23592-51-0Relevant academic research and scientific papers
Divergent strategy for the chemoselective synthesis of N-Arylbenzimidazoles and N-Arylindazoles from arylamino oximes
Li, Zhen-Hua,Sun, Xiao-Meng,Qin, Jin-Jing,Tan, Zhi-Yong,Wang, Wen-Biao,Ma, Yao
, (2020/01/28)
An efficient and divergent synthesis of N-arylbenzimidazoles and N-arylindazoles from arylamino oximes based on reaction conditions selection was developed. The synthesis was approached by treating oximes with BTC and the chemoselectivity was regulated by the amount of Et3N. This switchable N–N and N–C bond formation process features mild reaction conditions, simple execution, high chemoselectivity and broad substrate scope.
2-Aminophenones, a common precursor to N-aryl isatins and acridines endowed with bioactivities
Brikci-Nigassa, Nahida Mokhtari,Bentabed-Ababsa, Ghenia,Erb, William,Chevallier, Floris,Picot, Laurent,Vitek, Lucille,Fleury, Audrey,Thiéry, Valérie,Souab, Mohamed,Robert, Thomas,Ruchaud, Sandrine,Bach, Stéphane,Roisnel, Thierry,Mongin, Florence
, p. 1785 - 1801 (2018/03/12)
Because N-arylation of isatin only worked with iodoferrocene (and in low yield), we employed N-arylation of 2-aminophenones and subsequent oxidative cyclization to access various N-arylated isatins. In the course of this work, we observed that N-arylation using 2-iodofuran, 2-iodobenzofuran and 2-iodobenzothiophene did not lead to the expected derivatives, but to (benzo)furo- and (benzo)thieno[2,3-b]quinolines. Separate cyclization was also performed under acidic conditions on 2-(arylamino)phenones in order to obtain acridines and related compounds. Most of the synthesized compounds were screened for their antiproliferative activity in A2058 melanoma cells, and against a panel of disease-relevant kinases such as mammalian CDK5/p25, PIM1, CLK1, DYRK1A, GSK3α/β Haspin and leishmanial CK1. The biological results are reported.
A process for the preparation method of the compound aromatic amines (by machine translation)
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Paragraph 0131; 0132; 0133; 0134, (2017/07/18)
The invention discloses a method for preparing aromatic amine compounds, comprising the following steps: under protection of inert gas, with the ratio of the phenolic compound amine according to mole 1:2 - 40 are mixed and dissolved in the solvent, 50 - 140 °C reaction 6 - 15 hours, corresponding to preparing polymerizable aromatic amine compound, and then after treatment to obtain a pure aromatic amine compound. Raw materials of this invention generally are easy, simple operation, substrate and wide range of application, in the absence of catalyst under catalytic conditions of the phenolic compound can be obtained by nucleophilic addition reaction of the corresponding aromatic amine compound, and is suitable for industrial production. The present invention allows the presence of water in the reaction system, can be ammonia or hydrazine hydrate as the substrate, in order to ammonium chloride as a catalyst and a cosolvent, the success of the preparation to obtain a level from phenol hydroxy aromatic primary amino compound. The invention to phenol hydroxy has better selectivity, even if the presence of halogen atoms in the substrate does not affect the occurrence of the reaction. (by machine translation)
Copper-catalyzed intramolecular oxidative C(sp3)-H amidation of 2-aminoacetophenones: Efficient synthesis of indoline-2,3-diones
Huang, Jinbo,Mao, Tingting,Zhu, Qiang
supporting information, p. 2878 - 2882 (2014/05/20)
An efficient synthesis of diverse indoline-2,3-diones from 2-aminoacetophenones through copper-catalyzed intramolecular C(sp3)-H amidation is developed. The reaction proceeds in DMSO by using O2 as the sole oxidant to provide the desired products in moderate to good yields.
Selenium-promoted intramolecular oxidative amidation of 2-(arylamino)acetophenones for the synthesis of N-arylisatins
Liu, Yong,Chen, Hui,Hu, Xiong,Zhou, Wang,Deng, Guo-Jun
supporting information, p. 4229 - 4232 (2013/07/26)
A convenient method for the synthesis of N-arylisatins from 2-(arylamino)acetophenones by using SeO2 as an oxidant is described. Various substituted N-arylisatins were selectively obtained in good to excellent yields. The reaction tolerates a wide range of functionalities. Copyright
Synthesis of N-arylindazoles and benzimidazoles from a common intermediate
Wray, Brenda C.,Stambuli, James P.
supporting information; experimental part, p. 4576 - 4579 (2010/11/20)
A variety of N-aryl-1H-indazoles and benzimidazoles were synthesized from common arylamino oximes in good to excellent yields. The product selectivity depends upon the base used in the reaction, as triethylamine promoted the formation of benzimidazoles, whereas 2-aminopyridine promoted the formation of N-arylindazoles. This method is valuable to the synthetic community because both indazoles and benzimidazoles are prevalent in pharmaceuticals.
12-Organyldibenzazocine-5,7-diones
Hellwinkel, Dieter,Ittemann, Peter
, p. 3165 - 3197 (2007/10/02)
The title compounds 10, 23 are formed in low yields on treatment of 2,2'-organylimino-bisbenzoic acid esters 8 with methyllithium, but in high yields in the intramolecular ester condensation with sodium hydride of triarylamines 12, containing o-acetyl-, a
