The Reaction of Aromatic Amines with Propylene Carbonate Catalyzed by Anion-Cation Cooperativity in Ionic Liquids

doi:10.3724/SP.J.1088.2011.10757

Abstract

Abstract: Ionic liquid 1-butyl-3-methyl-imidazolium acetate ([bmim]OAc) effectively catalyzed the reaction of aromatic amines with propylene carbonate to 5-methyl-3-aryloxazolidin-2-one. The effects of reaction temperature, time, and catalyst amount were investigated in detail. Under the optimized conditions, the yield of 5-methyl-3-phenyl-oxazolidin-2-one was 99%. The effects of cations and anions in ionic liquids were also studied. The cations play important role for the reaction and the catalytic activity follows the order of 1-butyl-3-methyl-imidazolium ([bmim]) > 1, 2-dimethyl-3-butyl imidazolium ([bmmim]) > 1-butyl-pyridinium ([bpy]), which is consistent with the order of hydrogen bond donor ability. Simultaneously, the anions are also crucial to the reaction and the catalytic activity of imidazolium based ionic liquids follows the order OAc > Cl > Br > BPh₄, which is consistent with the order of the hydrogen bond acceptor ability.

Key words: ionic liquid, aromatic amine, propylene carbonate, cooperative catalysis, 5-methyl-3-aryloxazolidin-2-one

ZHANG Li-Feng, YANG Si-Juan, GAO Guo-Hua. The Reaction of Aromatic Amines with Propylene Carbonate Catalyzed by Anion-Cation Cooperativity in Ionic Liquids[J]. Chinese Journal of Catalysis, 2011, 32(12): 1875-1879.

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References

1Moureau F, Wouters J, Vercauteren, D P, Collin S, Evrard G, Durant F, Ducrey F, Koenig J J, Jarreau F X. Eur J Med Chem, 1994, 29: 269
2Mai A, Artico M, Esposito M, Sbardella G, Massa S, Be-fani O, Turini P, Glovannini V, Mondovi B. J Med Chem, 2002, 45: 1180
3Selvakumar N, Srinivas D, Khera M K, Kumar M S, Ma-midi N V S R, Sarnaik H, Chandrasekar C, Rao B S, Ra-heem M A, Das J, Iqbal J, Rajagopalan R. J Med Chem, 2002, 45: 3953
4Park C H, Brittelli D R, Wang C L J, Marsh F D, Gregory W A, Wuonola M A, McRipley R J, Eberly V S, Slee A M, Forbes M. J Med Chem, 1992, 35: 1156
5Brickner S J, Hutchinson D K, Barbachyn M R, Manninen P R, Ulanowicz D A, Garmon S A, Grega K C, Hendges S K, Toops D S, Ford C W, Zurenko G E. J Med Chem, 1996, 39: 673
6孟庆国, 金洁, 刘浚. 中国新药杂志 (Meng Q G, Jin J, Liu J. Chin J New Drugs), 2002, 11: 355
7周宇涵, 苗蔚荣, 程侣柏, 王大翔, 柏再苏. 农药学学报 (Zhou Y H, Miao W R, Cheng L B, Wang D X, Bai Z S. Chin J Pestic Sci), 2001, 3: 71
8Speranza G P, Peppel W J. J Org Chem, 1958, 23: 1922
9Gulbins K, Hamann K. Chem Ber, 1961, 94: 3287
10Herweh J E, Kauffman W J. Tetrahedron Lett, 1971, 12: 809
11Herweh J E, Foglia T A, Swern D. J Org Chem, 1968, 33: 4029
12Baba A, Shibata I, Masuda K, Matsuda H. Synthesis, 1985: 1144
13Shibata I, Baba A, Iwasaki H, Matsuda H. J Org Chem, 1986, 51: 2177
14Wu H Y, Ding J C, Liu Y K. J Indian Chem Soc, 2003, 80: 36
15Qian C T, Zhu D M. Synlett, 1994: 129
16Barsa E A, Richter R. J Org Chem, 1986, 51: 4483
17Slocomebdeg R J, Hardy E E, Saunders J H, Jenkins R L. J Am Chem Soc, 1950, 72: 1888
18彭新高, 李福伟, 胡霄雪, 夏春谷, Sandoval C A. 催化学报 (Peng X G, Li F W, Hu X X, Xia Ch G, Sandoval C A. Chin J Catal), 2008, 29: 638
19Cacchi S, Fabrizi G, Goggiamani A, Zappia G. Org Lett, 2001, 3: 2539
20Mallesham B, Rajesh B M, Reddy P R, Srinivas D, Trehan S. Org Lett, 2003, 5: 963
21Chen Y J, Chen H H. Org Lett, 2006, 8: 5609
22Mino T, Harada Y, Shindo H, Sakamoto M, Fujita T. Synlett, 2008: 614
23Jammi S, Sakthivel S, Rout L, Mukherjee T, Mandal S, Mitra R, Saha P, Punniyamurthy T. J Org Chem, 2009, 74: 1971
24Gong H, Yang N F. Heterocycles, 2009, 78: 2093
25Gong H, Yang N F, Deng G J, Xu G Y. Chem Lett, 2009, 38: 584
26Fu X L, Zhang Z, Li C M, Wang L B, Ji H Y, Yang Y, Zou T, Gao G H. Catal Commun, 2009, 10: 665
27Zhang L F, Yang Y, Xue Y R, Fu X L, An Y, Gao G H. Catal Today, 2010, 158: 279
28Zhang L F, Fu X L, Gao G H. ChemCatChem, 2011, 3: 1359
29Chakraborti A K, Roy S R. J Am Chem Soc, 2009, 131: 6902
30Yang Y, Wang L B, Zhang Z, Li C M, Fu X L, Gao G H. Chem Res Chin Univ, 2010, 26: 554

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