Preparation, characterization and testing the catalytic activity of a new acidic ionic liquid in multicomponent reactions

Iranian Journal of Catalysis

مقاله 8، دوره 7، شماره 3، آذر 2017، صفحه 233-241   

نوع مقاله: Articles

نویسندگان

Abdolkarim Zare^* ؛ Elaheh Sharif؛ Azam Arghoon؛ Marzieh Ghasemi؛ Bentolhoda Dehghani؛ Sorayya Ahmad-Zadeh؛ Fatemeh Zarei

Department of Chemistry, Payame Noor University, PO BOX 19395-3697, Tehran, Iran.

چکیده

In this study, N¹,N¹,N²,N²-tetramethylethane-1,2-diamine was reacted with chlorosulfonic acid to afford N¹,N¹,N²,N²-tetramethyl-N¹,N²-bis(sulfo)ethane-1,2-diaminium chloride ([TMBSED][Cl]₂) as a new acidic ionic liquid. [TMBSED][Cl]₂ was identified by ¹H and ¹³C NMR, mass and FT-IR spectra. Then, its catalytic activity was examined to promote the following multicomponent reactions: (i) the production of 4,4´-(arylmethylene)-bis(3-methyl-1-phenyl-1H-pyrazol-5-ol)s from arylaldehydes and 3-methyl-1-phenyl-1H-pyrazol-5(4H)-one in ethanol, and (ii) the synthesis of 12-aryl-8,9,10,12-tetrahydrobenzo[a]xanthen-11-ones from arylaldehydes, dimedone and 2-naphthol in solvent-free conditions. The ionic liquid was highly efficient and general catalyst for these reactions.

کلیدواژه‌ها

Acidic ionic liquid؛ [TMBSED][Cl]2؛ 4,4´-(Arylmethylene)-bis(3-methyl-1-phenyl-1H-pyrazol-5-ol)؛ 12-Aryl-8,9,10,12-tetrahydrobenzo[a]xanthen-11-one

مراجع

[1] L. Youseftabar-Miri, M. Rafieirad, Iran. J. Catal. 5 (2015) 15-19.
[2] R. Tayebee, M. Jomei, B. Maleki, M. Kargar Razi, H. Veisi, M. Bakherad, J. Mol. Liq. 206 (2015) 119-128.
[3] L. Khazdooz, A. Zarei, Iran. J. Catal. 6 (2016) 69-74.
[4] 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. 167 (2012) 69-77.
[5] A.R. Hajipour, N. Sheikhan, M.A. Alaei, A. Zarei, Iran. J. Catal. 5 (2015) 231-236.
[6] M.A. Zolfigol, A. Khazaei, A.R. Moosavi-Zare, A. Zare, H.G. Kruger, Z. Asgari, V. Khakyzadeh, M. Kazem-Rostami, J. Org. Chem. 77 (2012) 3640-3645.
[7] A.R. Moosavi-Zare, M.A. Zolfigol, M. Zarei, A. Zare, J. Afsar, Appl. Catal. A 505 (2015) 224-234.
[8] D.M. Bailey, P.E. Hansen, A.G. Hlavac, E.R. Baizman, J. Pearl, A.F. Defelice, M.E. Feigenson, J. Med. Chem. 28 (1985) 256-260.
[9] L.C. Behr, R. Fusco, C.H. Jarboe, A. Weissberger (Ed.), The Chemistry of Heterocyclic Compounds, Pyrazoles, Pyrazolines, Pyrazolidines, Indazoles, and Condensed Rings, New York, Interscience, 1967.
[10] K. Sujatha, G. Shanthi, N.P. Selvam, S. Manoharan, P.T. Perumal, M. Rajendran, Bioorg. Med. Chem. Lett. 19 (2009) 4501-4503.
[11] P.M.S. Chauhan, S. Singh, R.K. Chatterjee, Ind. J. Chem. Sect. B 32 (1993) 858-861.
[12] A.B. Uzoukwu, S.S. Al-Juaid, P.B. Hitchcock, J.D. Smith, Polyhedron 12 (1993) 2719-2724.
[13] M.A. Gouda, J. Heterocycl. Chem. 53 (2016) 356-376.
[14] M. Barge, R. Salunkhe, RSC Adv. 4 (2014) 31177-31183.
[15] Z. Karimi-Jaberi, B. Pooladian, M. Moradi, E. Ghasemi, Chin. J. Catal. 33 (2012) 1945-1949.
[16] A. Zare, F. Abi, V. Khakyzadeh, A.R. Moosavi-Zare, A. Hasaninejad, M. Zarei, Iran. J. Catal. 5 (2015) 311-320.
[17] B. Sadeghi, M. Ghorbani Rad, Iran. J. Catal. 4 (2014) 67-70.
[18] A. Hasaninejad, A. Zare, M. Shekouhy, N. Golzar, Org. Prep. Proced. Int. 43 (2011) 131-137.
[19] M. Keshavarz, M. Vafaei-Nezhad, Catal. Lett. 146 (2016) 353-363.
[20] S. Tayebi, K. Niknam, Iran. J. Catal. 2 (2012) 69-74.
[21] J.P. Poupelin, G. Saint-Ruf, O. Foussard-Blanpin, G. Marcisse, G. Uchida-Ernouf, R. Lacroix, Eur. J. Med. Chem. 13 (1978) 67-71.
[22] R.W. Lambert, J.A. Martin, J.H. Merrett, E.B.K. Parkes, G.J. Thomas, PCT Int. Appl. WO 9706178 (1997).
[23] N.P. Buu-Hoi, G. Saint-Ruf, A. De, H.T. Hieu, Bull. Chim. Ther. 7 (1972) 83-86.
[24] A. Banerjee, A.K. Mukherjee, Stain Technol. 56 (1981) 83-85.
[25] R.M. Ion, A. Planner, K. Wiktorowicz, D. Frackowiak, Acta Biochim. Pol. 45 (1998) 833-845.
[26] M. Ahmad, T.A. King, D.-K. Ko, B.H. Cha, J. Lee, J. Phys. D: Appl. Phys. 35 (2002) 1473-1476.
[27] F. Taghavi, M. Gholizadeh, A.S. Saljooghi, M. Ramezani, RSC Adv. 6 (2016) 87082-87087.
[28] S. Vahdat, S. Khaksar, Res. Chem. Intermed. 41 (2015) 4177-4186.
[29] A. Zare, R. Khanivar, M. Merajoddin, M. Kazem-Rostami, M.M. Ahmad-Zadeh, A.R. Moosavi-Zare, A. Hasaninejad, Iran. J. Catal. 2 (2012) 107-114.
[30] A.R. Moosavi-Zare, M.A. Zolfigol, M. Zarei, A. Zare, V. Khakyzadeh, J. Mol. Liq. 211 (2015) 373-380.
[31] Y. Wan, X.-X. Zhang, C. Wang, L.-L. Zhao, L.-F. Chen, G.-x. Liu, S.-Y. Huang, S.-N. Yue, W.-L. Zhang, H. Wu, Tetrahedron 69 (2013) 3947-3950.
[32] K. Tabatabaeian, A. Khorshidi, M. Mamaghani, A. Dadashi, M.K. Jalali, Can. J. Chem. 89 (2011) 623-627.
[33] J.M. Khurana, A. Lumb, A. Chaudhary, B. Nand, RSC Adv. 3 (2013) 1844-1854.
[34] R. Mohammadi, E. Eidi, M. Ghavami, M.Z. Kassaee, J. Mol. Catal. A: Chem. 393 (2014) 309-316.