3510-25-6Relevant 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.
Transition-Metal-Free Synthesis of 1,2-diphenyl-1H-benzo[d] Imidazole Derivatives from N-phenylbenzimidamides and Cyclohexanones
Lu, Guoqiang,Luo, Nan,Hu, Fangpeng,Ban, Zihui,Zhan, Zhenzhen,Huang, Guo-Sheng
supporting information, p. 487 - 492 (2019/12/12)
A transition-metal-free strategy for the formation of 1,2-diphenyl-1H-benzo[d] imidazoles from N-phenylbenzimidamides and cyclohexanones is introduced. This is the first report on the direct synthesis of 1,2-diphenyl-1H-benzo[d] imidazoles from cyclohexanones and N-phenylbenzimidamides via iodine- promoted oxidative cyclization. Non-aromatic cyclohexanones were smoothly dehydrogenated, and acted as an aryl source using oxygen as a green oxidant. The catalytic use of iodine makes this method quite simple, more economical and convenient. Under optimized conditions, various substituted 1,2-diphenyl-1H-benzo[d] imidazoles were smoothly reacted, and the desired substituted imidazoles were generated with moderate to excellent yields. (Figure presented.).
A one-pot synthesis of 1, 2 - diaryl benzimidazole and its derivatives
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Paragraph 0177; 0178; 0179; 0180; 0181; 0182; 0183, (2017/08/25)
The invention discloses a one-pot synthesis method of 1,2-diarylbenzimidazole and derivatives thereof and belongs to the technical field of chemical preparation. The synthesis method comprises the following steps: adding o-phenylenediamine, benzaldehyde and halogeno benzene which are raw materials into a pressure bottle of 50mL according to the ratio of 1:1.2:1, adding a metal catalyst, an alkali, a ligand and an organic solvent, stirring at the temperature of 110-130 DEG C for 16-24 hours to synthesize 1,2-diarylbenzimidazole and derivatives thereof, cooling, filtering, extracting, distilling at a reduced pressure, and carrying out chromatographic separation by using a column to obtain purified products. The one-pot synthesis method disclosed by the invention has the advantages of mild reaction condition, simple post-treatment, high product selectivity and wide substrate expansion range, and in addition, the one-pot synthesis method can be used for constructing polyaryl imidazole compounds and derivatives easily and efficiently.
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.
CuO nanoparticle-catalyzed diaminations for synthesis of benzimidazole derivatives
Yu, Dan,You, Qing,Zhang, Xinming,Tao, Guide,Zhang, Wu
, p. 695 - 698 (2016/07/19)
Copper oxide nanoparticles have been applied as an efficient catalyst for the formation of C–N bonds. They can catalyze diaminations for the regiospecific synthesis of 1,2-disubstituted benzimidazoles from 1,2-dihaloarenes and N-arylamidines. The best per
One-pot sequential synthesis of 1,2-disubstituted benzimidazoles under metal-free conditions
Roy, Priyabrata,Pramanik, Animesh
supporting information, p. 5243 - 5245 (2013/09/02)
An easy and inexpensive method has been developed to access 1,2-disubstituted benzimidazoles following a one-pot sequential coupling/reduction/cyclization process under metal-free neutral conditions.
"All-water" one-pot diverse synthesis of 1,2-disubstituted benzimidazoles: Hydrogen bond driven 'synergistic electrophile-nucleophile dual activation' by water
Kommi, Damodara N.,Jadhavar, Pradeep S.,Kumar, Dinesh,Chakraborti, Asit K.
, p. 798 - 810 (2013/04/24)
A new "all-water" tandem arylaminoarylation/arylaminoalkylation- reduction-cyclisation route is reported for one-pot diversity oriented synthesis of regiodefined 1,2-disubstituted benzimidazoles. Water plays a crucial and indispensable role through hydrogen bond driven 'synergistic electrophile-nucleophile dual activation' in the formation of N-mono-aryl/aryl alkyl/alkyl/cycloalkyl o-nitroanilines under metal and base-free conditions to replace the transition metal-based C-N bond formation (aryl amination) chemistry and underlines the origin of regiodefined installation of the diverse selection of aryl, aryl alkyl, and alkyl/cycloalkyl groups as substituents on the benzimidazole scaffold to form the 1,2-disubstituted benzimidazoles. The influence of the hydrogen bond effect of water in promoting the arylaminoarylation reaction under base and metal-free conditions has been realized through observation of inferior yields in D2O compared to that obtained in water during the reaction of o-fluoronitrobenzene with aniline separately performed in water and D2O under similar experimental conditions. Water also provides assistance in promoting the subsequent nitro reduction and in the final cyclocondensation steps. The role of water in promoting the cyclocondensation reaction through hydrogen bonds is realized by the differential product yields during the reaction of mono-N-phenyl-o- phenylenediamine with benzaldehyde performed separately in water and D 2O. The better hydrogen bond donor and hydrogen bond acceptor abilities of water compared to those of the organic solvents are the contributing/deciding factors for making the new water-assisted tandem arylaminoarylation/arylaminoalkylation-reduction-cyclisation strategy for the diversified synthesis of the regiodefined 1,2-disubstituted benzimidazoles effective in an aqueous medium, making it represent a true "all-water chemistry."
Copper-catalyzed synthesis of 1,2-disubstituted benzimidazoles from imidoyl chlorides
Yu, Hui,Zhang, Mei Shu,Cui, Li Ren
experimental part, p. 573 - 575 (2012/07/14)
A strategy for the synthesis of 1,2-disubstituted benzimidazoles has been developed and a variety of 1,2-disubstituted benzimidazoles were obtained from imidoyl chlorides and o-haloanilines via copper(I)-catalyzed reaction in moderate yields.
Regiospecific synthesis of 1, 2-disubstituted (hetero)aryl fused imidazoles with tunable fluorescent emission
Zhao, Dongbing,Hu, Junyi,Wu, Ningjie,Huang, Xiaolei,Qin, Xurong,Lan, Jingbo,You, Jingsong
, p. 6516 - 6519 (2012/02/02)
A palladium-catalyzed two or fourfold amination was established that allows regiospecific synthesis of a diversity-oriented library of 1, 2 disubstituted (hetero)aryl fused imidazoles, and provides an exceptional tool for the discovery of fluorescent scaf
Cobalt-catalyzed intramolecular C-N and C-O cross-coupling reactions: Synthesis of benzimidazoles and benzoxazoles
Saha, Prasenjit,Ali, Md Ashif,Ghosh, Pokhraj,Punniyamurthy, Tharmalingam
experimental part, p. 5692 - 5699 (2011/02/18)
Cobalt(ii)-complex catalyzes efficiently the intramolecular C-N and C-O cross-couplings of Z-N′-(2-halophenyl)-N-phenylamidines and N-(2-bromophenyl)benzamides to afford the corresponding substituted benzimidazoles and benzoxazoles in the presence of K2CO3 at moderate temperature. The protocol is general, air stable and affords the products selectively in moderate to high yield.
