Pr3+ doped CoFe2O4: A highly efficient, magnetically recoverable and reusable catalyst for one-pot four-component synthesis of multisubstituted pyrroles

الموضوعات : Iranian Journal of Catalysis

Firoz Kalam Khan ¹ (Dr. Rafiq Zakaria Campus, Y.B. Chavan College of Pharmacy, Aurangabad 431001, (M.S.), India.)
Amol Pachpinde ² (Department of Chemistry, Jawahar Art Science and Commerce College, Andur, Osmanabad 413603, (M. S.), India.)
Mallinath Langade ³ (Department of Chemistry, Jawahar Art Science and Commerce College, Andur, Osmanabad 413603, (M. S.), India.)
Kishan Lohar ⁴ (Materials Research Laboratory, Srikrishna Mahavidyalaya Gunjoti, Omerga, Osmanabad 413 613, (M. S.), India.)
Sunil Patange ⁵ (Materials Research Laboratory, Srikrishna Mahavidyalaya Gunjoti, Omerga, Osmanabad 413 613, (M. S.), India.)
Omprakash Bhusnure ⁶ (Department of Quality Assurance, Channabasweshwar Pharmacy College, Latur 413512, (M. S.), India.)
Jaiprakash Sangshetti ⁷ (Dr. Rafiq Zakaria Campus, Y.B. Chavan College of Pharmacy, Aurangabad 431001, (M.S.), India.)

تاريخ الإرسال : 01 الأربعاء , محرم, 1437 تاريخ التأكيد : 07 الجمعة , ربيع الأول, 1437 تاريخ الإصدار : 29 الخميس , ذو القعدة, 1437

الکلمات المفتاحية: Catalyst Reusability, Pr3+ doped CoFe2O4, Multisubstituted pyrroles, Recoverable using magnet,

ملخص المقالة :

A facile and highly efficient one-pot synthesis of multisubstituted pyrrole derivatives is reported via a four-component reaction of amines, aldehydes, acetylacetone and nitromethane using Pr3+ doped CoFe2O4 as a catalyst in solvent free conditions at 90°C. The catalyst is easily recoverable using magnet and could be reused without a significant loss of catalytic activity. Even after five runs for the reaction, the catalytic activity of Pr3+ doped CoFe2O4 was almost the same as that of the freshly used catalyst. The proposed method is advantageous due to its little catalyst loading, short reaction time, catalyst reusability, and excellent yields.

المصادر:

[1] L. Banfi, A. Basso, L. Giardini, R. Riva, V. Rocca, G. Guanti, Eur. J. Org. Chem. 1 (2011) 100-109.
[2] N. Ma, B. Jiang, G. Zhang, S.J. Tu, W. Wever, G. Li, Green Chem. 12 (2010) 1357-1361.
[3] C.L. Floch, E.L. Gall, E. Leonel, J. Koubaaet, T. Martens, P. Retailleau, Eur. J. Org. Chem. 2010 (2010) 5279-5286.
[4] C. Haurena, E.L. Gall, S. Sengmany, T. Martens, M. Troupel, J. Org. Chem. 75 (2010) 2645-2650.
[5] M. Adib, E. Sheikhi, A. Kavoosi, H.R. Bijanzadeh, Tetrahedron 47 (2010) 9263-9269.
[6] W.B. Chen, Z.J. Wu, Q.L. Pei, L.F. Cun, X.M. Zhang, W.C. Yuan, Org. Lett. 12 (2010) 3132-3135.
[7] M.S. Singh, S. Chowdhury, RSC Adv. 2 (2012) 4547-4592.
[8] J.R. Rosien, W. Seichter, M. Mazik, Org. Biomol. Chem. 11 (2013) 6569-6579.
[9] J.T. Manka, A.L. Rodriguez, R.D. Morrison, D.F. Venable, H.P. Cho, A.L. Blobaum, J.S. Daniels, C.M. Niswender, P.J. Conn, C.W. Lindsley, K.A. Emmitte, Bioorg. Med. Chem. Lett. 23 (2013) 5091-5096.
[10] M.Z. Wang, H. Xu, T.W. Liu, Q. Feng, S.J. Yu, S.H. Wang, Z.M. Li, Eur. J. Med. Chem. 46 (2011) 1463-1472.
[11] Y.Q. Yang, Q. Zhang, J.F. Zheng, S.B. Zhang, Polymer 54 (2013) 3254-3260.
[12] D. Bandyopadhyay, S. Mukherjee, J.C. Granados, J.D. Short, B.K. Banik, Eur. J. Med. Chem. 50 (2012) 209-221.
[13] F.P. Ma, P.H. Li, B.L. Li, L.P. Mo, N. Liu, H.J. Kang, Y.N. Liu, Z.H. Zhang, Appl. Catal. A 457 (2013) 34-41.
[14] J.B. Bharate, R. Sharma, S. Aravinda, V.K. Gupta, B. Singh, S.B. Bharate, R.A. Vishwakarma, RSC Adv. 3 (2013) 21736-21742.
[15] S. Madabhushi, V.S. Vangipuram, K.K.R. Mallu, N. Chinthala, C.R. Beeram, Adv. Synth. Catal. 354 (2012) 1413-1416.
[16] G. Pacchioni, Surf. Rev. Lett. 7 (2000) 277-306.
[17] L.D. Pachon, J.H. van Maarseveen, G. Rothenberg, Adv. Synth. Catal. 347 (2005) 811-815.
[18] J.N. Sangshetti, F.A.K. Khan, C.S. Kute, Z. Zaheer, R.Z. Ahmed, Russ. J. Org. Chem. 51 (2015) 69-73.
[19] J.N. Sangshetti, F.A.K. Khan, R.S. Chouthe, Z. Zaheer, R.Z. Ahmed, J. Taibah Univ. Sci. 9 (2015) 548-554.
[20] A.P.G. Nikalje, M.S. Ghodke, F.A.K. Khan, J.N. Sangshetti, Chinese Chem. Lett. 26 (2015) 108-112.
[21] Z. Zaheer, F.A.K Khan, J.N. Sangshetti, R.H. Patil, EXCLI J. 14 (2015), 935-947.
[22] J.N. Sangshetti, N.D. Kokare, S.A. Kotharkar, D.B. Shinde, Chinese Chem. Lett. 19 (2008) 762-766.
[23] J.N. Sangshetti, N.D. Kokare, D.B. Shinde, Chinese Chem. Lett. 18 (2007) 1305-1308.
[24] J.N. Sangshetti, N.D. Kokare, D.B. Shinde, Russ. J. Org. Chem. 45 (2009) 1116-1118.
[25] J.N. Sangshetti, D.B. Shinde, Bioorg. Med. Chem. Lett. 20 (2010) 742-745.
[26] J.N. Sangshetti, S.A.M.K. Ansari, D.B. Shinde, Chinese Chem. Lett. 22 (2011) 163-166.
[27] J.N. Sangshetti, F.A.K. Khan, R.S. Chouthe, M.G. Damale, D.B. Shinde, Chinese Chem. Lett. 25 (2014) 1033-1038.
[28] J.N. Sangshetti, P.P. Dharmadhikari, R.S. Chouthe, B. Fatema, V. Lad, V. Karande, S.N. Darandale, D.B. Shinde, Bioorg. Med. Chem. Lett. 23 (2013) 2250-2253.
[29] A.M. Pachpinde, M.M. Langade, K.S. Lohar, S.M. Patange, S.E. Shirsath, Chem. Phys. 429 (2014) 20-26.
[30] B.L. Li, M. Zhang, H.C. Hu, X. Dub, Z.H. Zhang, New J. Chem. 38 (2014) 2435- 2442.
[31] N. Gupta, K.N. Singh, J. Singh, J. Mol. Liq. 199 (2014) 470-473.
[32] B.L. Li, H.C. Hu, L.P. Mo, Z.H. Zhang, RSC Adv. 4 (2014) 12929-12943.