Phenylselanyl-1H-1,2,3-triazole-4-carbonitriles: synthesis, antioxidant properties and use as precursors to highly functionalized tetrazoles

被引:29
作者
Savegnago, Lucielli [1 ]
do Sacramento, Manoela [2 ]
Brod, Lucimar M. P. [1 ]
Fronza, Mariana G. [1 ]
Seus, Natalia [2 ]
Lenardao, Eder J. [2 ]
Paixao, Marcio W. [3 ]
Alves, Diego [1 ]
机构
[1] Univ Fed Pelotas, UFPel, CDTec, GPN, Pelotas, RS, Brazil
[2] Univ Fed Pelotas UFPel, CCQFA, LASOL, Lab Sintese Organ Limpa, BR-96010900 Pelotas, RS, Brazil
[3] Univ Fed Sao Carlos, Lab Sintese Prod Nat, BR-13565905 Sao Carlos, SP, Brazil
基金
巴西圣保罗研究基金会;
关键词
CATALYZED 1,3-DIPOLAR CYCLOADDITION; NITROGEN-RICH SALTS; CLICK CHEMISTRY; AZIDOPHENYL ARYLSELENIDES; OXIDATIVE STRESS; ENERGETIC MONO; COPPER; AZIDE; ORGANOSELENIUM; HETEROCYCLES;
D O I
10.1039/c5ra22445d
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
We describe herein our results on the synthesis, antioxidant properties and chemical diversification of phenylselanyl-1H-1,2,3-triazole-4-carbonitriles. These compounds were synthesized in high yields by the reaction of azidophenyl phenylselenides with a range of alpha-keto nitriles, using DMSO as the solvent in the presence of a catalytic amount of Et2NH (1 mol%). The synthesized compounds were screened for their in vitro antioxidant activity and 5-phenyl-1-(2-(phenylselanyl) phenyl)-1H-1,2,3-triazole-4-carbonitrile (3a) exhibited the highest antioxidant effect. In addition, the obtained triazoyl carbonitriles were readily transformed into more complex products via a cycloaddition protocol with NaN3, affording bifunctional hybrids containing triazole and tetrazole systems in good to excellent yields.
引用
收藏
页码:8021 / 8031
页数:11
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