欢迎登录材料期刊网

材料期刊网

高级检索

The multicomponent condensation of an aryl aldehyde,acetyl chloride,acetonitrile,and enolizable ketone as one-pot synthesis of β-acetamido ketones in high yields was investigated using commercial,non-corrosive,and environmentally benign Keggin and Wells-Dawson heteropolyacid catalysts.The best catalyst was H5PW10V2O40.The methodology used simple experimental conditions,and the short reaction times and high yields indicate it is a useful strategy for the large scale synthesis of β-acetamido ketones.

参考文献

[1] Casimir JR.;Ettouati L.;Paris J.;Turetta C. .FIRST APPLICATION OF THE DAKIN-WEST REACTION TO FMOC CHEMISTRY - SYNTHESIS OF THE KETOMETHYLENE TRIPEPTIDE FMOC-N-ALPHA-ASP(TBU)-(R,S)TYR(TBU)PSI(CO-CH2)GLY-OH[J].Tetrahedron letters: The International Journal for the Rapid Publication of Preliminary Communications in Organic Chemistry,1995(27):4797-4800.
[2] Godfrey AG.;Brooks DA.;Hay LA.;Peters M.;McCarthy JR.;Mitchell D. .Application of the Dakin-West reaction for the synthesis of oxazole-containing dual PPAR alpha/gamma agonists[J].The Journal of Organic Chemistry,2003(7):2623-2632.
[3] Dahn U;Hagenmaier H;Hohne H;Konig W A Wolf G Zahner H .[J].Archives of Microbiology,1976,107:143.
[4] Kobinata K;Uramoto M;Nishii M;Kusakabe H Nakamura G Isono K .[J].Agricultural and Biological Chemistry,1980,44:1709.
[5] Dakin H D;West R .[J].Journal of Biological Chemistry,1982,78:745.
[6] Buchanan G L .[J].Chem SocRev,1988,17:91.
[7] Bhatia B;Reddy M M;Iqbal J.[J].Journal of the Chemical Society,Chemical Communications,1994:713.
[8] Weber L .The application of multi-component reactions in drug discovery.[J].Current medicinal chemistry,2002(23):2085-2093.
[9] Strubing D;Neumann H;Klaus S;Hubner S;Beller M .A facile and efficient synthesis of enyne-reaction precursors by multicomponent reactions[J].Tetrahedron,2005(48):11333-11344.
[10] Heydari A;Arefi A;Khaksar S;Shiroodi R K .[J].Journal of Molecular Catalysis A:Chemical,2007,271:142.
[11] Guillena G;Ramon D J;Yus M .[J].Tetrahedron:Asymmetry,2007,18:693.
[12] Hulme C.;Tang SY.;Burns CJ.;Morize I.;Labaudiniere R.;Peng J. .Improved procedure for the solution phase preparation of 1,4-benzodiazepine-2,5-dione libraries via Armstrong's convertible isonitrile and the Ugi reaction[J].The Journal of Organic Chemistry,1998(22):8021-8023.
[13] Hulme C;Ma L;Romano J;Morrissette M .[J].Tetrahedron Letters,1999,40:7925.
[14] Zhu J;Bienayme H.Multicomponent Reactions[M].Weinheim:Wiley,2005
[15] Mukhopadhyay M;Bhatia B;Iqbal J .[J].Tetrahedron Letters,1997,38:1083.
[16] Bahulayan D.;Das SK.;Iqbal J. .Montmorillonite K10 clay: An efficient catalyst for the one-pot stereoselective synthesis of beta-acetanxido ketones[J].The Journal of Organic Chemistry,2003(14):5735-5738.
[17] Ghosh R;Maiti S;Chakraborty A .One-pot multicomponent synthesis of p-acetamido ketones based on BiCl3 generated in situ from the procatalyst BiOCl and acetyl chloride[J].Synlett,2005(1):115-118.
[18] Khodaei M M;Khosropour A R;Fattahpour P .[J].Tetrahedron Letters,2005,46:2105.
[19] Pandey G;Singh R P;Garg A;Singh V K .[J].Tetrahedron Letters,2005,46:2137.
[20] Rafiee E;Tork F;Joshaghani M .Heteropoly acids as solid green Bronsted acids for a one-pot synthesis of beta-acetamido ketones by Dakin-West reaction.[J].Bioorganic and Medicinal Chemistry Letters,2006(5):1221-1226.
[21] Bhat R P;Raje V P;Alexander V M;Patil S B Samant S D .[J].Tetrahedron Letters,2005,46:4801.
[22] Singh R;Kissling R M;Letellier M A;Nolan S P .[J].Journal of Organic Chemistry,2004,69:209.
[23] Anastas P T;Bartlett L B;Kirchhoff M M;Williamson T C .[J].Catalysis Today,2000,55:11.
[24] Tsigdinos G A;Hallada C J .[J].Inorganic Chemistry,1968,7:437.
[25] Rezaei-Seresht E;Zonoz M F;Estiri M;Tayebee R .[J].Industrial and Engineering Chemistry Research,2011,50:1837.
[26] Farhadi S;Taherimehr M .[J].ACTA CHIMICA SLOVENICA,2008,55:637.
[27] Cadot E;Thouvenot R;Teze A;Herve G .[J].Inorganic Chemistry,1992,31:4128.
[28] Alizadeh M H;Harmalker S P;Jeanin Y;Martin-Frere J Pope M T .[J].Journal of the American Chemical Society,1985,107:2662.
[29] Rao IN.;Prabhakaran EN.;Das SK.;Iqbal J. .Cobalt-catalyzed one-pot three-component coupling route to beta-acetamido carbonyl compounds: A general synthetic protocol for gamma-lactams[J].The Journal of Organic Chemistry,2003(10):4079-4082.
[30] Mizuno N.;Misono M. .Heterogenous catalysis [Review][J].Chemical Reviews,1998(1):199-217.
[31] Marchal-Roch C;Millet J M M .[J].Acad Sci Paris S(e)r Chim,2001,4:321.
[32] Marchal-Roach C;Laronze N;Guillou N;Teze A Herve G .[J].Applied Catalysis A:General,2000,199:33.
[33] Pope M T.Heteropoly and Isopoly Oxometalates[M].Beilin:Springer-Verlag,1983
[34] Casarini D;Centi G;Jiru P;Lena V Tvaruzkova Z .[J].Journal of Catalysis,1993,143:325.
[35] Rocchiccioli-Deltcheff C;Fournier M;J Chem Soc .[J].Journal of the Chemical Society,Faraday Transactions,1991,87:3913.
[36] Davoodnia A;Heravi M M;Rezaei-Daghigh L;Tavakoli-Hoseini N .[J].Monat Chem,2009,140:1499.
[37] Ghosh R;Maiti S;Chakraborty A;Chakraborty S;Mukherjee AK .ZrOCl2 center dot 8H(2)O: an efficient Lewis acid catalyst for the one-pot multicomponent synthesis of beta-acetamido ketones[J].Tetrahedron,2006(17):4059-4064.
[38] Mirjalili B B F;Hashemi M M;Sadeghi B;Emtiazi H .[J].Journal of the Chinese Ceramic Society,2009,56:386.
[39] Rafiee E;Shahbazi F;Joshaghani M;Tork F .[J].Journal of Molecular Catalysis A:Chemical,2005,242:129.
[40] Khan A T;Parvin T;Choudhury L H .[J].Tetrahedron,2007,63:5593.
[41] Siddaiah V;Damu G L V;Sudhakar D;Venkata Rao C Christopher V .[J].Journal of The Korean Chemical Society,2008,52:712.
[42] Yakaiah T;Lingaiah B P V;Reddy G V;Narsaiah B,Rao P S.[J].Arkivoc,2007:227.
上一张 下一张
上一张 下一张
计量
  • 下载量()
  • 访问量()
文章评分
  • 您的评分:
  • 1
    0%
  • 2
    0%
  • 3
    0%
  • 4
    0%
  • 5
    0%