Direct synthesis of amides from nonactivated carboxylic acids using urea as nitrogen source and Mg(NO3)2or imidazole as catalysts

被引:31
作者
Chhatwal, A. Rosie [1 ]
Lomax, Helen, V [2 ]
Blacker, B. A. John [3 ]
Williams, Jonathan M. J. [1 ]
Marce, Patricia [1 ]
机构
[1] Univ Bath, Dept Chem, Bath BA2 7AY, Avon, England
[2] Univ Bath, Ctr Sustainable Chem Technol, Bath BA2 7AY, Avon, England
[3] Univ Leeds, Sch Chem, Inst Proc Res & Dev, Woodhouse Lane, Leeds LS2 9JT, W Yorkshire, England
基金
英国工程与自然科学研究理事会;
关键词
PEPTIDE COUPLING REAGENTS; ONE-POT SYNTHESIS; OXIDATIVE AMIDATION; HIGHLY EFFICIENT; ENZYMATIC-SYNTHESIS; AQUEOUS-MEDIUM; BOND FORMATION; AMINES; ALDEHYDES; ALCOHOLS;
D O I
10.1039/d0sc01317j
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
A new method for the direct synthesis of primary and secondary amides from carboxylic acids is described using Mg(NO3)(2)center dot 6H(2)O or imidazole as a low-cost and readily available catalyst, and urea as a stable, and easy to manipulate nitrogen source. This methodology is particularly useful for the direct synthesis of primary and methyl amides avoiding the use of ammonia and methylamine gas which can be tedious to manipulate. Furthermore, the transformation does not require the employment of coupling or activating agents which are commonly required.
引用
收藏
页码:5808 / 5818
页数:11
相关论文
共 117 条
  • [1] Frontiers in catalytic nitrile hydration: Nitrile and cyanohydrin hydration catalyzed by homogeneous organometallic complexes
    Ahmed, Takiya J.
    Knapp, Spring Melody M.
    Tyler, David R.
    [J]. COORDINATION CHEMISTRY REVIEWS, 2011, 255 (7-8) : 949 - 974
  • [2] Novel Imidazolium-Based Gemini Surfactants: Synthesis, Surface Properties, Corrosion Inhibition and Biocidal Activity Against Sulfate-Reducing Bacteria
    Aiad, Ismail
    Emam, Dalia
    El-Deeb, Ali
    Abd-Alrahman, Eman
    [J]. JOURNAL OF SURFACTANTS AND DETERGENTS, 2013, 16 (06) : 927 - 935
  • [3] Mechanistic Studies into Metal-Catalyzed Aldoxime to Amide Rearrangements
    Allen, C. Liana
    Lawrence, Ruth
    Emmett, Liam
    Williams, Jonathan M. J.
    [J]. ADVANCED SYNTHESIS & CATALYSIS, 2011, 353 (18) : 3262 - 3268
  • [4] Direct amide formation from unactivated carboxylic acids and amines
    Allen, C. Liana
    Chhatwal, A. Rosie
    Williams, Jonathan M. J.
    [J]. CHEMICAL COMMUNICATIONS, 2012, 48 (05) : 666 - 668
  • [5] Metal-catalysed approaches to amide bond formation
    Allen, C. Liana
    Williams, Jonathan M. J.
    [J]. CHEMICAL SOCIETY REVIEWS, 2011, 40 (07) : 3405 - 3415
  • [6] Catalytic Acylation of Amines with Aldehydes or Aldoximes
    Allen, C. Liana
    Davulcu, Simge
    Williams, Jonathan M. J.
    [J]. ORGANIC LETTERS, 2010, 12 (22) : 5096 - 5099
  • [7] Cost efficient synthesis of amides from oximes with indium or zinc catalysts
    Allen, C. Liana
    Burel, Celine
    Williams, Jonathan M. J.
    [J]. TETRAHEDRON LETTERS, 2010, 51 (20) : 2724 - 2726
  • [8] An iron-catalysed synthesis of amides from nitriles and amines
    Allen, C. Liana
    Lapkin, Alexei A.
    Williams, Jonathan M. J.
    [J]. TETRAHEDRON LETTERS, 2009, 50 (29) : 4262 - 4264
  • [9] [Anonymous], U. S. Pat, Patent No. [2109941A, 2109941]
  • [10] A mild and efficient procedure for the conversion of aromatic carboxylic esters to secondary amides
    Arora, R
    Paul, S
    Gupta, R
    [J]. CANADIAN JOURNAL OF CHEMISTRY, 2005, 83 (08) : 1137 - 1140