研究论文

TiCl4催化一锅法三组分合成β-氨基酮化合物

  • 杨德利 ,
  • 李加荣 ,
  • 孙克宁 ,
  • 路红燕 ,
  • 刘明星 ,
  • 史大昕
展开
  • 北京理工大学化工与环境学院 北京 100081

收稿日期: 2013-06-06

  修回日期: 2013-07-10

  网络出版日期: 2013-07-26

基金资助

北京理工大学基础研究基金资助项目

One-Pot Three Components Synthesis of β-Amido Ketones

  • Yang Deli ,
  • Li Jiarong ,
  • Sun Kening ,
  • Lu Hongyan ,
  • Liu Mingxing ,
  • Shi Daxin
Expand
  • School of Chemical Engineering and Environment, Beijing Institute of Technology, Beijing 100081

Received date: 2013-06-06

  Revised date: 2013-07-10

  Online published: 2013-07-26

Supported by

Project supported by the Foundation of Beijing Institute of Technology.

摘要

在酰氯辅助下、以四氯化钛为催化剂,不同的醛、酮和腈化物在室温三组分一锅合成了一系列β-氨基酮化合物. 考察了催化剂用量,反应温度和反应时间对产品收率的影响. 这种方法具有反应温和、操作简单、底物适用范围宽、产物收率高等优点.

本文引用格式

杨德利 , 李加荣 , 孙克宁 , 路红燕 , 刘明星 , 史大昕 . TiCl4催化一锅法三组分合成β-氨基酮化合物[J]. 有机化学, 2013 , 33(11) : 2341 -2348 . DOI: 10.6023/cjoc201306007

Abstract

A series of β-amido-ketones were synthesized by one-pot three components condensation of various aldehydes, ketones and nitriles in the presence of TiCl4 with the assistance of acyl chloride at room temperature. The effects of amount of catalyst, reaction temperature and reaction time on the products yields were investigated. This methodology offers several ad-vantages, such as mild reaction condition, operational simplicity, suitable for wide range of substrates, and excellent yields.

参考文献

[1] Zhu,J.; Bienayme,H.Mult-component Reactions,Wiley-VCH,Weinheim,2005.

[2] (a) Domling,A.; Ugi,I.Angew.Chem.,Int.Ed.2000,39,3168.

(b) Thomson,L.A.; Ellman,J.A.Chem.Rev.1996,96,555.

(c) Terret,N.K.; Gardner,M.; Gordon,D.M.; Kobylecki,R.J.; Steele,J.Tetrahedron 1995,51,8135.

[3] (a) Wessjohann,L.A.; Rivera,D.G.; Vercillo,O.E.Chem.Rev.2009,109,796.

(b) Hulme,C.; Gore,V.Curr.Med.Chem.2003,10,51.

(c) Nair,V.; Rajesh,C.; Vinod,A.U.; Bindu,S.; Sreekanth,A.R.; Mathan,J.S.; Balagopal,L.Acc.Chem.Res.2003,36,899.

[4] Casimir,J.R.; Turetta,C.; Ettouati,L.; Pairs,J.Tetrahedron Lett.1995,36,4797.

[5] Tiwari,A.K.; Nakamura,R.M.; Agawane,S.B.; Ali,A.Z.; Kumae,K.V.Bioorg.Med.Chem.Lett.2008,18,4130.

[6] (a) Barluenga,J.; Viado,A.; Aguilar,E.; Fustero,S.; Olano,B.J.Org.Chem.1993,58,5972.

(b) Enders,D.; Moser,M.; Geibel,G.Synthesis 2004,2040.

[7] (a) Kobinata,K.; Uramoto,M.; NishⅡ,M.; Kusakabe,H.; Nakamura,G.; Isono,K.Agric.Biol.Chem.1980,44,1709.

(b) Dähn,U.; Hagenmaier,H.; Höhne,H,; König,W.; Wolf,G.; Zähner,H.Arch.Microbiol.1976,107,143.

[8] Rajamohan-Reddy,P.; Balraju,V.; Madhavan,G.R.; Banerji,B.; Iqbal,J.Tetrahedron Lett.2003,44,353.

[9] (a) Zhang,X.; Fan,L.; Liu,J.; Yang,D.Res.Chem.Intermed.2011,37,811.

(b) Rao,I.N.; Prabhakaran,E.N.; Das,S.K.; Iqbal,J.J.Org.Chem.2003,68,4079.

[10] Dakin,H.D.; West,R.J.Biol.Chem.1928,78,745.

[11] Ren,Z.; Li,S.; Zhang,X.; Fan,L.; Zhou,G.; Yang,D.Chin.J.Org.Chem.2013,33,1047 (in Chinese).(任正红,李晟,张兴花,范莉,周光明,杨大成,有机化学,2013,33,1047.)

[12] Selvam,N.P.; Perumal,P.ARKIVOC 2009,265.

[13] Shinu,V.S,; Pramitha,P.; Bahulayan,D.Tetrahedron Lett.2011,52,3110.

[14] Yadav,J.S.; Reddy,B.V.S.; Shankar,K.S.; Premalatha,K.Org.Commun.2008,1,76.

[15] Heravi,M.M.; Behbahani,F.K.; Daraie,M.; Oskooie,H.A.Mol.Diversity 2009,13,375.

[16] Bahulayan,D.; Das,S.K.; Iqbal,J.J.Org.Chem.2003,68,5735.

[17] Maghsoodlu,M.T.; Hasssankhani,A.; Shaterian,H.R.; Habi-bi-Khorasani,S.M.; Mosaddegh,E.Tetrahedron Lett.2007,48,1729.

[18] Salama,T.A.; Elmorsy,S.S.; Khalil,A.G.M.; Ismail,M.A.Tetrahedron Lett.2007,48,6299.

[19] Maghsoodlu,M.T.; Hasssankhani,A.; Shaterian,H.R.; Habi-bi-Khorasani,S.M.; Mosaddegh,E.Tetrahedron Lett.2007,48,1729.

[20] Yakaish,T.; Rerry,G.; Lingaiah,B.P.V.; Narsaiah,B.; Rao,P.S.Synth.Commun.2005,46,1307.

[21] Shinu,V.S.; Sheeja,B.; Purushothaman,E.; Bahulayan,D.Tetrahedron Lett.2009,50,4838.

[22] Yakaish,T.; Rerry,G.; Lingaiah,B.P.V.; Narsaiah,B.; Rao,P.S.Synth.Commun.2005,46,1307.

[23] Pancy,G.; Singh,R.P.; Grag,A.; Singh,V.K.Tetrahedron Lett.2005,46,2137.

[24] Das,B.; Rerry,K.R.; Ramu,R.; Thirupayhi,P.; Ravikanth,B.Synlett 2006,1756.

[25] Ratiee,E.; Tork,F.; Joshaghani,M.Bioorg.Med.Chem.Lett.2006,16,1221.

[26] Ratiee,E.; Shahbazi,F.; Joshaghani,M.; Tork,F.J.Mol.Catal.A: Chem.2005,241,129.

[27] Heravi,M.M.; Ranjbar,L.; Derikvand,F.; Bamoharram,F.F.Catal.Commun.2007,8,289.

[28] (a) Bhatia,B.; Reddy,M.M.; Iqbal,J.J.Chem.Res.,Synop.1994,713.

[29] Khan,A.T.; Choudhury,L.H.; Parvin,T.; Ali,A.Tetrahedron Lett.2006,47,8137.

[30] Kumar,A.; Rao,M.S.; Ahmad,I.; Khungar,B.Aust.J.Chem.2009,62,322.

[31] Khan,A.T.; Parvin,T.; Choudhury,L.H.Tetrahedron 2007,63,5593.

[32] Heravi,M.M.; Zakeri,M.; Mohammadi,N.; Haghi,H.Synth.React.Inorg.Met.-Org.Chem.2012,42,178.

[33] Feifei,G.; Guangliang,Z.; Suoqin,Z.; Yueming,C.; Zhan,S.; Yaoxian,L.; Junlong,G.Tetrahedron 2007,63,3973.

[34] Shaoguang,S.; Qian,Z.; Qun,L.; Jing,K.; Yanbing,Y.; Dongwei,L.; Dewen,D.Tetrahedron Lett.2005,46,6271.

[35] (a) Yang,L.; Li,J.; Chai,H.; Lu,H.; Zhang,Q.; Shi,D.Chin.J.Chem.2013,31,443 (in Chinese).(杨留攀,李加荣,柴红新,路红燕,张奇,史大昕,有机化学,2013,31,443.)

(b) Yang,L.; Shi,D.; Chen,S.; Chai,H.; Huang,D.; Zhang,Q.; Li,J.Green Chem.2012,14,945.

[36] (a) Liu,C.; Yu,Q.; Tang,J.; Li,J.Chin.J.Org.Chem.2012,32,532 (in Chinese).(刘长娥,于琪瑶,唐健红,李加荣,有机化学,2012,32,532.)

(b) Liu,X.; Shi,D.; Tang,J.; Zhang,Q.; Li,J.Chin.J.Org.Chem.2011,31,1710 (in Chinese).(刘璇,史大昕,唐健红,张奇,李加荣,有机化学,2011,31,1710.)

(c) Li,J.; Zhang,L.; Shi,D.; Li,Q.; Wang,D.; Wang,C.; Zhang,Q.; Zhang,L.; Fan,Y.Synlett 2008,233.

(d) Tang,J.; Li,J.; Zhang,L.; Ma,S.; Shi,D.; Zhang,Q.; Yang,L.; Wang,X.; Liu,X.; Liu,C.J.Heterocycl.Chem.2012,49,533.

(e) Yang,L.; Li,J.; Chai,H.; Yuan,H.; Zhang,Q.; Shi,D.Chin.J.Org.Chem.2013,33,174 (in Chinese).(杨留攀,李加荣,柴红新,袁洪,张奇,史大昕,有机化学,2013,33,174.)

[37] Yang,D.; Shi,D.; Zhang,Q.; Chai,H.; Li,J.Acta Crystallogr.2013,E69,o633.

文章导航

/