Preparation, characterization and the use of sulfonic acid-functionalized phthalimide (SFP) as a highly efficient and green catalyst for the condensation of arylaldehydes with 2-naphthol
الموضوعات : Iranian Journal of Catalysis
Abdolkarim Zare
1
(Department of Chemistry, Payame Noor University, PO BOX 19395-4697, Tehran, Iran.)
Fatemeh Reghbat
2
(Department of Chemistry, Payame Noor University, PO BOX 19395-4697, Tehran, Iran.)
الکلمات المفتاحية: 2-Naphthol, Solvent-free, Arylaldehyde, Sulfonic acid-functionalized phthalimide (SFP), 14-Aryl-14H-dibnzo[a, j]xanthene,
ملخص المقالة :
Phthalimide was reacted with chlorosulfonic acid to give sulfonic acid-functionalized phthalimide (SFP), which characterized by 1H NMR, 13C NMR, FT-IR, XRD (X-ray diffraction), SEM (scanning electron microscopy), EDX (energy-dispersive X-ray), mass, TG (thermogravimetry) and DTG (derivative thermal gravimetry) spectra. Afterward, its catalytic activity was examined for the condensation of arylaldehydes with 2-naphthol under solvent-free conditions to afford 14-aryl-14H-dibenzo[a,j]xanthenes. The results showed that SFP was highly efficient catalyst to promote the reaction.
[1] G. Mohammadi Ziarani, N. Lashgari, A. Badiei, J. Mol. Catal. A: Chem. 397 (2015) 166-191.
[2] M.M. Heravi, E. Hashemi, F. Azimian, J. Iran. Chem. Soc. 12 (2015) 647-653.
[3] A.R. Moosavi-Zare, M.A. Zolfigol, V. Khakyzadeh, C. Böttcher, M.H. Beyzavi, A. Zare, A. Hasaninejad, R. Luque, J. Mater. Chem. A 2 (2014) 770-777.
[4] A. Khalafi-Nezhad, F. Panahi, S. Mohammadi, H.O. Foroughi, J. Iran. Chem. Soc. 10 (2013) 189-200.
[5] A.R. Moosavi-Zare, M.A. Zolfigol, E. Noroozizadeh, M. Tavasoli, V. Khakyzadeh, A. Zare, New J. Chem. 37 (2013) 4089-4094.
[6] N. Ghaffari Khaligh, F. Shirini, Ultrason. Sonochem. 22 (2015) 397-403.
[7] F. Shirini, M.A. Zolfigol, M. Abedini, J. Iran. Chem. Soc. 7 (2010) 603-607.
[8] 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.
[9] P. Gholamzadeh, G. Mohammadi Ziarani, N. Lashgari, A. Badiei, P.R. Asadiatouei, J. Mol. Catal. A: Chem. 391 (2014) 208-222.
[10] N. Iravani, M. Keshavarz, M. Mousavi, M. Baghernejad, Iran. J. Catal. 5 (2015) 65-71.
[11] T. Hideo, Jpn. Tokkyo Koho JP (1981) 56005480.
[12] J.M. Jamison, K. Krabill, A. Hatwalkar, E. Jamison, C. Tsai, Cell. Biol. Int. Rep. 14 (1990) 1075-1084.
[13] J.P. Poupelin, G. Saint-Ruf, O. Foussard-Blanpin, G. Narcisse, G. Uchida-Ernouf, R. Lacroix, Eur. J. Med. Chem. 13 (1978) 67-71.
[14] S.M. Menchen, S.C. Benson, J.Y.L. Lam, W. Zhen, D. Sun, B.B. Rosenblum, S.H. Khan, M. Taing, U.S. Patent (2003) 6583168.
[15] C.G. Knight, V. Stephens, Biochem. J. 258 (1989) 683-687.
[16] I. Mohammadpoor-Baltork, M. Moghadam, V. Mirkhani, S. Tangestaninejad, H.R. Tavakoli, Chin. Chem. Lett. 22 (2011) 9-12.
[17] B.F. Mirjalili, A. Bamoniri, A. Akbari, N. Taghavinia, J. Iran. Chem. Soc. 8 (2011) S129-S134.
[18] 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. Argoon, R. Roohandeh, J. Mol. Liq. 167 (2012) 69-77.
[19] M. Hong, C. Cai, J. Fluorine Chem. 130 (2009) 989-992.
[20] A. Zare, M. Merajoddin, F. Abi, A.R. Moosavi-Zare, M. Mokhlesi, M.A. Zolfigol, Z. Asgari, V. Khakyzadeh, A. Hasaninejad, A. Khalafi-Nezhad, A. Parhami, J. Chin. Chem. Soc. 59 (2012) 860-865.
[21] W. Su, D. Yang, C. Jin, B. Zhang, Tetrahedron Lett. 49 (2008) 3391-3394.
[22] P.S. Kumar, B.S. Kumar, B. Rajitha, P.N. Reddy, N. Sreenivasulu, Y.T. Reddy, Arkivoc xii (2006) 46-50.
[23] H. Naeimi, Z. S. Nazifi, C.R. Chim. 17 (2014) 41-48.
[24] M.A. Bigdeli, M.M. Heravi, G.H. Mahdavinia, Catal. Commun. 8 (2007) 1595-1598.
[25] A.R. Moosavi-Zare, M.A. Zolfigol, O. Khaledian, V. Khakyzadeh, Chin. J. Catal. 35 (2014) 573-578.
[26] K. Tanaka, Solvent-Free Organic Synthesis, Wiley-VCH, GmbH and KgaA, Weinheim, Germany (2004).
[27] A.R. Moosavi-Zare, Z. Asgari, A. Zare, M.A. Zolfigol, M. Shekouhy, RSC Adv. 4 (2014) 60636-60639.
[28] S.C. Azimi, Iran. J. Catal. 5 (2015) 41-48.
[29] A. Zare, M. Merajoddin, M.A. Zolfigol, Iran. J. Catal. 3 (2013) 83-90
[30] A. Khazaei, M. Khazaei, S. Rahmati, J. Mol. Catal. A: Chem. 398 (2015) 241-247.
[31] R. Ghashghaei, S. Ghassamipour, Iran. J. Catal. 4 (2014) 49-53.
[32] G.B.D. Rao, M.P. Kaushik, A.K. Halve, Tetrahedron Lett. 53 (2012) 2741-2744.
