34658-68-9Relevant academic research and scientific papers
Metal-free synthesis of aminomethylated imidazoheterocycles: dual role of tert-butyl hydroperoxide as both an oxidant and a methylene source
Patel, Om P. S.,Nandwana, Nitesh Kumar,Sah, Ajay Kumar,Kumar, Anil
, p. 8620 - 8628 (2018)
A novel and efficient aminomethylation approach has been developed for the regioselective functionalization of imidazoheterocycles under metal-free conditions. A wide range of imidazoheterocycles and 2/4-aminoazaheterocycles successfully provided corresponding aminomethylated imidazoheterocycles in moderate to excellent (33-80%) yields. The isotopic labelling study suggested that TBHP played a dual role as both an oxidant and a methylene source in this transformation. The developed protocol follows a radical pathway which is supported by radical trapping experiments.
One-Pot Synthesis of 3-Methyl-2-arylimidazo[1,2-a]pyridines Using Calcium Carbide as an Alkyne Source
Chen, Wei,Li, Zheng
, p. 76 - 84 (2022/01/03)
An efficient method for the construction of 3-methyl-2-arylimidazo[1,2-a]pyridines from the reactions of calcium carbide, 2-aminopyridines, and aromatic aldehydes is described. The notable advantages for this strategy include the use of an inexpensive and
CuCl2-catalyzed N[sbnd]O bond cleavage of oxime esters: Approach to imidazoheterocycles and furo[3,2-c]chromenyl fused imidazoles
Gudimella, Santosh K.,Kaur, Amanpreet,Kumar, Ram,Samanta, Sampak
supporting information, (2020/07/08)
An articulate approach to a diverse set of imidazoheterocycles in good to high yields via a copper-catalyzed aza-annulation of several oxime esters with a group of 2-amino-azaarenes was developed. The above cyclization reaction probably proceeds via a single electron transfer process which embodies a new technique for creating two new C[sbnd]N bonds for imidazole ring synthesis. Gratifyingly, the implementation of this chemistry could be further stretched to the synthesis of a novel class of fused imidazoles bearing a furo[3,2-c]chromene moiety via a sequential C[sbnd]N bond formation, followed by C(sp2)-H functionalization/5-endo-dig-oxacyclization (C[sbnd]C and C[sbnd]O bonds) of in situ produced fused imidazoles with cyclic enynones in the presence of copper(II) as a π-electrophilic Lewis acid catalyst.
Visible-light-promoted sulfonylmethylation of imidazopyridines
Mi, Xia,Kong, Yuanfang,Zhang, Jingyu,Pi, Chao,Cui, Xiuling
, p. 2295 - 2298 (2019/10/28)
The visible light promoted C–H sulfonylmethylation of imidazopyridines with easily accessible bromomethyl sulfones under mild reaction conditions was described. This protocol provides an effective and practical access to sulfonylmethylated imidazopyridines with good functional group tolerance. The desired products were provided in moderate to excellent yields for 50 examples at room temperature. The method could also be an attractive strategy to install a methyl group on imidazopyridines.
Metal-free, base catalyzed oxidative amination and denitration reaction: Regioselective synthesis of 3-arylimidazo[1,2-a]pyridines
Devi, Elango Sankari,Alanthadka, Anitha,Nagarajan, Subbiah,Sridharan, Vellaisamy,Maheswari, Chockalingam Uma
supporting information, p. 3485 - 3489 (2018/08/22)
A metal-free, regioselective strategy for the synthesis of 3-arylimidazo[1,2-a]pyridines from β-nitrostyrenes and 2-aminopyridines using triethylamine as the catalyst and H2O2 (30% aq.) as the oxidant is reported. The use of an inexp
Au-catalyzed domino process synthesis of imidazo[1,2-a]pyridines from 2-aminopyridine and N-tosylhydrazones: An efficient C[sbnd]N bond formation reaction
Guo, Pengfeng,Huang, Shuyu,Mo, Jiaxian,Chen, Xiaoyan,Jiang, Hangqi,Chen, Weifeng,Cai, Hehuan,Zhan, Haiying
, p. 43 - 46 (2016/11/25)
A novel Au-catalyzed domino reaction for the synthesis of imidazo[1,2-a]pyridines from 2-aminopyridine and N-tosylhydrazones has been developed using molecular oxygen. It represents a new strategy for the formation of C[sbnd]N bonds. This transformation demonstrated a broad tolerance toward the substrates and allowed the generation of a diverse imidazo[1,2-a]pyridine derivatives with good yields.
Regiocontrolled functionalization of 2,3-dihalogenoimidazo[1,2-a]pyridines by Suzuki-Miyaura and Sonogashira cross-coupling reactions
Delaye,Pénichon,Allouchi,Enguehard-Gueiffier,Gueiffier
, p. 4199 - 4203 (2017/07/10)
An efficient method for regiocontrolled functionalization of 2,3-dihalogenoimidazo[1,2-a]pyridine was developed. This sequence allowed the selective introduction of aryl, heteroaryl, alkyl and alkynyl substituents at both 2- and 3-positions, by using Suzu
Copper-Catalyzed Aerobic Oxidative Cyclization of Ketoxime Acetates with Pyridines for the Synthesis of Imidazo[1,2-a]pyridines
Ren, Zhi-Hui,Zhao, Mi-Na,Yi, Yukun,Wang, Yao-Yu,Guan, Zheng-Hui
, p. 1920 - 1926 (2016/06/15)
A copper(I)-catalyzed aerobic oxidative coupling of ketoxime acetates with simple pyridines for the synthesis of imidazo[1,2-a]pyridines has been developed. This reaction tolerates a wide range of functional groups and it affords a series of valuable imidazo[1,2-a]pyridines in high yields under mild conditions.
Transition-Metal-Free Tandem Chlorocyclization of Amines with Carboxylic Acids: Access to Chloroimidazo[1,2-α]pyridines
Xiao, Xinsheng,Xie, Ying,Bai, Siyi,Deng, Yuanfu,Jiang, Huanfeng,Zeng, Wei
supporting information, p. 3998 - 4001 (2015/09/01)
An efficient one-pot and transition-metal-free chlorocyclization cascade of 2-aminopyridines with aliphatic carboxylic acids is reported. This transformation provides a novel approach to 2-chloro- or 3-chloro-substituted imidazo[1, 2-α]pyridines with a br
Highly efficient and eco-friendly protocol to functionalized imidazoles via ring-opening of α-nitro epoxides
Guo, Xiao,Shao, Jiaan,Liu, Huan,Chen, Binhui,Chen, Wenteng,Yu, Yongping
, p. 51559 - 51562 (2015/06/25)
A simple and direct synthesis of functionalized imidazoles from α-nitro-epoxides and amidines was developed. This reaction could proceed smoothly in a highly efficient and eco-friendly manner in moderate to excellent yields. A plausible mechanism has also
