Acetic acid as a catalyst for the N-acylation of amines using esters as the acyl source

被引:59
|
作者
Sharley, Daniel D. Sanz [1 ]
Williams, Jonathan M. J. [1 ]
机构
[1] Univ Bath, Dept Chem, Claverton Down, Bath BA2 7AY, Avon, England
基金
英国工程与自然科学研究理事会;
关键词
NONACTIVATED CARBOXYLIC-ACIDS; DIRECT AMIDATION; AMIDE FORMATION; ACETYLATION; TRANSAMIDATION; ALCOHOLS;
D O I
10.1039/c6cc09023k
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
We report a cheap and simple method for the acetylation of a variety of amines using catalytic acetic acid and either ethyl acetate or butyl acetate as the acyl source. Catalyst loadings as low as 10 mol% afforded acetamide products in excellent yields at temperatures ranging from 80-120 degrees C. The methodology can also be successfully applied for the synthesis of a broad range of other amides, including the formation of formamides at 20 degrees C.
引用
收藏
页码:2020 / 2023
页数:4
相关论文
共 50 条
  • [21] Catalyst-Free Photooxidative N-Acylation of Azoles with Aldehydes
    Gong, Nianfeng
    Zhao, Zelin
    Young, David James
    Cao, Xiangqian
    Ren, Zhi-Gang
    Li, Hong-Xi
    CHEMISTRY-A EUROPEAN JOURNAL, 2025,
  • [22] Chemoselective N-Acylation of Amines with Acylsilanes under Aqueous Acidic Conditions
    Tian, Jing
    Li, Wei
    Deng, Xingwang
    Lakshminarayanan, Rajamani
    Srinivasan, Rajavel
    ORGANIC LETTERS, 2023, 25 (31) : 5740 - 5744
  • [23] N-acylation of sulfonamides using N-acylbenzotriazoles
    Katritzky, AR
    Hoffmann, S
    Suzuki, K
    ARKIVOC, 2004, : 14 - 22
  • [24] Cobalt(II)-Catalyzed N-Acylation of Amines through a Transamidation Reaction
    Ma, Juan
    Zhang, Feng
    Zhang, Jingyu
    Gong, Hang
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2018, 2018 (35) : 4940 - 4948
  • [25] Lipase-catalysed N-acylation of β2-amino esters
    Fitz, Monika
    Forro, Eniko
    Vigoczki, Edina
    Lazar, Laszlo
    Fueloep, Ferenc
    TETRAHEDRON-ASYMMETRY, 2008, 19 (09) : 1114 - 1119
  • [26] ON THE ACYLATION OF HYDROXYCARBOXYLIC AND MERCAPTOCARBOXYLIC ACID-ESTERS USING THE CARBODIIMIDE ACYLATION CATALYST METHOD
    RAO, NN
    ROTH, HJ
    ARCHIV DER PHARMAZIE, 1989, 322 (09) : 523 - 530
  • [27] Boric acid-catalyzed n-acylation of sulfoximines
    Harmata, Michael
    Garimallaprabhakaran, Aswin K.
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2009, 238
  • [28] N-ACYLATION OF AMINO-ACIDS WITH GLYCERIC ACID
    ANGRICK, M
    REWICKI, D
    MONATSHEFTE FUR CHEMIE, 1985, 116 (03): : 377 - 384
  • [29] N-ACYLATION OF GLUCOSAMINE BY 3-INDOLYLACETIC ACID
    LUKIN, OV
    VIGDORCHIK, MM
    TURCHIN, KF
    SUVOROV, NN
    ZHURNAL ORGANICHESKOI KHIMII, 1976, 12 (03): : 565 - 567
  • [30] SELECTIVE N-ACYLATION OF GENTAMICIN ANTIBIOTICS - SYNTHESIS OF 1-N-ACYL DERIVATIVES
    WRIGHT, JJ
    COOPER, A
    DANIELS, PJL
    NAGABHUSHAN, TL
    RANE, D
    TURNER, WN
    WEINSTEIN, J
    JOURNAL OF ANTIBIOTICS, 1976, 29 (07): : 714 - 719