1092-65-5Relevant academic research and scientific papers
Regiodivergent synthesis of functionalized pyrimidines and imidazoles through phenacyl azides in deep eutectic solvents
Vitale, Paola,Cicco, Luciana,Cellamare, Ilaria,Perna, Filippo M.,Salomone, Antonio,Capriati, Vito
, p. 1915 - 1923 (2020/08/17)
We report that phenacyl azides are key compounds for a regiodivergent synthesis of valuable, functionalized imidazole (32–98% yield) and pyrimidine derivatives (45–88% yield), with a broad substrate scope, when using deep eutectic solvents [choline chloride (ChCl)/glycerol (1:2 mol/mol) and ChCl/urea (1:2 mol/mol)] as environmentally benign and non-innocent reaction media, by modulating the temperature (25 or 80 °C) in the presence or absence of bases (Et3N).
Synthesis of 2-aroyl-(4 or 5)-aryl-1H-imidazoles and 2-hydroxy-3,6-diaryl- pyrazines via a cascade process
Liu, Cong,Dai, Rong J.,Yao, Guo W.,Deng, Yu L.
, p. 146 - 163 (2014/04/17)
The synthesis of (4 or 5)-aryl-2-aroyl-1H-imidazoles and 2-hydroxy-3,6-diarylpyrazines from aryl methyl ketones via a cascade process of DMSO-HBr oxidation and Debus reaction was investigated. Owing to the simple starting materials, mild conditions, easy operation, high bioactivity of imidazole and pyrazine derivatives, this protocol has great potential in medicinal chemistry.
Discovery of 4-aryl-2-benzoyl-imidazoles as tubulin polymerization inhibitor with potent antiproliferative properties
Xiao, Min,Ahn, Sunjoo,Wang, Jin,Chen, Jianjun,Miller, Duane. D.,Dalton, James T,Li, Wei
, p. 3318 - 3329 (2013/06/26)
A series of 4-aryl-2-benzoyl-imidazoles were designed and synthesized based on our previously reported 2-aryl-4-benzoyl-imidazole (ABI) derivatives. The new structures reversed the aryl group and the benzoyl group of previous ABI structures and were named as reverse ABI (RABI) analogues. RABIs were evaluated for biological activity against eight cancer cell lines including multidrug-resistant cancer cell lines. In vitro assays indicated that several RABI compounds had excellent antiproliferative properties, with IC50 values in the low nanomolar range. The average IC50 of the most active compound 12a is 14 nM. In addition, the mechanism of action of these new analogues was investigated by cell cycle analysis, tubulin polymerization assay, competitive mass spectrometry binding assay, and molecular docking studies. These studies confirmed that these new RABI analogues maintain their mechanisms of action by disrupting tubulin polymerization, similar to their parental ABI analogues.
One-pot synthesis of disubstituted imidazole derivatives from α-azido ketones catalyzed by potassium ethylxanthate
Chen, Jun,Chen, Wenteng,Yu, Yongping,Zhang, Guolin
supporting information, p. 1572 - 1575 (2013/04/23)
An efficient, novel procedure for the synthesis of new imidazole derivatives from α-azido ketones is described. This reaction proceeds via dimerization of aryl glyoxal imino generated from α-azido ketones in the presence of potassium ethylxanthate as a catalyst. A possible mechanism for the entire sequence is proposed.
Microwave-assisted metal-free synthesis of 2,8-diaryl-6-aminoimidazo-[1,2- a]pyridine via amine-triggered benzannulation
Nagaraj, Muthupandi,Boominathan, Muthusamy,Muthusubramanian, Shanmugam,Bhuvanesh, Nattamai
supporting information; experimental part, p. 1353 - 1357 (2012/07/01)
An efficient microwave-assisted metal-free amino benzannulation of aryl(4-aryl-1-(prop-2-ynyl)-1H-imidazol-2-yl)methanone with dialkylamines afforded a variety of 2,8-diaryl-6-aminoimidazo[1,2-a]pyridine in moderate to excellent yield. Georg Thieme Verlag Stuttgart · New York.
