球磨法促进芳香醛与丙二睛的Knoevenagel缩合反应
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摘要
以芳香醛和丙二睛为原料,NaCl为助磨剂,在无催化剂、无溶剂的条件下,通过球磨反应,以较高的收率合成了一系列Knoevenagel缩合反应产物,产物结构经过1H NMR和MS表征。本方法具有条件温和,后处理简单,环境友好,产率高等优点。
A series of Knoevenagel condensation productions were synthesized from aromatic aldehydes and malononitrile by ball milling in the grinding aid of NaCl without catalyst and solvent. The structures of the productions were confirmed by1 H NMR and MS. The method has mild reaction condition, simple post processing, environmental friendliness and higher yields.
A series of Knoevenagel condensation productions were synthesized from aromatic aldehydes and malononitrile by ball milling in the grinding aid of NaCl without catalyst and solvent. The structures of the productions were confirmed by1 H NMR and MS. The method has mild reaction condition, simple post processing, environmental friendliness and higher yields.
引文
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[2]Borah H N,Deb M L,Boruah R C,et al.Stereoselective intramolecular hetero Diels-Alder reactions of 1-\oxa-1,3-butadienes:synthesis of novel annelated pyrrolo[1,2-a]indoles[J].Tetrahedron Lettt.,2005,46(19):3391-3393.
[3]Narsaiah A V,Basak A K,Visali B,et al.An eco-friendly synthesis of electrophilic alkenes catalyzed by dimethylaminopyridine under solvent-free conditions[J].Synth.Commun.,2004,34(16):2893-2901.
[4]Han J J,Xu Y F,Su Y P,et al.Guanidine-catalyzed Henry reaction and Knoevenagel condensation[J].Catal.Commun.,2008,9(10):2077-2079.
[5]汪昀,任仲皎,曹卫国,等.在固态中合成α-氰基-β-芳基丙烯酰胺[J].上海大学学报,2003,9(1):78-82.
[6]Green B,Crane R I,Khaidem I S,et al.Synthesis of steroidal 16,17-fused unsaturatedδ-lactones[J].J.Org.Chem.,1985,50(5):640-644.
[7]Cui H F,Dong K Y,Zhang G W,et al.Stereoselective construction of fluorinated indanone derivatives via a triple cascade Lewis acid-catalyzed reaction[J].Chem.Commun.,2007(22):2284-2286.
[8]王利民,盛佳,张亮,等.无溶剂条件下Yb(OTf)3催化的亚甲基化合物和醛的Knoevenagel反应[J].有机化学,2005,25(8):964-968.
[9]Yue C B,Mao A Q,Wei Y Y,et al.Knoevenagel condensation reaction catalyzed by task-specific ionic liquid under solvent-free conditions[J].Catal.Commun.,2008,9(7):1571-1574.
[10]Santamarta F,Verdia P,Tojo E.A simple,efficient and green procedure for Knoevenagel reaction in[MMIm][MSO4]ionic liquid[J].Catal.Commun.,2008,9(8):1779-1781.
[11]邵国强.离子液体中微波促进的Knoevenagel缩合反应(英文)[J].合成化学,2003,11(5):440-442.
[12]Khan F A,Dash J,Satapathy R,et al.Hydrotalcite catalysis in ionic liquid medium:a recyclable reaction system for heterogeneous Knoevenagel and nitroaldol condensation[J].TetrahedronLett.,2004,45(15):3055-3058.
[13]Rodriguez B,Bruckmann A,Bolm C.A highly efficient asymmetric organocatalytic aldol reaction in a ball mill[J].Chem.Eur.J.,2007,13(17):4710-4722.
[14]Tullberg E,Peters D,Frejd T.The Heck reaction under ball-milling conditions[J].J.Organomet.Chem.,2004,689(23):3778-3781.
[15]Zhu X Y,Li Z H,Shu Q F,et al.Mechanically activated solid-state synthesis of flavones by high-speed ball milling[J].Synth.Commun.,2009,39(23):4199-4211.
[16]Jin T S,Zhang J S,Wang A Q,et al.An efficient and environment friendly procedure for the synthesis of arylmethylenemalononitrile catalyzed by strong base anion-exchange resin in water[J].Synth.Commun.,2004,34(14):2611-2616.
[17]Rajendran A,Karthikeyan C,Rajathi K.An efficient synthesis of arylmethylidene derivatives promotedby pyridiniumsalicylateionicliquid[J].International Journal of ChemTech Research,2011,3(2):858-863.
[18]Weinberger M A,Heggie R M,Holmes H L.Solvent effects in the nuclear magnetic resonance spectra of benzalmalononitriles[J].Can.J.Chem.,1965,43(9):2585-93.
[19]Wang X S,Zeng Z S,Li Y L,et al.Simple procedure for the synthesis of arylmethylenemalononitrile without catalyst[J].Synth.Commun.,2005,35(14):1915-1920.