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以离子液体1-丁基-3-甲基咪唑乙酸盐([bmim]OAc)为催化剂,以芳香胺和碳酸丙烯酯为原料,一步合成了5-甲基-3-芳基噁唑烷-2-酮.系统考察了反应温度、反应时间以及催化剂用量对反应性能的影响.在优化的反应条件下,5-甲基-3-苯基噁唑烷-2-酮的收率可达99%.研究了离子液体阴阳离子结构对反应性能的影响,发现不同阳离子离子液体的催化活性顺序为1-丁基-3-甲基咪唑([bmim])>1,2-二甲基-3-丁基咪唑([bmmim])>1-丁基吡啶([bpy]),与其中阳离子在催化过程中提供氢键的能力一致;不同阴离子离子液体的催化活性顺序为OAc> C1> Br> BPh4,与其中阴离子在催化过程中接受氢键的能力一致.离子液体阴阳离子协同催化芳香胺与碳酸丙烯酯的反应.离子液体[bmim]OAc催化剂可重复使用5次,其活性未见明显下降.

参考文献

[1] Moureau F;Wouters J;Vercauteren;D P Collin S Evrard G Durant F Ducrey F Koenig J J Jarreau F X .[J].European Journal of Medicinal Chemistry,1994,29:269.
[2] Mai A;Artico M;Esposito M;Sbardella G Massa S Befani O Turini P Glovannini V Mondovi B .[J].Journal of Medicinal Chemistry,2002,45:1180.
[3] Selvakumar N;Srinivas D;Khera MK;Kumar MS;Mamidi RN;Sarnaik H;Charavaryamath C;Rao BS;Raheem MA;Das J;Iqbal J;Rajagopalan R .Synthesis of conformationally constrained analogues of linezolid: structure-activity relationship (SAR) studies on selected novel tricyclic oxazolidinones.[J].Journal of Medicinal Chemistry,2002(18):3953-3962.
[4] Park 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].Journal of Medicinal Chemistry,1992,35:1156.
[5] Brickner 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].Journal of Medicinal Chemistry,1996,39:673.
[6] 孟庆国,金洁,刘浚.(口/恶)唑烷酮类抗菌剂研究进展[J].中国新药杂志,2002(05):355-359.
[7] 周宇涵,苗蔚荣,程侣柏,王大翔,柏再苏.N-芳基FDDB唑烷酮类化合物的合成及其除草活性[J].农药学学报,2001(03):71-73.
[8] Speranza G P;Peppel W J .[J].Journal of Organic Chemistry,1958,23:1922.
[9] Gulbins K;Hamann K .[J].Chemische Berichte,1961,94:3287.
[10] Herweh J E;Kauffman W J .[J].Tetrahedron Letters,1971,12:809.
[11] Herweh J E;Foglia T A;Swern D .[J].Journal of Organic Chemistry,1968,33:4029.
[12] Baba A;Shibata I;Masuda K;Matsuda H.[J].Synthesis,1985:1144.
[13] Shibata I;Baba A;Iwasaki H;Matsuda H .[J].Journal of Organic Chemistry,1986,51:2177.
[14] Wu H Y;Ding J C;Liu Y K .[J].JIndian Chem Soc,2003,80:36.
[15] Qian C T;Zhu D M.[J].Synlett:Accounts and Rapid Communications In Synthetic Organic Chemistry,1994:129.
[16] Barsa E A;Richter R .[J].Journal of Organic Chemistry,1986,51:4483.
[17] Slocomebdeg R J;Hardy E E;Saunders J H;Jenkins R L .[J].Journal of the American Chemical Society,1950,72:1888.
[18] 彭新高,李福伟,胡霄雪,夏春谷,Christian A. SANDOVAL.Pd(Oac)2/[mmim]I催化体系胺氨化羰化合成氨基甲酸酯、脲和 2-(噁)唑啉酮[J].催化学报,2008(07):638-642.
[19] Cacchi S;Fabrizi G;Goggiamani A;Zappia G .[J].Organic Letters,2001,3:2539.
[20] Mallesham B;Rajesh B M;Reddy P R;Srinivas D Trehan S .[J].Organic Letters,2003,5:963.
[21] Chen YJ;Chen HH .1,1,1-tris(hydroxymethyl)ethane as a new, efficient, and versatile tripod ligand for copper-catalyzed cross-coupling reactions of aryl iodides with amides, thiols, and phenols[J].Organic letters,2006(24):5609-5612.
[22] Mino T;Harada Y;Shindo H;Sakamoto M;Fujita T .Copper-catalyzed N-arylation of amides and azoles using phosphine-free hydrazone ligands[J].Synlett,2008(4):614-620.
[23] Jammi, S;Sakthivel, S;Rout, L;Mukherjee, T;Mandal, S;Mitra, R;Saha, P;Punniyamurthy, T .CuO Nanoparticles Catalyzed C-N, C-O, and C-S Cross-Coupling Reactions: Scope and Mechanism[J].The Journal of Organic Chemistry,2009(5):1971-1976.
[24] Gong H;Yang N F .[J].Heterocycles,2009,78:2093.
[25] Gong H;Yang N F;Deng G J;Xu G Y .[J].Chemistry Letters,2009,38:584.
[26] Fu X L;Zhang Z;Li C M;Wang L B Ji H Y Yang Y Zou T Gao G H .[J].Catalyst Communication,2009,10:665.
[27] Zhang L F;Yang Y;Xue Y R;Fu X L An Y Gao G H .[J].Catalysis Today,2010,158:279.
[28] Zhang L F;Fu X L;Gao G H .[J].ChemCatChem,2011,3:1359.
[29] Chakraborti A K;Roy S R .[J].Journal of the American Chemical Society,2009,131:6902.
[30] Yang Y;Wang L B;Zhang Z;Li C M Fu X L Gao G H .[J].Chemical Research in Chinese Universities,2010,26:554.
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