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

Subject Areas : Iranian Journal of Catalysis

Koyel Pradhan ¹

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

Received: 2023-08-12 Accepted : 2023-10-18 Published : 2023-12-01

Keywords:

References:

[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.