1124239-41-3Relevant academic research and scientific papers
Synthesis of imidazo[1,2-a]quinoxalines by double Groebke reactions and inhibitory effects on radicals and DNA oxidation
Chen, Jia-Feng,Liu, Zai-Qun
, p. 1850 - 1859 (2017/03/10)
The o-phenylenediamine, aldehyde, and 2,4,4-trimethylpentan-2-yl isocyanide performed a Groebke 3CR to afford 2-aminoquinoxaline, which can react with an aldehyde and t-butyl isocyanide via another Groebke 3CR to give imidazo[1,2-a]quinoxaline. Exchanging two aldehydes in the sequential Groebke 3CR led to a couple of imidazo[1,2-a]quinoxaline isomer, in which the aldehyde moiety located at 2- or 4-position. The ferrocenyl group at 4-position in imidazo[1,2-a]quinoxaline was found to be active in trapping galvinoxyl radical, while the phenolic hydroxyl group at 2-position played a synergistic role with 4-ferrocenyl or 4-flavonyl group in scavenging 2,2′-diphenyl-1-picrylhydrazyl radical (DPPH). In addition, 4-ferrocenyl with N,N-dimethylaminophenyl group at 2-position was able to quench 2,2′-azinobis(3-ethylbenzothiazoline-6-sulfonate) cationic radical (ABTS+[rad]). Moreover, the combination of 4-ferrocenyl with 2-phenyl group (bearing para-N,N-dimethylamino or hydroxyl group) exhibited high inhibitory effect on DNA oxidation induced by 2,2′-azobis(2-amidinopropane hydrochloride) (AAPH).
Imidazo[l,2-a]quinoxalines accessed via two sequential isocyanide-based multicomponent reactions
Krasavin, Mikhail,Shkavrov, Sergey,Parchinsky, Vladislav,Bukhryakov, Konstantin
experimental part, p. 2627 - 2629 (2009/07/25)
A novel synthetic protocol toward imidazo[l,2-a]quinoxa-lines has been developed. It includes two isocyanide-based multicomponent reactions sequentially introducing four diversity elements to the final products
