Synthesis, characterization and immobilization of cobalt (III) salen complex on CoFe2O4@SiO2 nanoparticle and their application in the synthesis of di-indolyloxindole
محورهای موضوعی : Iranian Journal of Catalysis
Kaveh Hemmat
1
(Department of Chemistry, College of Sciences, University of Birjand, Birjand 97175-615, Iran.)
Mohammad Ali Nasseri
2
(Department of Chemistry, College of Sciences, University of Birjand, Birjand 97175-615, Iran.)
Ali Allahresani
3
(Department of Chemistry, College of Sciences, University of Birjand, Birjand 97175-615, Iran.)
کلید واژه: Multicomponent, indole, Cobalt ferrite, Isatin, Co(III) salen complex, Di-indolyloxindole,
چکیده مقاله :
The preparation, characterization, and immobilization of cobalt (III) salen complex on CoFe2O4@SiO2 nanoparticle (CoFe2O4@SiO2@ Co(III) salen complex) are described. Co(III) salen complex loaded on ferrite cobalt-silica nanoparticle is characterized by TEM, SEM-EDX, VSM and FT-IR analyses. The efficiency of CoFe2O4@SiO2@Co(III) salen complex as a catalyst was carried out in the 3-indolylation reaction of indole with isatin derivatives in the water at 80 . Di-indolyloxindole was achieved with excellent yield (95%), using indole, isatin, and CoFe2O4@SiO2@Co(III) salen complex within 2 h in water as solvent at 80 . Moreover, the recoverability and reusability of CoFe2O4@SiO2@Co(III) salen complex were investigated.
[1] E.N. Jacobsen, W. Zhang, M.L. Guller, J. Am. Chem. Soc. 113 (1991) 6703-6704.
[2] J. Long, Front. Chem. 7 (2019) 63-69.
[3] Z. Li, K.R. Conser, E.N. Jacobsen, J. Am. Chem. Soc. 115 (1993) 5326-5327.
[4] T. Katsuki, Chem. Rev. 140 (1995) 189-214.
[5] P. Jain, G. Pandey, D. Kumar, S. Chandra, Adv. Sci. Eng. Med. 11 (2019) 144-154.
[6] Y. Kohmura, T. Katsuki Tetrahedron Lett. 42 (2001) 3339-3342.
[7] W. Sun, H. Wang, C. Xia, J. Li, P. Zhao Angew. Chem. Int. Ed. 42 (2003) 1042-1044.
[8] W. Sun, E. Herdtweck, F.E. Kuhn. New J. Chem. 29 (2005) 1577-1580.
[9] E.M. McGarrigle, D.M. Murphy, D.G. Gilheany, Tetrahedron: Asymmetry 15 (2004) 1343-1354.
[10] J.A. Gladysz, Chem. Rev. 102 (2002) 3215-3216.
[11] J.A. Gladysz, Pure Appl. Chem. 73 (2001) 1319-1324.
[12] D.E. De Vos, M. Dams, B.F. Sels, P.A. Jacobs, Chem. Rev. 102 (2002) 3615- 3640.
[13] C.E. Song, S. Lee, Chem. Rev. 102 (2002) 3495-3524.
[14] Q.H. Fan, Y.M. Li, A.S.C. Chan, Chem. Rev. 102 (2002) 3385-3466.
[15] R. Ferreira, M. Silva, C. Freire, B. de Castro, J.L. Figueiredo, Microporous Mesoporous Mater. 38 (2000) 391-401.
[16] R. Ferreira, C. Freire, B. de Castro, A.P. Carvalho, J, Pires, M. Brotas de Carvalho, Eur. J. Inorg. Chem. 11 (2002) 3032-3038.
[17] V. Ramaswamy, M. Sivarama Kirshnan, A.V. Ramaswamy, J. Mol. Catal. A: Chem. 181 (2002) 81-89.
[18] A.R. Silva, C. Freire, B. de Castro, M.M.A. Freitas, J.L. Figueiredo, Microporous Mesoporous Mater. 46 (2001) 211-221.
[19] J. Tong, Z. Li, C. Xia, J. Mol. Catal. A: Chem. 231 (2005) 197-203.
[20] J. Tong, Y. Zhang, Z. Li, C. Xia, J. Mol. Catal. A: Chem. 249 (2006) 47-52.
[21] V. Polshettiwar, R. Luque, A. Fihri, H. Zhu, M. Bouhrara, J.M. Basset, Chem. Rev. 111 (2011) 3036-3075.
[22] L. Hamidipour, F. Farzaneh, M. Ghandi, React. Kinet. Mech. Catal. 107 (2012) 421-433.
[23] H. Zeng, J. Li, J. P. Liu, Z.L. Wang, S. H. Sun, Nature 420 (2002) 395-398.
[24] J. Park, K. An, Y. Hwang, J.G. Park, H.J. Noh, J.Y. Kim, J.H. Park, N.M. Hwang, T. Hyeon, Nat. Mater. 3 (2004) 891-895.
[25] G.C.P. Leite, E.F. Chagas, R. Pereira, R.J. Prado, A.J. Terezo, M. Alzamora, E. Baggio-Saitovitch, J. Magn. Magn. Mater. 324 (2012) 2711-2716.
[26] Q.A. Pankhurst, J. Connolly, S.K. Jones, J. Dobson, J. Phys. D Appl. Phys. 36 (2003) 167-181.
[27] G.V.M. Jacintho, A.G. Brolo, P. Corio, P.A.Z. Suarez, J.C. Rubim, J. Phys. Chem. C 113 (2009) 7684-7691.
[28] K. Gandha, K. Elkins, N. Poudyal, X. Liu, J.P. Liu, Sci. Rep. 4 (2014) 5345-5349.
[29] K. Gandha, N. Poudyal, Q. Zhang, J.P. Liu, IEEE Trans. Magn. 49 (2013) 3273-3281.
[30] Y. Cedeno-Mattei, O. Perales-Perez, Microelectr. J. 40 (2009) 673-676.
[31] B.H. Liu, J. Ding, Z.L. Dong, C.B. Bothroyd, J.H. Yin, J.B. Yi, Phys. Rev. B 74 (2006) 184427-184436.
[32] Q. Song, Z. John Zhang, J. Am. Chem. Soc. 126 (2004) 6164-6168.
[33] Z. F. Zi, Y.P. Sun, X.B. Zhu, Z.R. Yang, J.M. Dai, W.H. Song, J. Magn. Magn. Mater. 321 (2009) 1251-1255.
[34] Y. Yu, A. Mendoza-Garcia, B. Ning, S. Sun, Adv. Mater. 25 (2013) 3090-3094.
[35] Y. Lee, J. Lee, C.J. Bae, J.G. Park, H.J. Noh, J.H. Park, T. Hyeon, Adv. Funct. Mater. 15 (2005) 503-509.
[36] N. Hanh, O.K. Quy, N.P. Thuy, L.D. Tung, L. Spinu, Physica B 327 (2003) 382-384.
[37] R.P. Chaudhary, S.K. Mohanty, A.R. Koymen, Carbon 79 (2014) 67-73.
[38] B.S. Jursic, E.D. Stevens, Tetrahedron Lett. 43 (2002) 5681-5683.
[39] A.M.Sh. El-Sharief, Y.A. Ammar, A. Belal, M.A.M. Sh. El-Sharief, Y.A. Mohamed, A.B.M. Mehany, G.A.M.E. Ali, A. Ragab, Bioorg. Chem. 85 (2019) 399-412.
[40] G. Brahmachari, B. Banerjee, ACS Sustainable Chem. Eng. 2 (2014) 2802-2812.
[41] F.X. Felpin, O. Ibarguren, L. Nassar-Hardy, E. Fouquet, J. Org. Chem. 74 (2009) 1349-1352.
[42] I. Sharma, A. Saxena, C.K. Ojha, C.K.P. Paradasani, R.T. Paradasani, T. Mukherjee, Proc. Indian Acad. Sci.114 (2002) 523-531.
[43] J. Kothandapani, A. Ganesan, G.K. Mani, A.J. Kulandaisamy, J.B. Balaguru Rayappan, S.S. Ganesan, Tetrahedron Lett. 57 (2016) 3472-3475.
[44] J. Saffari, D. Ghanbari, N. Mir, K. Khandan-Barani, J. Ind. Eng. Chem. 20 (2014) 4119-4123.
[45] E. Rafiee, N. Rahpeyma, Chin. J. Catal. 36 (2015) 1342-1349.
[46] L.J. Chen, F.M. Mei, G.X. Li, React. Kinet. Catal. Lett. 98 (2009) 99-105.
[47] J. Yu, Y. Luan, Y. Qi, J. Hou, W. Dong, M. Yang, G. Wang, RSC Adv. 4 (2014) 55028-55035.
[48] A. Allahresani, M.A. Nasseri, J. Chem. Sci. 129 (2017) 343-352.
[49] M. Ma, Y. Zhang, W. Yu, H.Y. Shen, H.Q. Zhang, N. Gu, Colloids Surf. A 212 (2003) 219-226.
[50] C.Y. Haw, C.H. Chia, S. Zakaria, F. Mohamed, S. Radiman, C.H. Teh, P.S. Khiew, W.S. Chiu, N.M. Huang, Ceram. Int. 37 (2011) 451-464.
[51] P.C. Morais, R.L. Santos, A.C.M. Pimenta, R.B. Azevedo, E.C.D. Lima, Thin Solid Films 515 (2006) 266-270.
[52] T. Abou Khalil, S. Boujday, J. Blanchard, L. Bergaoui, Chem. Africa 2 (2019) 77-87.
[53] M.K. Surendra, D. Kannan, M.S. Ramachandra Rao, Mater. Res. Soc. Symp. Proc. 1368 (2011) 1368-1373.
[54] C. Ren, X. Ding, H. Fu, C. Meng, W. Li, H. Hang, RSC Adv. 6 (2016) 72479-72486.
[55] J. Bergman, N. Eklund, Tetrahedron 36 (1980) 1445-1450.
[56] M. Nikpasand, M. Mamaghani, K. Tabatabaeian, H.A. Samimi, Synth. Commun. 40 (2010) 3552–3560.
[57] M. Haghighi, K. Nikoofar, J. Saudi Chem. Soc. 20 (2016) 101–106.
[58] G. Mohammadi Ziarani, R. Moradi, A. Badiei, N. Lashgari, B. Moradi, A. Abolhassani Soorki, J. Taibah Univ. Sci. 9 (2015) 555-563.
[59] K. Alimohammadi, Y. Sarrafi, M. Tajbakhsh, Monatsh. Chem. 139 (2008) 1037–1039.
[60] J. Azizian, A.A. Mohammadi, N. Karimi, M.R. Mohammadizadeh, A.R. Karimi, Catal. Commun. 7 (2006) 752–755.
[61] K. Nikoofar, Z. Khalili, Z. Naturforsch. B 71 (2016) 31-36.
[62] N. Karimi, H. Oskooi, M.M. Heravi, M. Saeedi, M. Zakeri, N. Tavakoli, Chin. J. Chem. 29 (2011) 321-323.
[63] A. Allahresani, B. Taheri, M.A. Nasseri, Res. Chem. Intermed. 44 (2018) 6741-6751.
[64] A. Allahresani, M.A. Nasseri, A. Akbari, B. Zakerinasab, React. Kinet. Mech. Catal. 116 (2015) 249-259.
[65] H. Alinezhad, A.H. Haghighi, F. Salehian, Chin. Chem. Lett. 21 (2010) 183-186.
[66] G.M. Patel, P.T. Deota, Heterocycl. Commun. 19 (2013) 421-424.
[67] B.V. Subba Reddy, N. Rajeswari, M. Sarangapani, Y. Prashanthi, R.J. Ganji, A. Addlagatta, Bioorg. Med. Chem. Lett. 22 (2012) 2460-2463.
[68] K. Rad-Moghadam, S. Gholizadeh, Iran. J. Catal. 4 (2014) 41-47.
[69] J.S. Yadav, B.V. Subba Reddy, K.U. Gayathri, S. Meraj, A.R. Prasad, Synthesis 24 (2006) 4121-4123.
[70] S.Y. Wang, S.J. Ji, Tetrahedron. 62 (2006) 1527-1535.
[71] M.A. Nasseri, B. Zakerinasab, Iran. J. Org. Chem. 5 (2013) 1021-1025.
