三组分一锅法合成2-芳基-苯并三唑基甲基-β-酮酸酯衍生物
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摘要
为了用一锅法合成2-芳基-苯并三唑基甲基-β-酮酸酯衍生物,开发了一种以CeCl_3·7H_2O催化,芳香醛、苯并三唑和1,3-二羰基化合物三组分一锅法的新方法.结果表明:该方法具有收率良好、操作简便、条件温和、官能团兼容性好等优点.三组分一锅法合成2-芳基-苯并三唑基甲基-β-酮酸酯衍生物的方法符合绿色化学的发展趋势.
In order to obtain one-pot synthesis of 2-aryl-benzotrizolyl-methyl-β-ketoacid ester derivatives, a new method was developed with CeCl_3·7 H_2O as the catalyst starting from readily available aromatic alhehydes, benzotrizole and 1,3-dicarbonyl compounds. The method had the advantages of good yield, simple operation, high efficiency and good functional group tolerance. Especially, the three component one-pot reaction made the method in line with the trend of green chemistry.
In order to obtain one-pot synthesis of 2-aryl-benzotrizolyl-methyl-β-ketoacid ester derivatives, a new method was developed with CeCl_3·7 H_2O as the catalyst starting from readily available aromatic alhehydes, benzotrizole and 1,3-dicarbonyl compounds. The method had the advantages of good yield, simple operation, high efficiency and good functional group tolerance. Especially, the three component one-pot reaction made the method in line with the trend of green chemistry.
引文
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[2]KATRITZKY A R,LAN X,YANG J Z,et al.Properties and synthetic utility of N-substituted benzotriazoles[J].Chem Rev,1998,98(2):409-548.
[3]KATRITZKY A R,YANG Z,CUNDY D J.Benzotriazole-stabilized carbanions:Generation,reactivity,and synthetic utility[J].Aldrichimiea Acta,1994,27(2):31-38.
[4]AL-SOUD Y A,AL-MASOUDI N A,FERWANAH A R.Synthesis and properties of new substituted 1,2,4-triazoles:Potential antitumor agents[J].Bioorg Med Chem,2003,11(8):1701-1708.
[5]KATARZYNA K Z,ANDZELIKA N,JUSTYNA Z,et al.Synthesis and activity of 1H-benzimidazole and 1H-benzotriazole derivatives as inhibitors of acanthamoeba castellanii[J].Bioorg Med Chem,2004,12(10):2617-2624.
[6]HANDRATTA V D,VASAITIS T S,NJAR V C O,et al.Novel C-17-heteroaryl steroidal CYP17 inhibitors/antiandrogens:Synthesis,in vitro biological activity,pharmacokinetics,and antitumor activity in the LAPC4 human prostate cancer xenograft model[J].J Med Chem,2005,48(8):2972-2984.
[7]LI W X,YE Y,ZHANG J,et al.Dy(OTf)3-mediated selective substitution of N-(α-benzotriazolyl-alkyl)amides with active methylene compounds for synthesis of benzotriazole derivatives[J].Tetrahedron Lett,2009,50(39):5536-5538.
[8]ZHOU L J,LV X,MAO H,et al.Selective substitution reactions of methoxycarbonylamino-1-(1-benzotriazolyl)alkanes with active methylene compounds[J].J Heterocyclic Chem,2011,48(2):434-440.
[9]KATRITZKY A R,KIRIEHENKO K,ELSAYED A M,et al.Convenient preparation of tert butyl β-(protected amino)esters[J].J Org Chem,2002,67(14):4957-4959.
[10]KATRITZKY A R,XIE L H,FAN W Q.Convenient novel syntheses of 1,l-bis(heteroary1)alkanes[J].J Org Chem,1993,58(16):4376-4381.
[11]SHETTY K S M,SOMASHEKAR V,MOHAN S.Microwave induced synthesis and biological evaluation of some schiff bases of 2-amino-3-(N-chlorophenyl carboxamido)-4,5-dimethyl thiophenes[J].Asian J Chem,2004,16(2):623-627.
[12]MAO H,WAN J P,PAN Y J.Facile and diastereoselective synthesis of β-acetamido ketones and keto esters via direct Mannich-type reaction[J].Tetrahedron,2009,65(5):1026-1032.
[13]DAI Y,LI B D,QUAN H D,et al.CeCl3·7H2O as an efficient catalyst for one-pot synthesis of β-amino ketones by three-component Mannich reaction[J].Chinese Chem Lett,2010,21(1):31-34.