1-(1-Propylsulfonic)-3-methylimidazolium chloride Brønsted acidic ionic liquid catalyzed one-pot synthesis of 14-aryl-14H-dibenzo[a,j]xanthene derivatives under solvent-free conditions
الموضوعات : Iranian Journal of CatalysisSima Abbaspour 1 , Mogharab Torabi Jafroudi 2 , Shima Haghi 3 , Sohan Rezayati 4
1 - Department of Chemistry, Faculty of science, Islamic Azad University, Rasht Branch, Rasht, Iran.
2 - Department of Chemistry, Faculty of science, Islamic Azad University, Rasht Branch, Rasht, Iran.
3 - Department of Chemistry, Payame Noor University, Tehran, P.O. Box 19395-4697, Iran.
4 - Department of Chemistry, Payame Noor University, Tehran, P.O. Box 19395-4697, Iran.
الکلمات المفتاحية: Aldehydes, Xanthenes, 2-Naphthol, One-pot reaction, Reusable catalyst, Ionic Liquids,
ملخص المقالة :
A rapid, green and efficient method for the synthesis of 14-aryl-14H-dibenzo[a,j]xanthene derivatives through a one-pot condensation of 2-naphthol with various aromatic aldehydes in the presences of several acidic ionic liquids including [PSMIM]Cl, [BMIM]HSO4, [BMIM]Cl, [BMIM]Br, and [BMIM]BF4 as organocatalysts and task-specific acidic ionic liquids (AILs) under solvent-free conditions is described. Compared with other synthetic methods, this new method has the advantages such as milder reaction conditions, good to excellent yields, short reaction times, and environmentally benign procedure. Also, 1-(1-Propylsulfonic)-3-methylimidazolium chloride [PSMIM]Cl acts as a catalyst under solvent-free conditions and can be recovered and reused six times without apparent loss of its catalytic activity.
[1] J.D. Holbrey, K.R. Seddon, Clean Prod. Proc. 1 (1999) 233–236.
[2] T. Welton, Chem. Rev. 99 (1999) 2071–2084.
[3] H.L. Ngo, K. LeCompte, L. Hargens, A.B. McEwen, Thermochim. Acta. 357-358 (2000) 97–102.
[4] R.W. Lambert, J.A. Martin, J.H. Merrett, K.E.B. Parkes, PCT Int. Appl. (1997) WO 9706178.
[5] H. Takeshiba, T. Jiyoujima, Japan Tokkyo Koho (1981) JP 56005480.
[6] J.P. Poupelin, G. Saint-Rut, O. Fussard-Blanpin, G. Narcisse, G. Uchida Ernouf, R. Lakroix Eur. J. Med. Chem. 13 (1978) 67–71.
[7] D.C. Neckers, J. Photochem. Photobiol. A 47 (1989) 1-29.
[8] T. Tanaka, Food Chem. Toxicol. 39 (2001) 447–454.
[9] F.M.D. Chequer, V.P. Venancio, M.L.P. Bianchi, L.M.G. Antunes, Food Chem. Toxicol. 50 (2012) 3447–3451.
[10] A. Kumar, S. Sharma, R.A. Maurya, J. Sarkar, J. Comb. Chem. 12 (2010) 20–24.
[11] M. Ahmad, T.A. King, D.K. Ko, B.H. Cha, J. Lee, J. Phys. D: Appl. Phys. 35 (2002) 1473–1476.
[12] C.G. Knight, T. Stephens, Biochem. J. 258 (1989) 683-687.
[13] B. Ravindranath, T.R. Seshadri, Phytochemistry 12 (1973) 2781–2788.
[14] B. Rajitha, B. Sunil Kumar, Y. Thirupathi Reddy, P. Narsimha Reddy, N. Sreenivasulu, Tetrahedron Lett. 46 (2005) 8691–8693.
[15] A. Saini, S. Kumar, J.S. Sandhu, Synlett (2006) 1928–1932.
[16]. M.A. Bigdeli, M.M. Heravi, G.H. Mahdavinia, J. Mol. Catal. A: Chem. 275 (2007) 25–29.
[17] D.W. Knight, P.B. Little, J. Chem. Soc. Perkin Trans. 1. 14 (2001) 1771–1777.
[18] A. Jha, J. Beal, Tetrahedron Lett. 45 (2004) 8999–9001.
[19] G. Casiraghi, G. Casnat, M. Cornia, Tetrahedron Lett. 14 (1973) 679–682.
[20] C.W. Kuo, J.M. Fang, Synth. Commun. 31 (2001) 877–892.
[21] J.Q. Wang, R.G. Harvey, Tetrahedron 58 (2002) 5927–5931.
[22] A.R. Khosropour, M.M. Khodaei, H. Moghannian, Synlett (2005) 955–958.
[23] T.S. Jin, J.S. Zhang, J.C. Xiao, A.Q. Wang, T.S. Li, Synlett (2004) 866–870.
[24] X.S. Wang, D.Q. Shi, Y.L. Li, H. Chen, X.Y. Wei, Z.M. Zong, Synth. Commun. 35 (2005) 97–104.
[25] F. Darvish, S. Balalaei, F. Chadegani, P. Salehi, Synth. Commun. 37 (2007) 1059–1066.
[26] M.A. Pasha, V.P. Jayashankara, Bioorg. Med. Chem. Lett. 17 (2007) 621–623.
[27] L. Nagarapu, S. Kantevari, V.C. Mahankhali, Catal. Commun. 8 (2007)1173–1177.
[28] A. Saini, S. Kumar, J.S. Sandhu, Synlett (2006) 1928–1932.
[29] A. Porcheddu, G. Giacomelli, M. Salaris, J. Org. Chem. 70 (2005) 2163–2361.
[30] A.S. Amarasekara, O.S. Owereh, Ind. Eng. Chem. Res. 48 (2009) 10152–10155
[31] S. Rezayati, S. Sajjadifar, J. Sci. I.R. Iran. 25 (2014) 329–337.
[32] S. Sajjadifar, S. Rezayati, Chem. Pap. 68 (2014) 531–539.
[33] S. Rezayati, R. Hajinasiri, Z. Erfani, Res. Chem. Intermed. DOI: 10.1007/s11164-015-2168-1.
[34] H.S. Haeri, S. Rezayati, E. Rezaee Nezhad, H. Darvishi, Res. Chem. Intermed. DOI: 10.1007/s11164-015-2318-5.
[35] S. Rezayati, F. Sheikholeslami-Farahani, F. Rostami-Charati, S. Afshari Sharif Abad, Res. Chem. Intermed. DOI: 10.1007/s11164-015-2261-5.
[36] S. Rezayati, Z. Erfani, R. Hajinasiri, Chem. Pap. 69 (2015) 536-543.
[37] A. De Andrade Bartolomeu, M.L. De Menezes, L.C. Da Silva Filho, Chem. Pap. 68 (2014) 1593-1600.
[38] J. Venu Madhav, B. Suresh Kuarm, B. Rajitha, Arkivoc II (2008) 204-209.
[39] H.R. Shaterian, A. Hosseinian, M. Ghashang, Turk. J. Chem. 33 (2009) 233–240.
[40] R.J. Sarma, J.B. Baruah, Dyes Pigm. 65 (2005) 91–92.
[41] B. Rajita, B. Sunil Kamar, Y. Thirapathi Reddy, P. Narimha Reddy, N. Sreenivasulu, Tetrahedron Lett. 46 (2005) 8691–8693.
[42] W. Su, D. Yang, C.J. Bo Zhang, Tetrahedron Lett. 49 (2008) 3391–3394.
[43] M. Dabiri, M. Baghbanzadeh, M. Shakouri Nikcheh, E. Arzroomchilar, Bioorg. Med. Chem. Lett. 18 (2008) 436–438.
[44] J.V. Madhav, V.T. Reddy, P.N. Reddy, M.N. Reddy, S. Kuarm, P.A. Crooks, B. Rajitha, J. Mol. Catal. A: Chem. 304 (2009) 85–87.
[45] G. Mohammadi Ziarani, A.R. Badiei, M. Azizi, Sci. Iran. C 18 (2011) 453–457.
[46] J.Z. Karimi, M.M. Hashemi, Monatsh. Chem. 139 (2008) 605–608.
[47] S. Khaksar, N. Behzadi, Chin. J. Catal. 33 (2012) 982–985.
[48] S. Rezayati, Z. Erfani, R. Hajinasiri, Chem. Pap. 69 (2015) 536–543.
