Scopus (CiteScore 2022 =3.0, Q3) , ISC

Document Type : Original Research Article

Authors

1 Bu-Ali Sina University- Hamedan- Iran

2 Department of Chemistry, University of Sayyed Jamaleddin Asadabadi, Asadabad, 6541835583, Iran

3 Department of Chemistry, Sayyed Jamaleddin Asadabadi University, Asadabad, 6541835583, Iran

4 department of chemistry, University of Freiburg, Germany

10.33945/SAMI/ECC.2020.1.3

Abstract

Nano-ferrous ferric oxide (nano-Fe3O4) successfully applied as an efficient and heterogeneous catalyst for the synthesis of 1,8-dioxo-decahydroacridines by the condensation reaction of dimedone with aromatic aldehydes and ammonium acetate or aniline derivatives under mild and solvent-free conditions. Also, optimization of the reaction condition was investigated using the response surface method {Central Composite Design (CCD)} compared to empirical research.

Graphical Abstract

Programming of Fe-catalyzed cascade Knoevenagel-Michael-cyclocondensation reaction: create out pseudo acridine derivatives under solvent free conditions

Keywords

[1] a) A.R. Moosavi-Zare, M.A. Zolfigol, O. Khaledian, V. Khakyzadeh, M.D. Farahani, M.H. Beyzavi, H.G. Kruger, Chem. Engin. J., 2014, 248, 122-127; b) A.R. Moosavi-Zare, H. Goudarziafshar, Z. Jalilian, Prog. Chem. Biochem. Res., 2019, 2, 59-63.
[2] A.R. Moosavi-Zare, M.A. Zolfigol, R. Salehi-Moratab, E. Noroozizadeh, J. Mol. Catal. A. Chem., 2016, 415, 144-150.
[3] A.R. Moosavi-Zare, M.A. Zolfigol, S. Farahmand, A. Zare, A.R. Pourali, R. Ayazi-Nasrabadi, Synlett., 2014, 25, 193-196.
[4] A. Khazaei, A.R. Moosavi-Zare, H. Afshar-Hezarkhani, V. Khakyzadeh, RSC Adv, 2014, 4, 32142-32147.
[5] A.R. Moosavi-Zare, M.A. Zolfigol, M. Daraei, Synlett, 2014, 25, 1173-1177.
[6] S. Shylesh, V. Schunemann, W. R. Thiel, Angew. Chem. Int. Ed, 2010, 49, 3428-3459.
[7] Y. Zhu,  L.P. Stubbs, F. Ho, R. Liu, C.P. Ship, J.A. Maguire, N.S. Hosmane, Chem. Cat. Chem., 2010, 2, 365-374.
[8] V. Polshettiwar, R.S. Varma, Org. Biomol. Chem, 2009, 7, 37-40.
[9] K.S. Lee, M.H. Woo, H.S. Kim, E. Y. Lee, I.S.  Lee, Chem. Commun., 2009, 25, 3780-3782.
[10] V. Polshettiwar, Á. Molnár, Tetrahedron, 2007, 63, 6949-6976.
[11] M. Ma, Q. Zhang, D. Yin, J. Dou, H. Zhang, H. Xu, Catal Commun., 2012, 17, 168-172.
[12] L.M. Rossi, I.M. Nangoi, N.J.S. Costa, Inorg. Chem., 2009, 48, 4640-4642.
[13] M.A. Zolfigol, V. Khakyzadeh, A. R. Moosavi-Zare, A. Zare, P. Arghavani-Hadi, Z. Mohammadi, M.H. Beyzavi, S. Afr. J. Chem., 2012, 65, 280-285.
[14] M.A. Zolfigol, A.R. Moosavi-Zare, P. Moosavi, V. Khakyzadeh, A. Zare, C. R. Chimie., 2013, 16, 962-966.
[15] A. Davoodnia, A. Zare-Bidaki, H. Behmadi, Chin. J. Catal, 2012, 33, 1797-1801.
[16] K. Venkatesan, S.S. Pujari, K.V. Srinivasan, Synth. Commun., 2009, 39, 228-241.
[17] T.S. Jin, J.S. Zhang, T.T. Guo, A.Q. Wang, T.S. Li, Synthesis, 2004, 2001-2005.
[18] S. Rostamizadeh, A. Amirahmadi, N. Shadjou, A.M. Amani, J. Heterocyclic Chem., 2012, 49, 111-115.
[19] B. Das, P. Thirupathi, I. Mahender, V.S. Reddy, Y.K. Rao, J. Mol. Catal. A. Chem., 2006, 247, 233-239.
[20] M. Dabiri, M. Baghbanzadeh, E. Arzroomchilar, Catal. Commun., 2008, 9, 939-942.
[21] W. Shen, L.M. Wang, H. Tian, J. Tang, J.J. Yu, J. Fluorine Chem., 2009, 130, 522-527.
[22] A. Davoodnia, H. Norouzi, N. Tavakoli-Hoseini, A. Zare-Bidaki, Synth. React. Inorg. Met. Org. Chem., 2015, 44, 70.
[23] A. Khazaei, A.R. Moosavi-Zare, Z. Mohammadi, V. Khakyzadeh, J. Afsar, J. Chin. Chem. Soc.2016, 63, 165-170.
[24] M.A. Ghasemzadeh, J. Safaei-Ghomi, H. Molaei, C.R. Chimie., 2012, 15, 969–974.
[25] S. Tu, C .Miao, Y. Gao, F. Fang, Q. Zhuang, Y. Feng, D. Shi, Synlett., 2004, 2, 255-258.
[26] M.A. Zolfigol, N. Bahrami-Nejad, S. Baghery, J. Mol.Liq., 2016, 218, 558-564.
[27] Zh. Obshch. Khim, Chinese J. Catal., 2016, 86, 1412-1418.
[28]. S. Balalaie, F.Chadegani, F.Darviche, H. R. Bijanzadeh, Chinese J Chem., 2009, 27, 1953-1956.
[29] G.H. Mohammadi Ziarani, A. Badiei, M. Hassanzadeh, S. Mousavi, Arab. Jour. Chem., 2011, 7, 335-339.
[30] A.K. Dutta, P. Gogoi, R. Borah, RSC Adv., 2014, 4, 41287-41291.
[31] A. Davoodnia, A. Khojastehnezhad, N. Tavakoli-Hoseini, Bull. Korean Chem. Soc., 2011, 32, 2243-2248.
[32] M.A. Zolfigol, A. Khazaei, A.R. Moosavi-Zare, A. Zare, V. Khakyzadeh, Appl. Catal. A: Gen., 2011, 400, 70-81. 
[33] A.R. Moosavi-Zare, M. A. Zolfigol, Z. Rezanejad, Can. J. Chem., 2016, 94, 626-630.
[34] A.R. Moosavi-Zare, M.A. Zolfigol, V. Khakyzadeh, C. Bottcher, M.H. Beyzavi, A. Zare, A. Hasaninejad, R. Luque, J. Mater. Chem. A., 2014, 2, 770-777.
[35] A.R. Moosavi-Zare, M.A. Zolfigol, M. Zarei, A. Zare, V. Khakyzadeh, J. Mol. Liq., 2013, 186, 63-69.
[36] A. Khazaei, M.A. Zolfigol, A.R. Moosavi-Zare, F. Abi, A. Zare, H. Kaveh, V. Khakyzadeh, M. Kazem-Rostami, A. Parhami, H. Torabi-Monfared, Tetrahedron, 2013, 69, 212-218.
[37] A.R. Moosavi-Zare, M.A. Zolfigol, M. Zarei, A. Zare, V. Khakyzadeh, A. Hasaninejad, Appl. Catal. A: Gen., 2013, 467, 61-68.