Triethylamine-bonded sulfonic acid {[Et3N-SO3H]Cl} as an efficient and homogeneous catalyst for the synthesis of 12-aryl-8,9,10,12-tetrahydrobenzo[a]xanthen-11-ones

Iranian Journal of Catalysis

مقاله 3، دوره 2، شماره 3، آذر 2012، صفحه 107-114   

نویسندگان

Abdolkarim Zare^{* 1}؛ Roghayyeh Khanivar¹؛ Maria Merajoddin¹؛ Masoud Kazem-Rostami²؛ Mohammad Mahdi Ahmad-Zadeh¹؛ Ahmad Reza Moosavi-Zare³؛ Alireza Hasaninejad⁴

¹Department of Chemistry, Payame Noor University, PO BOX 19395-4697, Tehran, Iran

²Young Researchers Club, Takestan Branch, Islamic Azad University, Takestan, Iran

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

⁴Department of Chemistry, Faculty of Sciences, Persian Gulf University, Bushehr 75169, Iran

چکیده

Brønsted acidic ionic liquid triethylamine-bonded sulfonic acid {[Et3N-SO3H]Cl} efficiently catalyzes the one-pot multi-component condensation of 2-naphthol with arylaldehydes and dimedone (5,5-dimethylcyclohexane-1,3-dione) under solvent-free conditions to afford 12-aryl-8,9,10,12-tetrahydrobenzo[a]xanthen-11-ones in high yields and relatively short reaction times.

کلیدواژه‌ها

Brønsted acidic ionic liquid؛ Triethylamine-bonded sulfonic acid {[Et3N-SO3H]Cl}؛ 12-Aryl-8؛ 9؛ 10؛ 12-tetrahydrobenzo[a]xanthen-11-one؛ 2-Naphthol؛ Arylaldehyde؛ Dimedone (5؛ 5-dimethylcyclohexane-1؛ 3-dione)

مراجع

[1] J. M. Jamison, K. Krabill, A. Hatwalkar, E. Jamison, C.C. Tsai, Cell Biol. Int. Rep. 12 (1990) 1075-1084.

[2] T. Hideo, Jpn. Tokkyo Koho JP 56005480, 1981; Chem. Abstr. 95 (1981) 80922b.
[3] J.P. Poupelin, G. Saint-Rut, O. Foussard-Blanpin, G. Narcisse, G. Uchida-Ernouf, R. Lacroix, Eur. J. Med. Chem. 13 (1978) 67-71.
[4] R.M. Ion, D. Frackowiak, A. Planner, K. Wiktorowicz, Acta Biochim. Pol. 45 (1998) 833-845.
[5] S. De, S. Das, A. Girigoswami, Spectrochim. Acta A: Mol. Biomol. Spect. 8 (2005) 1821-1833.
[6] C.G. Knight, V. Stephens, Biochem. J. 258 (1989) 683-687.
[7] J. Li, L. Lu, W. Su, Tetrahedron Lett. 51 (2010) 2434-2437.
[8] G.C. Nandi, S. Samai, R. Kumar, M.S. Singh, Tetrahedron 65 (2009) 7129-7134.
[9] J. Li, W. Tang, L. Lu, W. Su, Tetrahedron Lett. 49 (2008) 7117-7120.
[10] J.M. Khurana, D. Magoo, Tetrahedron Lett. 50 (2009), 4777-4780.
[11] H.J. Wang, X.Q. Ren, Y.Y. Zhang, Z.H. Zhang, J. Braz. Chem. Soc. 20 (2009) 1939-1943.
[12] L.P. Mo, H.L. Chen, J. Chin. Chem. Soc. 57 (2010) 157-161.
[13] A. Kumar, S. Sharma, R.A. Maurya, J. Sarkar, J. Comb. Chem. 12 (2010) 20-24.
[14] M.M. Heravi, H. Alinejhad, K. Bakhtiari, M. Saeedi, H.A. Oskooie, F.F. Bamoharram, Bull. Chem. Soc. Ethiop. 25 (2011) 399-406.
[15] R.Z. Wang, L.F. Zhang, Z.S. Cui, Synth. Commun. 39 (2009) 2101-2107.
[16] S.J. Park, G. Keum, S.B. Kang, H.Y. Koh, Y. Kim, D.H. Lee, Tetrahedron Lett. 39 (1998) 7109-7112.
[17] J. Zhu, H. Bienayme, Multicomponent Reactions, Wiley-VCH, Weinheim, Germany (2005).
[18] A. Hasaninejad, M. Shekouhy, N. Golzar, A. Zare, M.M. Doroodmand, Appl. Catal. A: Gen. 402 (2011) 11-22.
[19] F. Tamaddon, M. Farahi, B. Karami, J. Mol. Catal. A: Chem. 356 (2012) 85-89.
[20] M. Smith, J. March, March's advanced organic chemistry: reactions, mechanisms, and structure, Wiley (2007).
[21] F. Tamaddon, F. Aboee, A. Nasiri, Catal. Commun. 16 (2011) 194-197.
[22] A. Hasaninejad, A. Zare, M. Shekouhy, J. Ameri-Rad, Green Chem. 13 (2011) 958-964.
[23] Z. Gordi, H. Eshghi, Iran. J. Catal. 1 (2011) 25-29.
[24] P. Wasserscheid, T. Welton, Ionic Liquids in Synthesis, Wiley-VCH, Weinheim (2008).
[25] R.D. Rogers, K.R. Seddon, Ionic Liquids: Industrial Applications to Green Chemistry, American Chemical Society, Washington DC (2002).
[26] A. Hasaninejad, A. Zare, M. Shekouhy, J. Ameri Rad, J. Comb. Chem. 12 (2010) 844-849.
[27] J.A. Whitehead, G. A. Lawrance, A. McCluskey, Green Chem. 6 (2004) 313-315.
[28] L. Khazdooz, A. Zarei, A. R. Hajipour, N. Sheikhan, Iran. J. Catal. 1 (2011) 1-9.
[29] 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.
[30] R. Kore, T.J.D. Kumar, R. Srivastava, J. Mol. Catal. A: Chem. 360 (2012) 61-70.
[31] 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.
[32] A. Khazaei, M.A. Zolfigol, A.R. Moosavi-Zare, A. Zare, M. Khojasteh, Z. Asgari, V. Khakyzadeh, A. Khalafi-Nezhad, Catal. Commun. 20 (2012) 54-57.