1132769-65-3Relevant academic research and scientific papers
Carbene-Catalyzed α-Carbon Amination of Chloroaldehydes for Enantioselective Access to Dihydroquinoxaline Derivatives
Huang, Ruoyan,Chen, Xingkuan,Mou, Chengli,Luo, Guoyong,Li, Yongjia,Li, Xiangyang,Xue, Wei,Jin, Zhichao,Chi, Yonggui Robin
, p. 4340 - 4344 (2019/06/14)
An NHC-catalyzed α-carbon amination of chloroaldehydes was developed. Cyclohexadiene-1,2-diimines are used as amination reagents and four-atom synthons. Our reaction affords optically enriched dihydroquinoxalines that are core structures in natural products and synthetic bioactive molecules.
Metal-free tandem cyclization/hydrosilylation to construct tetrahydroquinoxalines
Pan, Yixiao,Chen, Changjun,Xu, Xin,Zhao, Haoqiang,Han, Jiahong,Li, Huanrong,Xu, Lijin,Fan, Qinghua,Xiao, Jianliang
supporting information, p. 403 - 411 (2018/02/07)
A one-pot tandem procedure involving cyclization and sequential hydrosilylation of imines and amides under the catalysis of B(C6F5)3 has been developed for the step-economical construction of 1,2,3,4-tetrahydroquinoxalines directly from readily available 1,2-diaminobenzenes, α-ketoesters and low-cost, safe polymethylhydrosiloxane (PMHS). This metal-free approach provides various products in good to excellent yields, and displays a wide range of substrate scope and a high degree of functional group tolerance even to reduction-sensitive moieties. The choice of hydrosilanes is critical to the catalysis, and PMHS has proved to be optimal. Decreasing the amount of PMHS could enable the reaction to stop at the 3,4-dihydroquinoxalin-2(1H)-one stage. The procedure is convenient and scalable, and neither a dried solvent nor an inert atmosphere is required. Moreover, the enantioselective construction of these products was explored, and promising results were achieved.
Novel HDAC6 isoform selective chiral small molecule histone deacetylase inhibitors
Smil, David V.,Manku, Sukhdev,Chantigny, Yves A.,Leit, Silvana,Wahhab, Amal,Yan, Theresa P.,Fournel, Marielle,Maroun, Christiane,Li, Zuomei,Lemieux, Anne-Marie,Nicolescu, Alina,Rahil, Jubrail,Lefebvre, Sylvain,Panetta, Anthony,Besterman, Jeffrey M.,Déziel, Robert
scheme or table, p. 688 - 692 (2009/08/15)
In an effort to identify HDAC isoform selective inhibitors, we designed and synthesized novel, chiral 3,4-dihydroquinoxalin-2(1H)-one and piperazine-2,5-dione aryl hydroxamates showing selectivity (up to 40-fold) for human HDAC6 over other class I/IIa HDACs. The observed selectivity and potency (IC50 values 10-200 nM against HDAC6) is markedly dependent on the absolute configuration of the chiral moiety, and suggests new possibilities for use of chiral compounds in selective HDAC isoform inhibition.
