Fe3O4@SiO2-SO3H as a recyclable heterogeneous nanomagnetic catalyst for the one-pot synthesis of substituted quinolines via Friedländer heteroannulation under solvent-free conditions

Beyki, Monire; Fallah-Mehrjardi, Mehdi

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Fe3O4@SiO2-SO3H as a recyclable heterogeneous nanomagnetic catalyst for the one-pot synthesis of substituted quinolines via Friedländer heteroannulation under solvent-free conditions

Article 82, Volume 5, Issue 4. pp. 374-500, Autumn 2017, Page 374-383 PDF (858 K)

Document Type: Original Research Article

Authors

Monire Beyki; Mehdi Fallah-Mehrjardi

Department of Chemistry, Payame Noor University, PO BOX 19395-4697 Tehran, Iran.

Abstract

An efficient method has been developed for the Friedländer synthesis of substituted quinolines through a condensation reaction of 2-aminoaryl ketones with α-methylene ketones in the presence of a catalytic amount of nano Fe3O4@SiO2-SO3H under solvent-free conditions at 110 °C. The reactions are completed in short times, and the products are obtained in good to excellent yields. The results revealed several advantages to our procedure, including high product yields, short reaction time, facile work-up procedure, simplicity in operation, eco-friendly reaction conditions, reusability of the catalyst and green aspects by avoiding toxic catalysts and solvents. The catalyst could simply be separated and recovered from the reaction mixture by an external magnet and reused in subsequent reactions without significant loss in activity.

Fe3O4@SiO2-SO3H as a recyclable heterogeneous nanomagnetic catalyst for the one-pot synthesis of substituted quinolines via Friedländer heteroannulation under solvent-free conditions

Keywords

Fe3O4@SiO2-SO3H; quinolines; Friedländer reaction; Solvent-free; recyclable nanomagnetic catalyst; Green chemistry

Main Subjects

Organic chemistry

References

[1] Y. Morimoto, F. Matsuda, H. Shirahama, Synlett, 1991, 202-203.

[2] J.P. Michael, Nat. Prod. Rep., 1997, 14, 605-618.

[3] D.G. Markees, V.C. Dewey, G.W. Kidder, J. Med. Chem., 1970, 13, 324-326.

[4] S.F. Campbell, J.D. Hardstone, M.J. Palmer, J. Med. Chem., 1998, 31, 1031-1035.

[5] M.P. Maguire, K.R. Sheets, K. McVety, A.P. Spada, A. Zilberstein, J. Med. Chem., 1994, 37, 2129-2137.

[6] Y.-L. Chen, K.-C. Fang, J.-Y. Sheu, S.-L. Hsu, C.-C. Tzeng, J. Med. Chem., 2001, 44, 2374-2377.

[7] M. Balasubramanian, J.G. Keay, In Comprehensive Heterocyclic Chemistry II. A.R. Katritzky, C.W. Rees and E.F.V. Scriven, Eds., Pergamon: New York, Vol. 5, 1996, p 245.

[8] X. Zhang, A.S. Shetty, S.A. Jenekhe, Macromolecules, 2000, 33, 2069-2082.

[9] S.A. Jenekhe, L. Lu, M.M. Alam, Macromolecules, 2001, 34, 7315-7324.

[10] R.H.F. Manske, M. Kulka, Org. React., 1953, 7, 59-98.

[11] V.V. Kouznetsov, L.Y.V. Mendez, C.M.M. Gomez, Curr. Org. Chem., 2005, 9, 141-146.

[12] L.J. Born, J. Org. Chem., 1972, 37, 3952-3953.

[13] P. Friedländer, Ber. Deutsch Chem. Ges., 1882, 15, 2572-2575.

[14] G.C. Muscia, M. Bollini, J.P. Carnevale, A.M. Bruno, S.E. Asis, Tetrahedron Lett., 2006, 47, 8811-8815.

[15] A. Shaabani, E. Soleimani, Z. Badri, Monatsh Chem., 2006, 137, 181-184.

[16] C.-S. Jia, Z. Zhang, S.-J. Tu, G.-W. Wang, Org. Biomol. Chem., 2006, 4, 104-110.

[17] G.-W. Wang, C.-S. Jia, Y.-W. Dong, Tetrahedron Lett., 2006, 47, 1059-1063.

[18] M. Narasimhulu, T.S. Reddy, K.C. Mahesh, P. Prabhakar, C.B. Rao, Y. Venkateswarlu, J. Mol. Catal. A: Chem., 2007, 266, 114-117.

[19] A. Shaabani, E. Soleimani, Z. Badri, Synth. Commun., 2007, 37, 629-635.

[20] M. Dabiri, M. Baghbanzadeh, M.S. Nikcheh, Monatsh Chem., 2007, 138, 1249-1252.

[21] A. Shaabani, A. Rahmati, Z. Badri, Z. Catal. Commun., 2008, 9, 13-16.

[22] S. Ghassamipour, A.R. Sardarian, Tetrahedron Lett., 2009, 50, 514-519.

[23] M. Barbero, S. Bazzi, S. Cadamuro, S. Dughera, Tetrahedron Lett., 2010, 51, 2342-2344.

[24] A. Hasaninejad, A. Zare, M. Shekouhy, J. Ameri-Rad, Green Chem., 2011, 13, 958-964.

[25] A.R. Kiasat, A. Mouradzadegun, S.J. Saghanezhad, Chin. J. Catal., 2013, 34, 1861-1868.

[26] D.S. Bose, R.K. Kumar, Tetrahedron Lett., 2006, 47, 813-816.

[27] M.A. Zolfigol, P. Salehi, A. Ghaderi, M. Shiri, Catal. Commun., 2007, 8, 1214-1218.

[28] M. Hosseini-Sarvari, Can. J. Chem., 2009, 87, 1122-1126.

[29] S. Sadjadi, S. Shiri, R. Hekmatshoar, Y.S. Beheshtiha, Monatsh Chem., 2009, 140, 1343-1347.

[30] S. Genovese, F. Epifano, M.C. Marcotullio, C. Pelucchini, M. Curini, Tetrahedron Lett., 2011, 52, 3474-3477.

[31] S.S. Palimkar, S.A. Siddiqui, T. Daniel, R.J. Lahoti, K.V. Srinivasan, J. Org. Chem., 2003, 68, 9371-9378.

[32] F. Sadri, A. Ramazani, A. Massoudi, M. Khoobi, R. Tarasi, A. Shafiee, V. Azizkhani, L. Dolatyari, S.W. Joo, Green Chem. Lett. Rev., 2014, 7, 257-264.

[33] A. Amoozadeh, M. Malmir, N. Koukabi, S. Otokesh, J. Chem. Res., 2015, 39, 694-697.

[34] M. Shabanian, M. Khoobi, F. Hemati, H.A. Khonakdar, S.E. Sadat ebrahimi, U. Wagenknecht, A. Shafiee, J. Ind. Eng. Chem., 2015, 24, 211-218.

[35] M. Khoobi, S.F. Motevalizadeh, Z. Asadgol, H. Forootanfar, A. Shafiee, M.A. Faramarzi, Mater. Chem. Phys., 2015, 149, 77-86.

[36] N. Dayyani, S. Khoee, A. Ramazani, Eur. J. Med. Chem., 2015, 98, 190-202.

[37] R. Meghyasi, J. Safaei-Ghomi, M.A. Sharif, J. Chem. Res., 2016, 40, 397-399.

[38] R.S. Varma, Green Chem., 1999, 1, 43-55.

[39] F. Nemati, M.M, Heravi, R. Saeedi Rad, Chin. J. Catal., 2012, 33, 1825-1831.

[40] A.R. Kiasat, J. Davarpanah, J. Mol. Catal. A: Chem., 2013, 373, 46-54.

[41] H. Naeimi, Z.S. Nazifi, J. Nanopart. Res., 2013, 15, 2026-2037.

[42] A. Khorshidi, S. Shariati, M. Aboutalebi, N. Mardazad, Iran. Chem. Commun., 2016, 4, 142-145

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