Cu-catalysed transamidation of unactivated aliphatic amides

被引:11
作者
Kumar, Vishal [1 ]
Dhawan, Sanjeev [1 ]
Bala, Renu [1 ]
Mohite, Sachin Balaso [1 ]
Singh, Parvesh [2 ]
Karpoormath, Rajshekhar [1 ]
机构
[1] Univ KwaZulu Natal Westville, Coll Hlth Sci, Dept Pharmaceut Chem, Discipline Pharmaceut Sci, ZA-4000 Durban, South Africa
[2] Univ KwaZulu Natal, Sch Chem & Phys, Westville Campus,Private Bag X, Durban, South Africa
基金
新加坡国家研究基金会;
关键词
CARBOXAMIDES; ACTIVATION; CLEAVAGE;
D O I
10.1039/d2ob01152b
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Direct transamidation is gaining prominence as a ground-breaking technique that generates a wide variety of amides without the requirement of acid-amine coupling or other intermediate steps. However, transamidation of unactivated aliphatic amides, on the other hand, has been a long-standing issue in comparison to transamidation of activated amides. Herein, we report a transamidation approach of an unactivated aliphatic amide using a copper catalyst and chlorotrimethylsilane as an additive. In addition, we used transamidation as a tool for selective N-C(O) cleavage and O-C(O) formation to synthesise 2-substituted benzoxazoles and benzothiazoles. The reactions were carried out without using any solvents and offered wide substitution scope.
引用
收藏
页码:6931 / 6940
页数:10
相关论文
共 55 条
[1]   Direct Transamidation Reactions: Mechanism and Recent Advances [J].
Acosta-Guzman, Paola ;
Mateus-Gomez, Alejandra ;
Gamba-Sanchez, Diego .
MOLECULES, 2018, 23 (09)
[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]   Zolpidem for the Treatment of Dystonia [J].
Badillo, Stephanie Patricia J. ;
Jamora, Roland Dominic G. .
FRONTIERS IN NEUROLOGY, 2019, 10
[4]   Switched reaction specificity in polyesterases towards amide bond hydrolysis by enzyme engineering [J].
Biundo, Antonino ;
Subagia, Raditya ;
Maurer, Michael ;
Ribitsch, Doris ;
Syren, Per-Olof ;
Guebitz, Georg M. .
RSC ADVANCES, 2019, 9 (62) :36217-36226
[5]   N-Boc-Amides in Cross-Coupling Reactions [J].
Bourne-Branchu, Yann ;
Gosmini, Corinne ;
Danoun, Gregory .
CHEMISTRY-A EUROPEAN JOURNAL, 2019, 25 (11) :2663-2674
[6]   Transamidation of Amides and Amidation of Esters by Selective N-C(O)/O-C(O) Cleavage Mediated by Air- and Moisture-Stable Half-Sandwich Nickel(II)-NHC Complexes [J].
Buchspies, Jonathan ;
Rahman, Md. Mahbubur ;
Szostak, Michal .
MOLECULES, 2021, 26 (01)
[7]   Recent Advances in the Metal-Catalyzed Activation of Amide Bonds [J].
Chaudhari, Moreshwar B. ;
Gnanaprakasam, Boopathy .
CHEMISTRY-AN ASIAN JOURNAL, 2019, 14 (01) :76-93
[8]   Transamidation for the Synthesis of Primary Amides at Room Temperature [J].
Chen, Jiajia ;
Xia, Yuanzhi ;
Lee, Sunwoo .
ORGANIC LETTERS, 2020, 22 (09) :3504-3508
[9]   PARACETAMOL AND PHENACETIN [J].
CLISSOLD, SP .
DRUGS, 1986, 32 :46-59
[10]   The environment of amide groups in protein-ligand complexes: H-bonds and beyond [J].
Cotesta, S ;
Stahl, M .
JOURNAL OF MOLECULAR MODELING, 2006, 12 (04) :436-444