A niobium-catalyzed coupling reaction of α-keto acids with ortho-phenylenediamines: synthesis of 3-arylquinoxalin-2(1H)-ones

被引：25
作者：
Ebersol, Camila [1 ]
Rocha, Nicole [1 ]
Penteado, Filipe [1 ]
Silva, Mardi S. [1 ]
Hartwig, Daniela [1 ]
Lenardao, Eder J. [1 ]
Jacob, Raquel G. [1 ]
机构：
[1] Univ Fed Pelotas UFPel, LASOL CCQFA, POB 354, BR-96010900 Pelotas, RS, Brazil
来源：
GREEN CHEMISTRY | 2019年 / 21卷 / 22期
关键词：
QUINOXALINONE DERIVATIVES; QUINOXALIN-2(1H)-ONES; DRUG; INHIBITORS; ARYLATION; POTENT; QUINOXALIN-2(H)-ONES; DECARBOXYLATION; CYCLIZATION; ANTITUMOR;
D O I：
10.1039/c9gc02662b
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
A general methodology to access valuable 3-arylquinoxalin-2(1H)-ones was developed, by the reaction of alpha-keto acids with ortho-phenylenediamines in the presence of ammonium niobium oxalate (ANO) as a catalyst. The reactions were conducted in only 10 min under ultrasonic irradiation as an alternative energy source, affording water as the only co-product. A total of twenty-three different 3-arylquinoxalin-2(1H)-ones were selectively obtained in good to excellent yields by this atom-efficient protocol. Additionally, H-1-N-15 HMBC experiments were used to reveal the regioisomerism of the obtained products.
引用
收藏
页码：6154 / 6160
页数：7
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