez, Synth. Commun. 37 (2007) 2815–2825.

[60] B. Das, B. S. Kanth, K. R. Reddy, A. S. Kumar, J. Heterocycl. Chem. 45 (2008) 1499- 1502.

[61] M. R. DeLuca, S. M. Kerwin, Tetrahedron 53 (1997) 457.

[62] A. Ben-Alloum, K. Bougrin, M. Soufiaoui, Tetrahedron Lett. 44 (2003) 5935.

[63] E. Rostami, S. Hamidi Zare, ChemistrySelect 4 (2019) 13295-13303.

[64] R. Afsharpour, S. Zanganeh, S. Kamantorki, F. Fakhraei, E. Rostami, Asian J. Nanosci. Mater. 3 (2020) 148-156.

[65] M. R. Nabid, Y. Bide, M. Jafari, Polym. Degrad. Stabil. 169 (2019) 108962.

[66] G. M. Martins, T. Puccinelli, R. A. Gariani, F. R. Xavier, C. C. Silveira, S. R. Mendes, Tetrahedron Lett. 58 (2017) 1969–1972.

[67] C. Chaudhari, S. M. A. Hakim Siddiki K. Shimizu, Tetrahedron Lett. 56 (2015) 4885–4888.

[68] J. Zhu, Z. Zhang, C. Miao, W. Liu, W. Sun, Tetrahedron 73 (2017) 3458–3462.

[69] P. Linga Reddy, R. Arundhathi, M. Tripathi, D. S. Rawat, RSC Adv. 6 (2016) 53596–53601.

[70] D. Yang, X. Zhu, W. Wei, N. Sun, L. Yuan, M. Jiang, J. You, H. Wang, RSC Adv. 4 (2014) 17832–17839.