68874-08-8Relevant 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.
Base-assisted, copper-catalyzed N-arylation of (benz)imidazoles and amines with diarylborinic acids
Guan, Changwei,Feng, Yuanyuan,Zou, Gang,Tang, Jie
, p. 6906 - 6913 (2017/11/03)
N-Arylation of (benz)imidazoles and amines with diarylborinic acids as cost-effective aryl source has been efficiently effected via Cu(OAc)2-catalyzed Chan-Lam coupling in assistance of tetramethylethylenediamine (TMEDA) in methanol and pyridine (Py) in dichloromethane, respectively, in air at room temperature. The diarylborinic acids could be well accommodated by the Chan-Lam coupling oxidative conditions containing a proper combination of bases and solvents. The steric hindrance appeared to affect the copper-catalyzed N-arylation using the high-order arylboron reagent more significantly than the electronic factors, especially for low reactive anilines and aliphatic amines.
DAST-promoted Beckmann rearrangement/intramolecular cyclization of acyclic ketoximes: Access to 2-oxazolines, benzimidazoles and benzoxazoles
Li, Huiqin,Qin, Jian,Yang, Zonglian,Guan, Xiaoxue,Zhang, Lin,Liao, Peiqiu,Li, Xingqi
supporting information, p. 8637 - 8639 (2015/05/20)
The first example of DAST-promoted Beckmann rearrangement/intramolecular cyclization of acyclic ketoximes is described. This unique protocol represents a direct and effective pathway to 2-oxazolines, benzimidazoles and benzoxazoles 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.
Copper-catalyzed synthesis of benzimidazoles via cascade reactions of o-haloacetanilide derivatives with amidine hydrochlorides
Yang, Daoshan,Fu, Hua,Hu, Liming,Jiang, Yuyang,Zhao, Yufen
, p. 7841 - 7844 (2008/12/22)
(Chemical Equation Presented) We have developed an efficient method for the synthesis of benzimidazoles via cascade reactions of o-haloacetoanilide derivatives with amidine hydrochlorides. The protocol uses 10 mol % CuBr as the catalyst, CS2CO
A palladium-catalyzed regiospecific synthesis of N-aryl benzimidazoles
Zheng, Nan,Anderson, Kevin W.,Huang, Xiaohua,Nguyen, Hanh Nho,Buchwald, Stephen L.
, p. 7509 - 7512 (2008/09/17)
(Chemical Equation Presented) Highly tolerated: A catalytic method employing [Pd2(dba)3] and XPhos or RuPhos permits the efficient synthesis of N-aryl benzimidazoles in regioisomerically pure form starting from ortho-halo-anilides (see scheme), and tolerates a wide range of functional groups, dba = trans,trans-dibenzylideneacetone.
Synthesis of 1,2-Disubstituted Benzimidazoles by the Photolysis of Imidoylbenzotriazoles
Katritzky, Alan R.,Yang, Baozhen,Abonia, Rodrigo,Insuasty, Braulio
, p. 540 - 541 (2007/10/03)
A novel synthesis of 1,2-disubstituted benzimidazoles based on photolysis of imidoylbenzotriazoles is described.
