NH4I-promoted N-acylation of amines via the transamidation of DMF and DMA under metal-free conditions

被引:23
作者
Chen, Jiahui [1 ]
Jia, Jing [1 ]
Guo, Ziyi [1 ]
Zhang, Jitan [1 ]
Xie, Meihua [1 ]
机构
[1] Anhui Normal Univ, Coll Chem & Mat Sci, Key Lab Funct Mol Solids, Anhui Key Lab Mol Based Mat,Minist Educ, Wuhu 241002, Peoples R China
基金
中国国家自然科学基金;
关键词
Transamidation; Amines; N-Acylation; NH4I; CARBOXYLIC-ACIDS; MAGNETIC NANOPARTICLES; FORMYLATION; AMIDES; AMIDATION; CATALYST; N; N-DIMETHYLFORMAMIDE; CARBOXAMIDES; ACCESS;
D O I
10.1016/j.tetlet.2019.04.040
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
An unprecedented NH4I-promoted N-formylation and N-acetylization of various amines with dimethylformamide (DMF) and dimethylacetamide (DMA) has been developed. This protocol shows broad substrate scope for aromatic, aliphatic, and heterocyclic amines, which provides a metal-free strategy for N-acylation featuring mild reaction conditions, as well as inexpensive and readily available starting materials. (C) 2019 Elsevier Ltd. All rights reserved.
引用
收藏
页码:1426 / 1429
页数:4
相关论文
共 37 条
[1]   Transamidation of Primary Amides with Amines Using Hydroxylamine Hydrochloride as an Inorganic Catalyst [J].
Allen, C. Liana ;
Atkinson, Benjamin N. ;
Williams, Jonathan M. J. .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2012, 51 (06) :1383-1386
[2]   Transamidation of primary carboxamides, phthalimide, urea and thiourea with amines using Fe(OH)3@Fe3O4 magnetic nanoparticles as an efficient recyclable catalyst [J].
Arefi, Marzban ;
Heydari, Akbar .
RSC ADVANCES, 2016, 6 (29) :24684-24689
[3]   Transamidation of Carboxamides Catalyzed by Fe(III) and Water [J].
Becerra-Figueroa, Liliana ;
Ojeda-Porras, Andrea ;
Gamba-Sanchez, Diego .
JOURNAL OF ORGANIC CHEMISTRY, 2014, 79 (10) :4544-4552
[4]   Graphene oxide (GO) catalyzed transamidation of aliphatic amides: An efficient metal-free procedure [J].
Bhattacharya, Suchandra ;
Ghosh, Pranab ;
Basu, Basudeb .
TETRAHEDRON LETTERS, 2018, 59 (10) :899-903
[5]   Analysis of the reactions used for the preparation of drug candidate molecules [J].
Carey, John S. ;
Laffan, David ;
Thomson, Colin ;
Williams, Mike T. .
ORGANIC & BIOMOLECULAR CHEMISTRY, 2006, 4 (12) :2337-2347
[6]   Formyloxyacetoxyphenylmethane as an N-Formylating Reagent for Amines, Amino Acids, and Peptides [J].
Chapman, Robert S. L. ;
Lawrence, Ruth ;
Williams, Jonathan M. J. ;
Bull, Steven D. .
ORGANIC LETTERS, 2017, 19 (18) :4908-4911
[7]   Manganese-Mediated Reductive Transamidation of Tertiary Amides with Nitroarenes [J].
Cheung, Chi Wai ;
Ma, Jun-An ;
Hu, Xile .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2018, 140 (22) :6789-6792
[8]   N,N-Dimethylformamide: A Multipurpose Building Block [J].
Ding, Shengtao ;
Jiao, Ning .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2012, 51 (37) :9226-9237
[9]   Amidation and esterification of carboxylic acids with amines and phenols by N,N'-diisopropylcarbodiimide: A new approach for amide and ester bond formation in water [J].
Fattahi, Nadia ;
Ayubi, Morteza ;
Ramazani, Ali .
TETRAHEDRON, 2018, 74 (32) :4351-4356
[10]   Formylation of Amines [J].
Gerack, Ciera J. ;
McElwee-White, Lisa .
MOLECULES, 2014, 19 (06) :7689-7713