Magnetically recoverable nano-crystalline NiFe2O4 catalyzed green and sustainable synthesis of functionalized pyrano-pyrazol, pyrano-coumarin, and 4H-chromene derivatives

Iranian Journal of Catalysis

مقاله 6، دوره 13، شماره 4، اسفند 2023، صفحه 487-497   

نوع مقاله: Articles

شناسه دیجیتال (DOI): 10.30495/ijc.2023.1993771.2041

نویسنده

Koyel Pradhan^*

Department of Chemistry, Gobardanga Hindu College, North 24 Parganas, West Bengal, India

چکیده

Synthesis of pyrano-pyrazol, pyrano-coumarin, and 4H-chromene derivatives has been achieved by the multicomponent reaction of substituted 1,3-diketo compounds, dialkyl acetylene dicarboxylates and alkyl nitrile derivatives in presence of nano-NiFe₂O₄. The nano-NiFe₂O₄ magnetic nanoparticle was prepared by a simple and effective method and characterized by using XRD, HRTEM images, IR, and VSM studies. The green, convenient, and mild protocol provided large access to desired products in almost quantitative yield. High catalytic activity, very low catalyst loading, and high recyclability are the attractive features of the developed protocol. All reactions were easily performed and preceded with high efficiency under very mild conditions avoiding time-consuming, costly catalysts, and tedious workup and purification of process.

کلیدواژه‌ها

Nano-NiFe2O4؛ Multicomponent reaction؛ Pyrano-pyrazol؛ Pyrano-coumarin and 4H-chromene

سایر فایل های مرتبط با مقاله

Supporting Information.pdf

مراجع

[1] F.M. Abdelrazek, P. Metz, O. Kataeva, A. Jaeger, S.F. El-Mahrouky, Arch. Pharm. 340 (2007) 543-548.

[2] N. Foloppe, L.M. Fisher, R. Howes, A. Potter, A.G.S. Robertson, A.E. Surgenor, Bioorg. Med. Chem. 14 (2006) 4792-4802.

[3] A. Kumar, R.A. Maurya, S.A. Sharma, P. Ahmad, A.B. Singh, G. Bhatia, A.K. Srivastava, Bioorg. Med. Chem. Lett. 19 (2009) 6447-6451.

[4] T. Raj, R.K. Bhatia, A. Kapur, M. Sharma, A.K. Saxena, M.P.S. Ishar, Eur. J. Med. Chem. 45 (2010) 790-794.

[5] F.M. Abdelrazek, P. Metz, E.K. Farrag, Arch. Pharm. 337 (2004) 482-485.

[6] T. Symeonidis, K.C. Fylaktakidou, D.J. Hadjipavlou-Litina, K.E. Litinas, Eur. J. Med. Chem. 44 (2009) 5012-5017.

[7] T. Raj, R.K. Bhatia, R.K. Sharma, V. Gupta, D. Sharma, M.P.S. Ishara, Eur. J. Med. Chem. 44, (2009) 3209-3216.

[8] M. Ough, A. Lewis, E.A. Bey, J. Gao, J.M. Ritchie, W. Bornmann, D.A. Boothman, L.W. Oberley, J.J. Cullen, Cancer Biol. Ther. 4 (2005) 102-109.

[9] V.F. De Andrade-Neto, M.O.F. Goulart, J.F. Da Silva Filho, M.J. Da Silva, M.D.C.F.R. Pinto, A.V. Pinto, M.G. Zalis, K.H. Carvalho, A.U. Krettli, Bioorg. Med. Chem. Lett. 14 (2004) 1145-1149.

[10] E. Pérez-Sacau, A. Estévez-Braun, Á.G. Ravelo, D.G. Yapu, A.G. Turba, Chem. Biodivers. 2 (2005) 264-274.

[11] Z. Dong, X. Liu, J. Feng, M. Wang, L. Lin, X. Feng, Eur. J. Org. Chem. 1 (2011) 137-142.

[12] E.Y. Schmidt, B.A. Trofimov, N.V. Zorina, A.I. Mikhaleva, I.A. Ushakov, E.V. Skital’tseva, O.N. Kazheva, G.G. Alexandrov, O.A. Dyachenko, Eur. J. Org. Chem. 35 (2010) 6727-6730.

[13] D. Moon, M. Kim, S. Kang, Y. Choi, S. Park, G. Kim, Cancer Lett. 292 (2010) 111-115. [14] S. Hatakeyama, N. Ochi, H. Numata, S. Takano, J. Chem. Soc. Chem. Commun. 17 (1988) 1202-1204.

[15] N.S. Babu, N. Pasha, K.T.V. Rao, P.S.S. Prasad, N. Lingaiah, Tetrahedron Lett. 49 (2008) 2730-2733.

[16] A. Gaplovsky, J. Donovalova, M. Lacova, R. Mracnova, H.M. El-Shaaer, J. Photochem. Photobiol. A Chem. 1-2 (2000) 61-65.

[17] D. Armesto, W.M. Horspool, N. Martin, A. Ramos, C. Seoane, J. Org. Chem. 54 (1989) 3069-3072.

[18] K.C. Nicolaou, J.A. Pfefferkorn, G.Q. Cao, Angew. Chem., Int. Ed. 39 (2000) 734–739.

[19] I.E. Soria-Mercado, A. Prieto-Davo, P.R. Jensen, W. Fenical, J. Nat. Prod. 68 (2005) 904–910.

[20] Y. Moumou, J. Vasseur, F. Trotin, J. Dubois, Phytochemical 62 (1992) 265–278.

[21] F.A. Macias, J.M.G. Molinillo, R.M. Varela, A. Torres, F.R. Fronczek, J. Org. Chem. 59 (1994) 8261–8268.

[22] G. Wurzel, H. Becker, T. Eicher, K. Tiefensee, Planta Med. 31 (1990) 1239–1241.

[23] R.A. Edrada, P. Proksch, V. Wray, L. Witte, L. Van Ofwegen, J. Nat. Prod. 61 (1998) 358–361.

[24] I. Miki, N. Kishibayashi, H. Nonaka, E. Ohshima, H. Takami, H. Obase, A. Ishii, Jpn. J. Pharmacol. 59 (1992) 357–364.

[25] X.H. Lu, Q.W. Shi, Z.H. Zheng, A.B. Ke, H. Zhang, C.H. Huo, Y. Ma, X. Ren, Y.Y. Li, J. Lin, Q. Jiang, Y.C. Gu, H. Kiyota, Eur. J. Org. Chem. (2011) 802–807.

[26] K. Sprogoe, S. Manniche, T.O. Larsen, C. Christophersen, Tetrahedron 61 (2005) 8718–8721.

[27] V.K. Tandon, H.K. Maurya, B. Kumar, V.J. Ram, Synlett 18 (2009) 2992–2996.

[28] M.N. Erichsen, T.H.V. Huynh, B. Abrahamsen, J.F. Bastlund, C. Bundgaard, O. Monrad, A.B. Jensen, C.W. Nielsen, K. Frydenvang, A.A. Jensen, L. Bunch, J. Med. Chem. 53 (2010) 7180-7191.

[29] W. Kemnitzer, J. Drewe, S. Jiang, H. Zhang, C.C. Grundy, D. Labreque, M. Bubenick, G. Attardo, R. Denis, S. Lamothe, H. Gourdeau, B. Tseng, S. Kasibhatla, S.X. Cai, J. Med. Chem. 51 (2008) 417-423.

[30] M. Rueping, E. Sugiono, E. Merino, Chem. Eur. J. 14 (2008) 6329-6332.

[31] A. InWeissberger, E. C. Taylor, in: G.P. Ellis (Eds.), The Chemistry of Heterocyclic Compounds Chromenes, Chromanes and Chromones, John Wiley: New York, 1977, pp 11-139.

[32] M. Boominathan, M. Nagaraj, S. Muthusubramanian, R. V. Krishnakumar, Tetrahedron 67 (2011) 6057-6064.

[33] B. Kazemi, S. Javanshir, A. Maleki, M. Safari, H.R. Khavasi, Tetrahedron Lett. 53 (2012) 6977–6981.

[34] P. Prasanna, S. Perumal, J.C. Menéndez, Green Chem.15 (2013)1292-1299.

[35] P. Borah, P.S. Naidu, S. Majumder, P.J. Bhuyan, RSC Adv. 3 (2013) 20450-20455.

[36] B.C. Gates, Chem. Rev. 95 (1995) 511-522.

[37] A. Hu, G. Yee, T. W. Lin, J. Am. Chem. Soc.127 (2005) 12486-12487.

[38] R. Abu-Reziq, H. Alper, D. Wang, M.L. Post, J. Am. Chem. Soc. 128 (2006) 5279-5282.

[39] C.O. Dalaigh, S.A. Corr, Y. Gunko, S.J. Connon, Angew. Chem., Int. Ed. 23 (2007) 4407-4410.

[40] S. Paul, K. Pradhan, S. Ghosh, S.K. De, A.R. Das, Adv. Synth. Catal. 356 (2014) 1301-1316.

[41] K. Faungnawakij, R. Kikuchi, N. Shimoda, T. Fukunaga, Eguchi, Angew. Chem. Int. Ed. 47 (2008) 9314-9317.

[42] C. Liu, B. Zou, A.J. Rondinone, Z.J. Zhang, J. Am. Chem. Soc. 122 (2000) 6263-6267.

[43] S. Verma, P.A. Joy, Y.B. Khollam, H.S. Potdar, S.B. Deshpande, Mater. Lett. 58 (2004) 1092-1095.

[44] D. Fino, N. Russo, G. Saracco, V. Specchia, Catal. Today 117 (2006) 559-563.

[45] S. Joshi, M. Kumar, S. Chhoker, G. Srivastava, M. Jewariya, V.N. Singh, J. Mol. Struct. 1076 (2014) 55-62.

[46] K. Maaz, S. Karim, A. Mumtaz, S.K. Hasanain, J. Liu, J. L. Duan, J. Magn. Magn. Mater. 322 (2010) 2199-2202.