77246-15-2Relevant 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.
N-Heterocyclic Carbene Copper(I) Complex Catalyzed Coupling of (Hetero)aryl Chlorides and Nitrogen Heterocycles: Highly Efficient Catalytic System
Zhang, Mengyao,Zhang, Yingying,Zhang, Huixin,Zeng, Yongfei,Liu, Guiyan
, p. 1252 - 1256 (2020/08/05)
A highly efficient catalytic system for the N-arylation reactions of (hetero)aryl chlorides and nitrogen heterocycles with a copper(I) complex containing a 1,10-phenanthroline analogue N-heterocyclic carbene (NHC) has been reported. The complex was characterized by 1H NMR and 13C NMR spectroscopy and elemental analysis, and its structure was determined by single-crystal X-ray diffraction. The NHC-copper(I) complex was employed as pre-catalyst for Ullmann type N-arylation reactions of (hetero)aryl chlorides with various azoles. A variety of hindered and functionalized azoles and (hetero)aryl chlorides were transformed in good to excellent yields.
Metal-Free One-Pot Synthesis of N,N′-Diarylamidines and N-Arylbenzimidazoles from Arenediazonium Salts, Nitriles, and Free Anilines
Youn, So Won,Lee, Eun Mi
supporting information, p. 5728 - 5731 (2016/11/17)
A highly efficient and facile metal-free, one-pot reaction has been developed to afford diversely substituted N-arylbenzimidazoles through chemoselective in situ generation of N,N′-diarylamidines from arenediazonium salts, nitriles, and free anilines. The advantages of this protocol consist of the operationally easy and simple one-pot procedure under metal-free and mild conditions, the direct use of inexpensive and commercially available chemicals, and thus, a cost-effective and greener process.
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.
N,N′-(Phenylmethylene)diacetamide analogues as economical and efficient ligands in copper-catalyzed arylation of aromatic nitrogen-containing heterocycles
Wan, Jie-Ping,Chai, Yun-Feng,Wu, Jian-Mei,Pan, Yuan-Jiang
experimental part, p. 3068 - 3072 (2009/06/28)
N,N′-(Phenylmethylene)diacetamide analogues which were simply prepared from the condensation reaction of an aldehyde with an amide or urea were found to be efficient ligands in copper-catalyzed coupling reaction of aryl halides with various azole nucleophiles. The newly developed ligand showed broad application scope in this conversion. Compounds including imidazoles, benzoimidazoles, pyrrole, indole, and benzotriazole were successfully arylated with diversified aromatic halides to give corresponding products in moderate to excellent yields. Georg Thieme Verlag Stuttgart.
