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

来源：

RSC ADVANCES | 2016年 / 6卷 / 10期

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

页码：8021 / 8031

页数：11

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