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

来源：

CHEMICAL COMMUNICATIONS | 2017年 / 53卷 / 12期

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

页码：2020 / 2023

页数：4

共 50 条

[1] Chemoselective N-acylation of indoles using thioesters as acyl source
Du, Tianri
Wei, Xiangmu
Xu, Honghong
Zhang, Xin
Fang, Ruiru
Yuan, Zheng
Liang, Zhi
Li, Yahui
BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY, 2022, 18 : 89 - 94
[2] Plasma flow chemistry for direct N-acylation of amines by esters
Abedelnour, Elias
Ognier, Stephanie
Zhang, Mengxue
Schio, Laurent
Venier, Olivier
Cossy, Janine
Tatoulian, Michael
CHEMICAL COMMUNICATIONS, 2022, 58 (52) : 7281 - 7284
[3] N-acylation of ethanolamine using lipase: a chemoselective catalyst
Kidwai, Mazaahir
Poddar, Roona
Mothsra, Poonam
BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY, 2009, 5
[4] Mild and Useful Method for N-Acylation of Amines
Phukan, Kandarpa
Ganguly, Mausumi
Devi, Nirada
SYNTHETIC COMMUNICATIONS, 2009, 39 (15) : 2694 - 2701
[5] Mn(II)-Catalyzed N-Acylation of Amines
Ma, Juan
Zhang, Jingyu
Gong, Hang
SYNTHESIS-STUTTGART, 2019, 51 (03): : 693 - 703
[6] Reactivity of α-amino acids in the N-acylation with benzoic acid esters in aqueous dioxane
N. R. Ishkulova
L. E. Oparina
L. B. Kochetova
T. P. Kustova
N. V. Kalinina
L. V. Kuritsin
Russian Journal of General Chemistry, 2010, 80 : 964 - 967
[7] Reactivity of α-amino acids in the N-acylation with benzoic acid esters in aqueous dioxane
Ishkulova, N. R.
Oparina, L. E.
Kochetova, L. B.
Kustova, T. P.
Kalinina, N. V.
Kuritsin, L. V.
RUSSIAN JOURNAL OF GENERAL CHEMISTRY, 2010, 80 (05) : 964 - 967
[8] ACYLATION OF MERCURIZED ACETIC ACID ESTERS
LUTSENKO, IF
FOSS, VL
NESMEYAN.AN
DOKLADY AKADEMII NAUK SSSR, 1966, 169 (01): : 117 - &
[9] Thioacids Mediated Selective and Mild N-Acylation of Amines
Mali, Sachitanand M.
Bhaisare, Rupal D.
Gopi, Hosahudya N.
JOURNAL OF ORGANIC CHEMISTRY, 2013, 78 (11): : 5550 - 5555
[10] An Efficient Greener Approach for N-acylation of Amines in Water Using Benzotriazole Chemistry
Ibrahim, Tarek S.
Seliem, Israa A.
Panda, Siva S.
Al-Mahmoudy, Amany M. M.
Abdel-Samii, Zakaria K. M.
Alhakamy, Nabil A.
Asfour, Hani Z.
Elagawany, Mohamed
MOLECULES, 2020, 25 (11):

← 1 2 3 4 5 →