Amidation Reaction of Quinoline‐3‐carboxylic Acids with Tetraalkylthiuram Disulfides under Simple Conditions: A facile Synthesis of Quinoline‐3‐carboxamides

2020 ◽  
Vol 9 (12) ◽  
pp. 2191-2195
Author(s):  
Jingyan Hu ◽  
Xiefeng Ye ◽  
Shuai Hao ◽  
Qianrui Zhao ◽  
Mingqin Zhao ◽  
...  
2021 ◽  
Vol 12 (1) ◽  
Author(s):  
Yunyun Ning ◽  
Shuaishuai Wang ◽  
Muzi Li ◽  
Jie Han ◽  
Chengjian Zhu ◽  
...  

AbstractDevelopment of catalytic amide bond-forming methods is important because they could potentially address the existing limitations of classical methods using superstoichiometric activating reagents. In this paper, we disclose an Umpolung amidation reaction of carboxylic acids with nitroarenes and nitroalkanes enabled by the triplet synergistic catalysis of FeI2, P(V)/P(III) and photoredox catalysis, which avoids the production of byproducts from stoichiometric coupling reagents. A wide range of carboxylic acids, including aliphatic, aromatic and alkenyl acids participate smoothly in such reactions, generating structurally diverse amides in good yields (86 examples, up to 97% yield). This Umpolung amidation strategy opens a method to address challenging regioselectivity issues between nucleophilic functional groups, and complements the functional group compatibility of the classical amidation protocols. The synthetic robustness of the reaction is demonstrated by late-stage modification of complex molecules and gram-scale applications.


2017 ◽  
Vol 15 (30) ◽  
pp. 6426-6432 ◽  
Author(s):  
Daan F. J. Hamstra ◽  
Danny C. Lenstra ◽  
Tjeu J. Koenders ◽  
Floris P. J. T. Rutjes ◽  
Jasmin Mecinović

In situ reduction of phosphine oxide by poly(methylhydrosiloxane) leads to efficient amidation reaction between carboxylic acids and amines.


ChemInform ◽  
2014 ◽  
Vol 45 (51) ◽  
pp. no-no
Author(s):  
Nicolai Stuhr-Hansen ◽  
Shahrokh Padrah ◽  
Kristian Stroemgaard

2014 ◽  
Vol 41 (11) ◽  
pp. 8355-8362 ◽  
Author(s):  
Pratapsinha B. Gorepatil ◽  
Yogesh D. Mane ◽  
Amarsinha B. Gorepatil ◽  
Mahadev V. Gaikwad ◽  
Vilas S. Ingle

2013 ◽  
Vol 11 (13) ◽  
pp. 2140 ◽  
Author(s):  
Chen Wang ◽  
Hai-Zhu Yu ◽  
Yao Fu ◽  
Qing-Xiang Guo

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