Combination of Aryl Diselenides/Hydrogen Peroxide and Carbon-Nanotube/Rhodium Nanohybrids for Naphthol Oxidation: An Efficient Route towards Trypanocidal Quinones

被引:25
作者
de Carvalho, Renato L. [1 ]
Jardim, Guilherme A. M. [1 ]
Santos, Augusto C. C. [1 ]
Araujo, Maria H. [1 ]
Oliveira, Willian X. C. [1 ]
Bombaca, Ana Cristina S. [2 ]
Menna-Barreto, Rubem F. S. [2 ]
Gopi, Elumalai [3 ]
Gravel, Edmond [3 ]
Doris, Eric [3 ]
da Silva Junior, Eufranio N. [1 ]
机构
[1] Univ Fed Minas Gerais, Dept Chem, Inst Exact Sci, BR-31270901 Belo Horizonte, MG, Brazil
[2] Fiocruz MS, Inst Oswaldo Cruz, BR-21045900 Rio De Janeiro, RJ, Brazil
[3] Univ Paris Saclay, CEA, SCBM, F-91191 Gif Sur Yvette, France
关键词
carbon nanotubes; Chagas disease; oxidation; quinones; rhodium nanohybrid; selenium; HYDROGEN-PEROXIDE; BENZENESELENINIC ACID; CATALYTIC-OXIDATION; BETA-LAPACHONE; CANCER-CELLS; PHENOLS; HYDROQUINONE; DERIVATIVES; CYCLOADDITION; ANHYDRIDE;
D O I
10.1002/chem.201802773
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
This work reports a combination of aryl diselenides/hydrogen peroxide and carbon-nanotube (CNT)/rhodium nanohybrids (RhCNT) for naphthol oxidation towards the synthesis of 1,4-naphthoquinones and evaluation of their relevant trypanocidal activity. Under a combination of (PhSe)(2)/H2O2 in the presence of O-2 in iPrOH/hexane, several benzenoid (A-ring)-substituted quinones were prepared in moderate to high yields. We also studied the contribution of RhCNT as co-catalyst in this process and, in some cases, yields were improved. This method provides an efficient and versatile alternative for preparing A-ring-modified naphthoquinonoid compounds with relevant biological profile.
引用
收藏
页码:15227 / 15235
页数:9
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