Citation:
Ahmad Reza Moosavi-Zare, Mohammad Ali Zolfigol, Omid Khaledian, Vahid Khakyzadeh. Condensation of 2-naphtol with arylaldehydes using acetic acid functionalized ionic liquids as highly efficient and reusable catalysts[J]. Chinese Journal of Catalysis,
;2014, 35(4): 573-578.
doi:
10.1016/S1872-2067(14)60030-9
-
An efficient solvent-free protocol for the synthesis of 14-aryl-14H-dibenzo[a,j]xanthenes from the condensation of 2-naphthol with arylaldehydes, using acetic acid functionalized imidazolium salts (1-carboxymethyl-3-methylimidazolium bromide ([cmmim]Br) and 1-carboxymethy1-3-methylimidazolium tetrafluoroborate ([cmmim]BF4) as reusable catalysts, has been developed. The turn over frequency on the catalysts is several times higher than the other previously reported catalysts. Also, thermal gravimetric analysis and powder X-ray diffraction pattern of the catalysts have been studied.
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[1]
[1] Wasserscheid P, Keim W. Angew Chem Int Ed, 2000, 39: 3772
-
[2]
[2] Parvulescu V I, Hardacre C. Chem Rev, 2007, 107: 2615
-
[3]
[3] Earle M J, Katdare S P, Seddon K R. Org Lett, 2004, 6: 707
-
[4]
[4] Ranu B C, Banerjee S. J Org Chem, 2005, 70: 4517
-
[5]
[5] Ranu B C, Adak L, Banerjee S. Can J Chem, 2007, 85: 366
-
[6]
[6] Pegot B, Vo-Thanh G, Gori D, Loupy A. Tetrahedron Lett, 2004, 45: 6425
-
[7]
[7] Zare A, Moosavi-Zare A R, Hasaninejad A, Parhami A, Khalafi-Nezhad A, Beyzavi M H. Synth Commun, 2009, 39: 3156
-
[8]
[8] Zare A, Parhami A, Moosavi-Zare A R, Hasaninejad A, Khalafi-Nezhad A, Beyzavi M H, Can J Chem, 2009, 87: 416
-
[9]
[9] Hasaninejad A, Zare A, Shekouhy M, Ameri Rad J. J Comb Chem, 2010, 12: 844
-
[10]
[10] Zolfigol M A, Khazaei A, Moosavi-Zare A R, Zare A. Org Prep Proced Int, 2010, 42: 95
-
[11]
[11] Zolfigol M A, Khazaei A, Moosavi-Zare A R, Zare A. J Iran Chem Soc, 2010, 7: 646
-
[12]
[12] Khazaei A, Zolfigol M A, Moosavi-Zare A R, Zare A. Sci Iran, Trans C, 2010, 17: 31
-
[13]
[13] Zolfigol M A, Khazaei A, Moosavi-Zare A R, Zare A, Kruger H G, Asgari Z, Khakyzadeh V, Kazem-Rostami M. J Org Chem, 2012, 77: 3640
-
[14]
[14] Zolfigol M A, Khazaei A, Moosavi-Zare A R, Zare A, Khakyzadeh V. Appl Catal A, 2011, 400: 70
-
[15]
[15] Khazaei A, Zolfigol M A, Moosavi-Zare A R, Zare A, Ghaemi E, Khakyzadeh V, Asgari Zh, Hasaninejad A. Sci Iran, Trans C, 2011, 18: 1365
-
[16]
[16] Zolfigol M A, Khakyzadeh V, Moosavi-Zare A R, Zare A, Azimi S B, Asgari Z, Hasaninejad A. C R Chim, 2012, 15: 719
-
[17]
[17] Zare A, Yousofi T, Moosavi-Zare A R. RSC Adv, 2012, 2: 7988
-
[18]
[18] Khazaei A, Zolfigol M A, Moosavi-Zare A R, Asgari Z, Shekouhy M, Zare A, Hasaninejad A. RSC Adv, 2012, 2: 8010
-
[19]
[19] Zolfigol M A, Khakyzadeh V, Moosavi-Zare A R, Chehardoli G, Derakhshan-Panah F, Zare A, Khaledian O. Sci Iran Trans C, 2012, 19: 1584
-
[20]
[20] Zare A, Moosavi-Zare A R, Merajoddin M, Zolfigol M A, Hekmat-Zadeh T, Hasaninejad A, Khazaei A, Mokhlesi M, Khakyzadeh V, Derakhshan-Panah F, Beyzavi M H, Rostami E, Arghoon A, Roohandeh R. J Mol Liq, 2012, 167: 69
-
[21]
[21] Zare A, Hekmat-Zadeh T, Mirzaei-Monfared S, Merajoddin M, Torabi-Monfared H, Zolfigol M A, Moosavi-Zare A R, Rostami E, Mokhlesi M, Derakhshan-Panah F, Porbahi S, Balandeh S. S Afr J Chem, 2012, 65: 63
-
[22]
[22] Zare A, Abi F, Moosavi-Zare A R, Beyzavi M H, Zolfigol M A. J Mol Liq, 2013, 178: 113
-
[23]
[23] Moosavi-Zare A R, Zolfigol M A, Zarei M, Zare A, Khakyzadeh V. J Mol Liq, 2013, 186: 63
-
[24]
[24] Khazaei A, Zolfigol M A. Moosavi-Zare A R, Afsar J, Zare A, Khakyzadeh V, Beyzavi M H. Chin J Catal (催化学报), 2013, 34: 1936
-
[25]
[25] Moosavi-Zare A R, Zolfigol M A, Zarei M, Zare A, Khakyzadeh V, Hasaninejad A. Appl Catal A, 2013, 467: 61
-
[26]
[26] Hideo T. JP Patent 56005480. 1981
-
[27]
[27] Lambert R W, Martin J A, Merrett J H, Parkes K E B, Thomas G J. WO Patent 9706178. 1997
-
[28]
[28] Poupelin J P, Saint-Ruf G, Foussard-Blanpin O, Narcisse G, Uchida-Ernouf G, Lacroix R, Europ J Med Chem, 1978, 13: 67
-
[29]
[29] Ion R M, Planner A, Wiktorowicz K, Frackowiak D. Acta Biochim Pol, 1998, 45: 833
-
[30]
[30] Menchen S M, Benson S C, Lam J Y L, Zhen W G, Sun D Q, Rosenblum B B, Khan S H, Taing M. US Patent 6583168. 2003
-
[31]
[31] Bekaert A, Andrieux J, Plat M. Tetrahedron Lett, 1992, 33: 2805
-
[32]
[32] Alcantara-Licudine J P, Kawate M K, Li Q X. J Agric Food Chem, 1997, 45: 766
-
[33]
[33] Pasha M A, Jayashankara V P. Bioorg Med Chem Lett, 2007, 17: 621
-
[34]
[34] Rajitha B, Kumar B S, Reddy Y T, Reddy P N, Sreenivasulu N. Tetrahedron Lett, 2005, 46: 8691
-
[35]
[35] Hong M, Cai C. J Fluorine Chem, 2009, 130: 989
-
[36]
[36] Sarma R J, Baruah J B. Dyes Pigments, 2005, 64: 91
-
[37]
[37] Khosropour A R, Khodaei M M, Moghannian H. Synlett, 2005: 955
-
[38]
[38] Bhattacharya A K, Rana K C, Mujahid M, Sehar I, Saxena A K. Bioorg Med Chem Lett, 2009, 19: 5590
-
[39]
[39] Shakibaei G I, Mirzaei P, Bazgir A. Appl Catal A, 2007, 325: 188
-
[40]
[40] Mahdavinia G H, Rostamizadeh S, Amani A M, Emdadi Z. Ultrason Sonochem, 2009, 16: 7
-
[41]
[41] Das B, Ravikanth B, Ramu R, Laxminarayana K, Rao B V. J Mol Catal A, 2006, 255: 74
-
[42]
[42] Bigdeli M A, Heravi M M, Mahdavinia G H. J Mol Catal A, 2007, 275: 25
-
[43]
[43] Amini M M, Seyyedhamzeh M, Bazgir A. Appl Catal A, 2007, 323: 242
-
[44]
[44] Bigdeli M A, Heravi M M, Mahdavinia G H. Catal Commun, 2007, 8: 1595
-
[45]
[45] Su W K, Yang D, Jin C, Zhang B. Tetrahedron Lett, 2008, 49: 3391
-
[46]
[46] Makaev F, Styngach E, Shargarovskii V, Bets L, Vlad L, Barba A. Russ J Org Chem, 2010, 46: 610
-
[47]
[47] Fei Z F, Zhao D B, Geldbach T J, Scopelliti R, Dyson P J. Chem Eur J, 2004, 10: 4886
-
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