Synthesis of amides directly from carboxylic acids and hydrazines

被引:1
作者
Bhardwaj, Nivedita [1 ]
Tripathi, Nancy [1 ]
Kumar, Sanjay [1 ]
Jain, Shreyans K. [1 ]
机构
[1] Banaras Hindu Univ, Indian Inst Technol, Dept Pharmaceut Engn & Technol, Varanasi 221005, Uttar Pradesh, India
关键词
CATALYZED AMIDATION; AMINES; ALDEHYDES; ALCOHOLS; CARBENE; CHEMISTRY; PEPTIDES;
D O I
10.1039/d3ob01268a
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The method for amide bond synthesis described here utilizes carboxylic acids and hydrazines in the presence of a catalytic amount of ZnCl2. This is the first report that highlights the use of hydrazine as an amine partner for amide synthesis directly with carboxylic acids. Ammonia (gas) is the only by-product in this method. The methodology is simple and could help in the synthesis of peptides and natural product derivatives. Zinc chloride catalyzed amide synthesis using various aliphatic/aromatic, carboxylic acid and hydrazine derivatives.
引用
收藏
页码:7572 / 7579
页数:8
相关论文
共 37 条
[1]   Direct and waste-free amidations and cycloadditions by organocatalytic activation of carboxylic acids at room temperature [J].
Al-Zoubi, Raed M. ;
Marion, Olivier ;
Hall, Dennis G. .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2008, 47 (15) :2876-2879
[2]   Metal-catalysed approaches to amide bond formation [J].
Allen, C. Liana ;
Williams, Jonathan M. J. .
CHEMICAL SOCIETY REVIEWS, 2011, 40 (07) :3405-3415
[3]   N-heterocyclic carbene-catalyzed redox amidations of α-functionalized aldehydes with amines [J].
Bode, Jeffrey W. ;
Sohn, Stephanie S. .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2007, 129 (45) :13798-+
[4]   TRANSITION METAL-CARBENE COMPLEXES [J].
CARDIN, DJ ;
CETINKAY.B ;
LAPPERT, MF .
CHEMICAL REVIEWS, 1972, 72 (05) :545-+
[5]   Oxidative amide synthesis and N-terminal α-amino group ligation of peptides in aqueous medium [J].
Chan, Wing-Kei ;
Ho, Chi-Ming ;
Wong, Man-Kin ;
Che, Chi-Ming .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (46) :14796-14797
[6]   Highly efficient ruthenium(II) porphyrin catalyzed amidation of aldehydes [J].
Chang, Joyce Wei Wei ;
Chan, Philip Wai Hong .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2008, 47 (06) :1138-1140
[7]   Practical copper(I)-catalysed amidation of aldehydes [J].
Chang, Joyce Wei Wei ;
Ton, Thi My Uyen ;
Tania, Stefani ;
Taylor, Paul C. ;
Chan, Philip Wai Hong .
CHEMICAL COMMUNICATIONS, 2010, 46 (06) :922-924
[8]   The thermal and boron-catalysed direct amide formation reactions: mechanistically understudied yet important processes [J].
Charville, Hayley ;
Jackson, David ;
Hodges, George ;
Whiting, Andrew .
CHEMICAL COMMUNICATIONS, 2010, 46 (11) :1813-1823
[9]   Catalytic amide formation with α′-hydroxyenones as acylating reagents [J].
Chiang, Pei-Chen ;
Kim, Yoonjoo ;
Bode, Jeffrey W. .
CHEMICAL COMMUNICATIONS, 2009, (30) :4566-4568
[10]   Key green chemistry research areas - a perspective from pharmaceutical manufacturers [J].
Constable, David J. C. ;
Dunn, Peter J. ;
Hayler, John D. ;
Humphrey, Guy R. ;
Leazer, Johnnie L., Jr. ;
Linderman, Russell J. ;
Lorenz, Kurt ;
Manley, Julie ;
Pearlman, Bruce A. ;
Wells, Andrew ;
Zaks, Aleksey ;
Zhang, Tony Y. .
GREEN CHEMISTRY, 2007, 9 (05) :411-420