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

[41] Catalytic activity of magnetic Fe3O4@Diatomite earth and acetic acid for the N-acylation of sulfonamides
Ghasemi, Mohammad Hadi
Kowsari, Elaheh
Hosseini, Seyed Kiumars
TETRAHEDRON LETTERS, 2016, 57 (03) : 387 - 391
[42] ACYLATION OF PRIMARY AMINES WITH ESTERS OF DICARBOXYLIC-ACID MONOPHENYLHYDRAZIDES
GRUDZINSKA, P
ACTA POLONIAE PHARMACEUTICA, 1976, 33 (03): : 311 - 319
[43] Direct N-Acylation of Lactams, Oxazolidinones, and Imidazolidinones with Aldehydes by Shvo's Catalyst
Zhang, Jian
Hong, Soon Hyeok
ORGANIC LETTERS, 2012, 14 (17) : 4646 - 4649
[44] Reusable Bronsted Acidic Ionic Liquid Efficiently Catalyzed N-Formylation and N-Acylation of Amines
Li, Chun
Wang, Mengna
Lu, Xunhua
Zhang, Ling
Jiang, Jian
Zhang, Lin
ACS SUSTAINABLE CHEMISTRY & ENGINEERING, 2020, 8 (11): : 4353 - 4361
[45] Liquid phase acylation of amines with acetic acid over HY zeolite
Narender, N
Srinivasu, P
Kulkarni, SJ
Raghavan, KV
GREEN CHEMISTRY, 2000, 2 (03) : 104 - 105
[46] Preparation and catalytic evaluation of a palladium catalyst deposited over modified clinoptilolite (Pd@MCP) for chemoselective N-formylation and N-acylation of amines
Amirsoleimani, Mina
Khalilzadeh, Mohammad A.
Zareyee, Daryoush
JOURNAL OF MOLECULAR STRUCTURE, 2021, 1225
[47] Lipoprotein N-Acylation in Staphylococcus aureus Is Catalyzed by a Two-Component Acyl Transferase System
Gardiner, John H.
Komazin, Gloria
Matsuo, Miki
Cole, Kaitlin
Goetz, Friedrich
Meredith, Timothy C.
MBIO, 2020, 11 (04): : 1 - 18
[48] Preparation and catalytic evaluation of a palladium catalyst deposited over modified clinoptilolite (Pd@MCP) for chemoselective N-formylation and N-acylation of amines
Amirsoleimani, Mina
Khalilzadeh, Mohammad A.
Zareyee, Daryoush
Journal of Molecular Structure, 2021, 1225
[49] THE N-ACYLATION OF N-(4-METHOXYPHENYL)-4-CHLOROANTHRANILIC ACID
SARGENT, LJ
JOURNAL OF ORGANIC CHEMISTRY, 1949, 14 (02): : 285 - 288
[50] Palladium-Catalyzed N-Acylation of Tertiary Amines by Carboxylic Acids: A Method for the Synthesis of Amides
Li, Zhaohui
Liu, Long
Xu, Kaiqiang
Huang, Tianzeng
Li, Xinyi
Song, Bin
Chen, Tieqiao
ORGANIC LETTERS, 2020, 22 (14) : 5517 - 5521

← 1 2 3 4 5 →