2586-34-7Relevant academic research and scientific papers
Analysis of Long-Range Through-Space Couplings via an Intramolecular Hydrogen Bond
Rae, Ian D.,Weigold, Josephine A.,Contreras, Ruben H.,Biekofsky, Rodolfo R.
, p. 836 - 840 (1993)
2-Fluorobenzamide and its N-methyl derivative show spin-spin couplings between the aromatic fluorine and the nitrogen and carbon of the amide group, which are absent in the corresponding N,N-dimethylamide.The N-methyl compound, in which there is a hydroge
Nitrate-promoted Selective C-H Fluorination of Benzamides and Benzeneacetamides
Ning, Xing-Qian,Lou, Shao-Jie,Mao, Yang-Jie,Xu, Zhen-Yuan,Xu, Dan-Qian
supporting information, p. 2445 - 2448 (2018/04/27)
A versatile and site-selective nitrate-promoted C-H bond fluorination using various weak coordinating amides as intrinsic directing groups was developed. Diverse tertiary and secondary amides underwent selective aromatic C-H bond fluorination, which featu
Nickel-catalyzed aminocarbonylation of aryl halides using carbamoylsilane as an amide source
Wen, Xue-Ping,Han, Yu-Ling,Chen, Jian-Xin
, p. 45107 - 45112 (2017/10/13)
The nickel-catalyzed aminocarbonylation of aryl halides using carbamoylsilane as an amide source is developed. The procedure can prepare both tertiary and secondary amides, and is applicable to various carbamoylsilanes and aryl halides containing differen
Potassium tert-Butoxide-Mediated Amine Acyl Exchange Reaction of N,N-Disubstituted Formamides with Aromatic Carbonyl Derivatives via Sequential C-N Bond Cleavage/Formation: An Approach to Aromatic Amides
Zhang, Ming-Zhong,Guo, Qing-Hu,Sheng, Wen-Bing,Guo, Can-Cheng
, p. 2855 - 2861 (2015/09/28)
A novel potassium tert-butoxide-mediated amine acyl exchange of N,N-disubstituted formamides with aromatic carbonyl derivatives in a sequential C-N bond cleavage/formation process leading to aromatic amides is described. This methodology tolerates a wide range of aromatic carbonyl compounds, including aromatic aldehydes, acyl chlorides, unactivated esters, and acid anhydrides. The usage of inexpensive and readily available reagents, broad substrate scope, and the simple, mild (50°C) and transition metal-free conditions make this protocol very practical. In addition, a plausible reaction mechanism is proposed on the basis of experimental observations.
Copper-catalyzed amide bond formation from formamides and carboxylic acids
Liu, Hong-Qiang,Liu, Jun,Zhang, Yang-Hui,Shao, Chang-Dong,Yu, Jing-Xun
, p. 11 - 14 (2015/01/30)
A highly efficient copper-catalyzed approach to form amide bonds from formamides and carboxylic acids was developed. This protocol shows broad substrate scopes and high yields in the presence of 1 mol% catalyst and 4.0 equiv. formamides.
An efficient route to 3-aminoindazoles and 3-amino-7-azaindazoles
Burke, Michael J.,Trantow, Brian M.
, p. 4579 - 4581 (2008/09/21)
A non-acidic procedure for the preparation of 3-aminoindazoles and 3-amino-7-azaindazoles from 2-fluoroaryl carboxylic acids is reported. The synthesis starts from readily available starting materials and uses mild and practical reaction conditions in a three-step overall procedure. Products were isolated for a number of examples, but yields varied significantly depending on electronic nature of the substituents.
INVESTIGATIONS ON N,N-DIALKYLBENZAMIDES BY NMR SPECTROSCOPY. PART IV. COMPARISON OF BARRIERS TO ROTATION ABOUT THE AMINE C-N BOND IN ORTHO-SUBSTITUTED N,N-DIMETHYL-AND N,N-DIETHYLBENZAMIDES
Gryf-Keller, Adam,Terpinski, Jacek,Zajaczkowska-Terpinska, Ewa
, p. 429 - 434 (2007/10/02)
The barriers to rotation about the amide C-N bond in a series of ortho-substituted N,N-dimethyl and N,N-diethylbenzamides have been compared.It has been stated that for most of substituents, namely CH3, Cl, Br, I and NO2, the rates of rotation in both series of compounds are identical within the accuracy of measurement (kEt/kMe ca.1).The remaining compounds (F, CN, CH3) show a higher rate of rotation in the series of diethylbenzamides (kEt/kMe ca.1,5).An exception are the OH derivatives in which the internal H-bond is present and because of that the barrier to rotation is lowered and the kEt/kMe ratio raised up to 2.3.
Investigations on N,N-Dialkylbenzamides by NMR Spectroscopy. 5 - Analysis of Static and Dynamic Proton NMR Spectra of 2-Fluoro- and 2,6-Difluoro-N,N-dimethyl- and N,N-Diethyl-benzamides
Duerst, Thomas,Gryff-Keller, Adam,Terpinski, Jacek
, p. 657 - 661 (2007/10/02)
The analysis of static and dynamic proton NMR spectra of 2-fluoro- and 2,6-difluoro-N,N-dimethyl- and N,N-diethyl-benzamides at various temperatures has been carried out.The conformations of the compounds have been deduced on the basis of long-range through-space proton-fluorine couplings.Free energies of activation of amide rotation have been determined for all compounds, and of carbonyl-ring rotation for one compound.
