79110-04-6Relevant 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.
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.
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.
The Preparation of Some 2-Nitroacridines and Related Compounds
Rosevear, Judi,Wilshire, John F. K.
, p. 839 - 853 (2007/10/02)
The reaction of 2-fluoro-5-nitrobenzaldehyde with a wide variety of arylamines gives, in general, mixtures of the corresponding 2-arylamino-5-nitrobenzaldehydes and their related anils.Both aldehydes and anils readily underwent acid-catalysed cyclization to give the corresponding 2-nitroacridines.The effect of substituent on the rate of cyclization of these aldehydes and of some related anilino-benzaldehydes and -acetophenones has been studied in trifluoroacetic acid solution by means of 1H n.m.r. spectroscopy.A solution of 2-(N-methylanilino)-5-nitrobenzaldehydein trifluoroacetic acid appears to contain a substituted acridinium ion; treatment of this solution with alkali gave 10-methyl-2-nitroacridone. 1H n.m.r. data for a wide variety of substituted 2-nitroacridines are discussed.
