Document Type: Short communication

Authors

1 Bu-Ali Sina University- Hamedan- Iran

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

3 Faculty of Chemistry, Bu-Ali Sina University, Hamedan, 6517838683, Iran

Abstract

3-methyl-1-sulfonic acid imidazolium tetrachloroferrate {[Msim]FeCl4} as an efficient sulfur catalyst was prepared and applied, as an efficient catalyst, for the cross-aldol condensation reaction between cycloalkanones and arylaldehydes to give α,αʹ- bis(arylidene)cycloalkanones in high yields and short reaction times at 75 °C under solvent-free conditions.
3-methyl-1-sulfonic acid imidazolium tetrachloroferrate {[Msim]FeCl4} as an efficient sulfur catalyst was prepared and applied, as an efficient catalyst, for the cross-aldol condensation reaction between cycloalkanones and arylaldehydes to give α,αʹ- bis(arylidene)cycloalkanones in high yields and short reaction times at 75 °C under solvent-free conditions.
3-methyl-1-sulfonic acid imidazolium tetrachloroferrate {[Msim]FeCl4} as an efficient sulfur catalyst was prepared and applied, as an efficient catalyst, for the cross-aldol condensation reaction between cycloalkanones and arylaldehydes to give α,αʹ- bis(arylidene)cycloalkanones in high yields and short reaction times at 75 °C under solvent-free conditions.

Graphical Abstract

Keywords

Main Subjects

[1] B.M. Trost, I. Fleming, Comprehensive organic synthesis, 2, Pergamon Press, Oxford, 1991.

[2] R. Mahrwald, D.A. Evans, (Foreword by) (Eds.), Modern Aldol Reactions, Wiley-VCH, Germany, Weinheim, 2004.

[3] N.B. Pathan, A.M. Rahatgaonkar, M.S. Chorghade, Catal. Commun., 2011, 12, 1170-1176.

[4] A. Hasaninejad, A. Zare, L. Balooty, H. Mehregan, M. Shekouhy, Synth. Commun., 2010, 40, 3488-3495.

[5] J. Deli, Pharmazie, 1984, 39, 539-540.

[6] T.P. Robinson, R.B. Hubbard, T.J. Ehlers, J.L. Arbiser, D.J. Goldsmith, J.P. Bowen, Bioorg. Med. Chem., 2005, 13, 4007-4013.

[7] A.T. Dinkova-Kostova, C. Abeygunawardana, P.J. Talalay, Med. Chem., 1998, 41, 5287-5296.

[8] C. Piantadosi, I.H. Hall, J.L. Irvine, G.L. Carlson, J. Med. Chem., 1973, 16, 770-795.

[9] A. Zare, M. Merajoddin, , A. Hasaninejad, A.R. Moosavi-Zare, V. Khakyzadeh, C.R. Chimie, 2013, 16, 380-384.

[10] A.R. Moosavi-Zare, M.A. Zolfigol, M. Zarei, A. Zare, V. Khakyzadeh, J. Mol. Liq., 2013, 186, 63-69.

[11] M.A. Zolfigol, A. Khazaei, A.R. Moosavi-Zare, A. Zare, Organic Preparations and Procedures International, 2010, 42, 95-102.

[12] M.A. Zolfigol, A. Khazaei, A.R. Moosavi-Zare, A. Zare, J. Iran. Chem. Soc., 2010, 7, 646-651.

[13] A. Khazaei, M.A. Zolfigol, A.R. Moosavi-Zare, A. Zare, Scientia Iranica, Transaction C: Chemistry & Chemical Engineering, 2010, 17, 31-36.

[14] M.A. Zolfigol, A. Khazaei, A.R. Moosavi-Zare, A. Zare, H.G. Kruger, Z. Asgari, V. Khakyzadeh, M. Kazem-Rostami, The Journal of Organic Chemistry, 2012, 77, 3640-3645.

[15] A. Khazaei, M.A. Zolfigol, A.R. Moosavi-Zare, A. Zare, E. Ghaemi, V. Khakyzadeh, Z. Asgari, A. Hasaninejad Scientia Iranica, Transaction C: Chemistry & Chemical Engineering, 2011, 18, 1365-1371.

[16] M.A. Zolfigol, V. Khakyzadeh, A. R. Moosavi-Zare, A. Zare, S.B. Azimi, Z. Asgari, A. Hasaninejad, Comptes Rendus Chimie, 2012, 15, 719-736.

[17] A. Khazaei, M.A. Zolfigol, A.R. Moosavi-Zare, Z. Asgari, M. Shekouhy, A. Zare, A. Hasaninejad, RSC Adv., 2012, 2, 8010-8013.

[18] M.A. Zolfigol, V. Khakyzadeh, A. R. Moosavi-Zare, G. Chehardoli, F. Derakhshan-Panah, A. Zare, O. Khaledian, Scientia Iranica, Transaction C: Chemistry & Chemical Engineering, 2012, 19, 1584-1590.

[19] A. Zare, A.R. Moosavi-Zare, M. Merajoddin, M.A. Zolfigol, T. Hekmat-Zadeh, A. Hasaninejad, A. Khazaei, M. Mokhlesi, V. Khakyzadeh, F. Derakhshan-Panah, M.H. Beyzavi, E. Rostami, A. Arghoon, R. Roohandeh, J. Mol. Liq., 2012, 167, 69-77.

[20] a) A. Zare, T. Hekmat-Zadeh, S. Mirzaei-Monfared, M. Merajoddin, H. Torabi-Monfared, M.A. Zolfigol, A.R. Moosavi-Zare, E. Rostami, M. Mokhlesi, F. Derakhshan-Panah, S. Porbahi, S. Balandeh, South African Journal of Chemistry, 2012, 65, 63-68; b) A. Zare, F. Abi, A. R. Moosavi-Zare, M.H. Beyzavi, M.A. Zolfigol, Journal of Molecular Liquids, 2013, 178, 113-121.

[21] M.A. Zolfigol, A. Khazaei, A.R. Moosavi-Zare, A. Zare, V. Khakyzadeh, Appl. Catal. A: Gen., 2011, 400, 70-81.

[22] a) P. Gogoi, A. K. Dutta, P. Sarma, R. Borah, Appl. Catal. A: Gen., 2015, 492,133-139; b) A. Khazaei, A.R. Moosavi-Zare, S. Firoozmand, M.R. Khodadadian, Appl. Organometal. Chem., 2017, DOI:10.1002/jccs.201700211.

[23] A.R. Moosavi-Zare, M.A. Zolfigol, M. Zarei, A. Zare, V. Khakyzadeh, A. Hasaninejad, Appl. Catal. A: Gen., 2013, 467, 61-68.

[24] Y. Wan, X. Mei, L. Pang, R. Ma, C. Yue, C. Yuan, W. Lin, Synth. Commun., 2010, 40, 2320.

[25] G.H. Mahdavinia, M. Mirzazadeh E-J. Chemistry., 2011, 9, 49-54.

[26] A. Habibi, E. Sheikhhosseini, M. Bigdeli, S. Balalaie, E. Farrokhi, Int. J. Org. Chem., 2011, 1, 143-147.

[27] E.J. Eisenbraun, S.M. Mcelvain, J. Am. Chem. Soc., 1955, 77, 3383-3385.

[28] C.R. Conard, M.A. Dolliver, Org. Synth. Coll., 1943, 2, 167.