n-Octyl-3-methylpipyridinium bromide ([OMePPy]+Br-): novel ionic liquid to promote green synthesis of polycyclic fused acridines

Document Type : Articles

Authors

Department of Chemistry, Faculty of Physics & Chemistry, Alzahra University, Tehran, Iran

Abstract

In this research, various polycyclic fused acridines were synthesized via the highly efficient and green one-step four-component reaction between isatins, dimedone, various amines, and dimethylacetylenedicarboxylates (DMAD/DEAD) in the presence of n-octyl-3-methylpipyridinium bromide ([OMePPy]+Br-) as a newly prepared ionic liquid, in absolute green situations at room temperature under solvent-free conditions. The ionic liquid characterized by 1H NMR, 13C NMR, GC-MASS, TGA/ DTG, EDX, and FESEM techniques. Utilizing an eco-friendly and simply synthesized ionic liquid, green and economic reaction media, and preparing a wide range of polycyclic fused acridines in good yields are some highlighted aspects of the reported protocol.

Graphical Abstract

n-Octyl-3-methylpipyridinium bromide ([OMePPy]+Br-): novel ionic liquid to promote green synthesis of polycyclic fused acridines

Highlights

  • Synthesis of acridines in the presence of ([OMePPy]+Br-) as an ionic liquid, in absolute green situations at room temperature.
  • Synthesizing a novel ionic liquid, n-octyl-3-methylpipyridinium bromide ([OMePPy]+Br-), form available substrates via a simple procedure.  
  • The ionic liquid ([OMePPy]+Br-) characterized by 1H NMR, 13C NMR, GC-MASS, TGA/ DTG, EDX, and FESEM techniques.
  • Performing a benign MCR by utilizing an eco-friendly and simply synthesized IL, in green and economic reaction media.

Keywords


[1] Z. Toobaei, R. Yousefi, F.Panahi, S. Shahidpour, M. Nourisefat, M. M. Doroodmand, A. Khalafi-Nezhad, Carbohydr. Res. 411 (2015) 22-32.
[2] G. Cholewiñski, K. Dzierzbicka, A. M. Koodziejczyk, Pharmacol. Rep. 63 (2011) 305-336.
[3] G. Mehes, H. Nomura, Q. Zhang, T. Nakagawa, Ch. Adachi, Angew. Chem. Int. Ed. 51 (2012) 11311-11315.
[4] I. Antonini, P. Polucci, L. R. Kelland, E. Menta, N. Pescalli, S. Martel, J. Med. Chem. 42 (1999) 2535-2541.
[5] I. Antonini, Curr. Med. Chem. 9 (2002) 1701-1716.
[6] S. Dollinger, S. Löber, R. Klingenstein, C. Korth, P. Gmeiner, J. Med. Chem. 49 (2006) 6591-6595.
[7] B. B. Patel, R. G. Patel, M. P. Patel, J. Serb. Chem. Soc. 71 (2006) 1015-1023.
[8] Y. J. Zhou, D. Sh. Chen, Y. L. Li, Y. Liu, X. Sh. Wang, ACS Comb. Sci. 15 (2013) 498-502.
[9] W. T. Zhang, J. Sun, H. Zhu, R. X. Yue, Y. Zhang, F.-X. Niu, L. Rong, J. Heterocycl. Chem. 57 (2020) 1912-1924.
[10] A. V. Chate, S. P. Kamdi, A. N. Bhagat, J. N. Sangshetti, Ch. H. Gill, Synth. Commun. 48 (2018) 1701-1714.
[11] H. Mohammadi, H. R. Shaterian, Res. Chem. Intermed. 46 (2020) 1109-1125.
[12] F. Noori Sadeh, N. Hazeri, M. T. Maghsoodlou, M. Lashkari, Iran. J. Sci. Technol. Trans. Sci. 42 (2018) 1253-1258.
[13] A. D. Sonawane, D. R. Garud, T. Udagawa, Y. Kubota, M. Koketsu, New J. Chem. 42 (2018) 15315-15324.
[14] J. Zhang, W. Fan, J. Ding, B. Jiang, Sh. Tu, G. Li, Heterocycles 88 (2014) 1065-1077.
[15] B. Jiang, X. Wang, H. W. Xu, M. S. Tu, Sh. Tu, G. Li, Org. Lett. 15 (2013) 1540-1543.
[16] B. Jiang, X. Wang, M. Y. Li, Q. Wu, Q. Ye, H. W. Xu, Sh. Tu, Org. Biomol. Chem. 10 (2012) 8533-8538.
[17] R. Ghorbani-Vaghei S. M. Malaekehpoor, J. Iran. Chem. Soc. 7 (2010) 957-964.
[18] S. R. Mousavi, H. Rashidi Nodeh, A. Foroumadi, Polycycl. Aromat. Comp. (2019) https://doi.org/10.1080/10406638.2019.1616305
[19] D. S. Bhagat, S. U. Tekale, A. K. Dhas, S. U. Deshmukh, R. P. Pawar, P. S. Kendrekar, Org. Prep. Proced. Int. 51 (2019) 96-101
[20] P. Sarkar, Ch. Mukhopadhyay, Green Chem. 17 (2015) 3452-3465.
[21] R. L. Vekariya, J. Mol. Liq. 227 (2017) 44-60.
[22] A. D. Sawant, D. G. Raut, N. B. Darvatkar, M. M. Salunkhe, Green Chem. Lett. Rev. 4 (2011) 41-54.
[23] B. Karimi, M. Tavakolian, M. Akbari, F. Mansouri, ChemCatChem 10 (2018) 3173-3205.
[24] R. M. Lennine, A. S. Wender, Curr. Green Chem. 3 (2016) 120-132.
[25] K. N. Marsh, A. Deev, A. C-T. Wu, E. Tran, A. Klamt, Korean J. Chem. Eng. 19 (2002) 357-362.
[26] N. Kaur, Mini Rev. Org. Chem. 14 (2017) 3-23.
[27] M. Honarmand, A. Tzani, A. Detsi, J. Mol. Liq. 290 (2019) 111358-111365.
[28] K. Nikoofar, Y. Shahedi, F. Jame Chenarboo, Mini Rev. Org. Chem. 16 (2019) 102-110.
[29] K. Nikoofar, H. Heidari, Y. Shahedi, Cellulose 25 (2018) 5697-5709.
[30] K. Nikoofar, F. Mehrikaram, Polyhedron 159 (2019) 330-336.
[31] Z. Khademi, K. Nikoofar, F. Shahriyari, Curr. Org. Synth. 16 (2019) 38-69.
[32] K. Nikoofar, S. Sh. Peyrovebaghi, Res. Chem. Intermed. 45 (2019) 4287-4298.