23275-60-7Relevant academic research and scientific papers
Copper Acetate Aerobic Oxidative Synthesis of Pyrido[1,2- a ]benzimidazoles from Aminopyridines and Phenylboronic Acids
Guo, Hui,Liu, Jingli,Yan, Hao,Zhang, Guanghui,Zhang, Shuan,Zhou, Xiaoqiang,Zuo, Zhenyu
, p. 1469 - 1473 (2019)
Pyrido[1,2- a ]benzimidazoles, which show interesting and potentially useful biological activities, have drawn extensive attention from chemists. A straightforward copper acetate-oxidative one-pot synthesis of these compounds from 2-aminopyridines and phenylboronic acids through C-N bond formation and C-H bond activation was developed as a simple and convenient method.
Tunable Electrochemical C?N versus N?N Bond Formation of Nitrogen-Centered Radicals Enabled by Dehydrogenative Dearomatization: Biological Applications
Chen, Jianbin,Cui, Yuezhi,Gao, Wei,Han, Xiaoxin,Hu, Wei,Lv, Shide,Ma, Li,Niu, Liwei,Wang, Jian-Yong,Wu, Yanwei,Zhou, Jianhua,Zhou, Mingyang
supporting information, p. 11583 - 11590 (2020/05/06)
Herein, an environmentally friendly electrochemical approach is reported that takes advantage of the captodative effect and delocalization effect to generate nitrogen-centered radicals (NCRs). By changing the reaction parameters of the electrode material and feedstock solubility, dearomatization enabled a selective dehydrogenative C?N versus N?N bond formation reaction. Hence, pyrido[1,2-a]benzimidazole and tetraarylhydrazine frameworks were prepared through a sustainable transition-metal- and exogenous oxidant-free strategy with broad generality. Bioactivity assays demonstrated that pyrido[1,2-a]benzimidazoles displayed antimicrobial activity and cytotoxicity against human cancer cells. Compound 21 exhibited good photochemical properties with a large Stokes shift (approximately 130 nm) and was successfully applied to subcellular imaging. A preliminary mechanism investigation and density functional theory (DFT) calculations revealed the possible reaction pathway.
Efficient pyrido[1,2-a]benzimidazole formation from 2-aminopyridines and cyclohexanones under metal-free conditions
Xie, Yanjun,Wu, Jun,Che, Xingzong,Chen, Ya,Huang, Huawen,Deng, Guo-Jun
supporting information, p. 667 - 671 (2016/02/12)
An efficient procedure for pyrido[1,2-a]benzimidazole preparation from 2-aminopyridines and cyclohexanones under metal-free conditions is described. Non-aromatic cyclohexanones were used as the aryl source via a dehydrogenation-aromatization process using molecular oxygen as the green oxidant.
C-H cycloamination of N-aryl-2-aminopyridines and N-arylamidines catalyzed by an in situ generated hypervalent iodine(iii) reagent
He, Yimiao,Huang, Jinbo,Liang, Dongdong,Liu, Lanying,Zhu, Qiang
, p. 7352 - 7354 (2013/09/23)
A metal-free synthesis of diversified pyrido[1,2-a]benzimidazoles and 1H-benzo[d]imidazoles from N-aryl-2-aminopyridines and N-arylamidines has been developed. The C-H cycloamination reaction was catalyzed by hypervalent iodine(iii) species generated in situ from iodobenzene (catalytic) and peracetic acid (stoichiometric). The reaction proceeded smoothly at ambient temperature to provide the corresponding N-heterocycles in good to excellent yields.
A metal-free tandem demethylenation/C(sp2)-H cycloamination process of N -Benzyl-2-aminopyridines via C-C and C-N bond cleavage
Liang, Dongdong,He, Yimiao,Liu, Lanying,Zhu, Qiang
, p. 3476 - 3479 (2013/07/26)
A mild, metal-free synthesis of pyrido[1,2-a]benzimidazoles starting with N-benzyl-2-aminopyridines, which employs PhI(OPiv)2 as a stoichiometric oxidant, has been developed. The process is initiated by an unusual PhI(OPiv)2-mediated ipso SEAr reaction, followed by solvent-assisted C-C and C-N bond cleavage.
Synthesis of pyrido[1,2-a]benzimidazoles by photo-stimulated C-N bond formation via SRN1 reactions
Barolo, Silvia M.,Wang, You,Rossi, Roberto A.,Cuny, Gregory D.
, p. 5487 - 5494 (2013/06/27)
The photo-stimulated cyclization of 2-(2-halophenylamino)pyridines in liquid ammonia afforded pyrido[1,2-a]benzimidazoles via SRN1 mediated C-N bond forming reactions in moderate to excellent yields (58-94%). This general synthetic strategy was also extended to a 2-(2-bromophenylamino)pyrazine to give pyrazino[1,2-a]benzimidazole. Attempts to employ this reaction using N-(2-chlorophenyl)-3-isoquinolinamine, however, resulted in C-C bond formation generating 7H-indolo[2,3-c]isoquinoline.
Facile synthesis of pyrido[1,2-a]benzimidazole derivatives via novel tandem reaction involving horner-emmons reaction
Zhao, Wen-Jing,Xie, Ya-Fei,Ge, Yan-Qing,Xu, Wei-Ren,Zhao, Gui-Long,Wang, Jian-Wu
, p. 1121 - 1126 (2013/05/23)
Pyrido[1,2-a]benzimidazole derivatives were conveniently synthesized by a novel tandem reaction under mild conditions. The reaction mechanism was also proposed.
Synthesis of pyrido[1,2-a]benzimidazoles through a copper-catalyzed cascade C-N coupling process
Wu, Zhiqing,Huang, Qing,Zhou, Xiangge,Yu, Lintao,Li, Zhengkai,Wu, Di
supporting information; experimental part, p. 5242 - 5245 (2011/11/13)
A simple and efficient method for the preparation ofpyrido[1,2-a] benzimidazoles by a copper-catalyzed inter-and intramolecular C-N coupling cascade process was designed and carried out, and the products were obtained in moderate to excellent yields (up to 93 %).
A direct intramolecular C-H amination reaction cocatalyzed by copper(II) and iron(III) as part of an efficient route for the synthesis of pyrido[1,2-a ]benzimidazoles from N-aryl-2-aminopyridines
Wang, Honggen,Wang, Yong,Peng, Changlan,Zhang, Jiancun,Zhu, Qiang
supporting information; experimental part, p. 13217 - 13219 (2010/11/04)
A novel and efficient synthesis of pyrido[1,2-a]benzimidazoles through direct intramolecular aromatic C-H amination of N-aryl-2-aminopyridines has been developed. The reaction, cocatalyzed by Cu(OAc)2 and Fe(NO 3)3?9H
New Method for the Synthesis of Pyridobenzimidazole
Prostakov, N. S.,Varlamov, A. V.,Shendrik, I. V.,Anisimov, B. N.,Krapivko, A. P.,et al.
, p. 1101 - 1103 (2007/10/02)
A catalytic method for the conversion of α-(phenylamino)pyridines to pyridobenzimidazoles was developed.
