41214-79-3Relevant academic research and scientific papers
Transition-metal-free mono- or dinitration of protected anilines
Dai, Enrui,Dong, Ying,Dong, Yongrui,Kong, Rui,Liang, Deqiang,Liu, Guangzhang,Ma, Yinhai,Wu, Qiong
, (2020/04/27)
An amide-assisted arene nitration is presented, and both mono- and dinitration of protected anilines could be effected by using NaNO2 and NaNO3 as the mono- and bisnitrating agents, respectively. This divergent synthesis is transition-metal- and acid-free, and features a broad substrate scope, low cost, and ortho–para selectivity.
Reversible small molecule inhibitors of MAO A and MAO B with anilide motifs
Grau, Kathrin,Hagenow, Jens,Hagenow, Stefanie,Hefke, Lena,Khanfar, Mohammad,Proschak, Ewgenij,Stark, Holger
, p. 371 - 393 (2020/02/11)
Background: Ligands consisting of two aryl moieties connected via a short spacer were shown to be potent inhibitors of monoamine oxidases (MAO) A and B, which are known as suitable targets in treatment of neurological diseases. Based on this general blueprint, we synthesized a series of 66 small aromatic amide derivatives as novel MAO A/B inhibitors. Methods: The compounds were synthesized, purified and structurally confirmed by spectroscopic methods. Fluorimetric enzymological assays were performed to determine MAO A/B inhibition properties. Mode and reversibility of inhibition was determined for the most potent MAO B inhibitor. Docking poses and pharmacophore models were generated to confirm the in vitro results. Results: N-(2,4-Dinitrophenyl)benzo[d][1,3]dioxole-5-carboxamide (55, ST-2043) was found to be a reversible competitive moderately selective MAO B inhibitor (IC50 = 56 nM, Ki = 6.3 nM), while N-(2,4-dinitrophenyl)benzamide (7, ST-2023) showed higher preference for MAO A (IC50 = 126 nM). Computational analysis confirmed in vitro binding properties, where the anilides examined possessed high surface complementarity to MAO A/B active sites. Conclusion: The small molecule anilides with different substitution patterns were identified as potent MAO A/B inhibitors, which were active in nanomolar concentrations ranges. These small and easily accessible molecules are promising motifs, especially for newly designed multitargeted ligands taking advantage of these fragments.
CuSO4-mediated decarboxylative C-N cross-coupling of aromatic carboxylic acids with amides and anilines
Sheng, Wei-Jian,Ye, Qing,Yu, Wu-Bin,Liu, Ren-Rong,Xu, Meng,Gao, Jian-Rong,Jia, Yi-Xia
supporting information, p. 599 - 601 (2015/02/19)
CuSO4-mediated decarboxylative C-N cross-coupling of aromatic carboxylic acid with amide has been developed, leading to N-arylamides in modest to excellent yields. Anilines bearing electron-withdrawing substituents could also couple efficiently
Oxidative arylamination of 1,3-dinitrobenzene and 3-nitropyridine under anaerobic conditions: The dual role of the nitroarenes
Gulevskaya, Anna V.,Tyaglivaya, Inna N.,Verbeeck, Stefan,Maes, Bert U.W.,Tkachuk, Anna V.
experimental part, p. 238 - 251 (2011/08/22)
1,3-Dinitrobenzene and 3-nitropyridine react with lithium arylamides under anaerobic conditions to produce N-aryl-2,4-dinitroanilines and N-aryl-5-nitropyridin-2-amines, respectively, in 8-42% yields. ARKAT-USA, Inc.
Colorimetric detection of cyanide with N-nitrophenyl benzamide derivatives
Sun, Yue,Wang, Guofeng,Guo, Wei
experimental part, p. 3480 - 3485 (2009/08/15)
A series of structurally simple N-nitrophenyl benzamide derivatives have been developed as chemosensors toward cyanide in aqueous environment by taking advantage of the cyanide's strong affinity toward the acyl carbonyl carbon. The high selectivity of these compounds toward CN- makes it a practical system for monitoring CN- concentrations in aqueous samples.
Direct coupling of nucleophiles with nitroaromatic compounds via fluoride-promoted oxidative nucleophilic aromatic substitution for hydrogen
Huertas, Inma,Gallardo, Iluminada,Marquet, Jordi
, p. 3439 - 3441 (2007/10/03)
Useful yields are achieved in the regioselective direct coupling of amines, amides, and ketones with m-dinitrobenzene, 1-nitronaphthalene, and 1,3-dinitronaphthalene, through oxidatively activated nucleophilic aromatic substitution for hydrogen promoted by fluoride anions.
Ammonium nickel sulphate mediated nitration of aromatic compounds with nitric acid
Tasneem,Ali,Rajanna,Saiparakash
, p. 1123 - 1127 (2007/10/03)
Aromatic compounds were efficiently nitrated under mild conditions employing ammonium nickel sulphate and nitric acid as a reagent. This procedure works efficiently at room temperature yielding mononitro derivative in fair to good yield with high regioselectivity.
Direct formation of aromatic C-N bonds. Regioselective amination of m- dinitrobenzene via fluoride promoted nucleophilic aromatic photosubstitution for hydrogen
Huertas, Inma,Gallardo, Iluminada,Marquet, Jordi
, p. 279 - 281 (2007/10/03)
Useful yields are achieved in the regioselective direct formation of anilines and aromatic amides through hydrogen nucleophilic aromatic photosubstitution of m-dinitrobenzene with primary amines and amides, promoted by fluoride anion.
Mild, efficient and selective nitration of anilides, non-activated and moderately activated aromatic compounds with ammonium molybdate and nitric acid as a new nitrating agent
Sana, Sariah,Rajanna,Ali, Mir Moazzam,Saiprakash
, p. 48 - 49 (2007/10/03)
Ammonium molybdate [Mo(VI)] is operationally simple, environmentally safe and inexpensive reagent. Regioselective nitration of anilides, non-activated and moderately activated aromatic compounds could be afforded by employing ammonium molybdate and nitric acid as mild and effective nitrating agent. This procedure works efficiently under reflux conditions to prepare mononitroderivatives of anilides, non-activated and moderately activated aromatic compounds in good to excellent yield with high regioselectivity.
N-Acyltetrazole as an intermediate for preparation of carboxylic acid derivatives
Jursic
, p. 361 - 364 (2007/10/02)
A new mild and very efficient procedure for preparation of acid derivatives via N-acyl-5-phenyltetrazole is reported. The yields are high at -10°C and purification is simple but, because of the thermal instability of the intermediate, a certain amount of corresponding oxadiazole arises if the reaction is carried out at higher temperature.
