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

Autor(es)

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]

Afiliação do(s) autor(es)

^[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

• Tipo de documento: Artigo Científico
• Fonte: RSC ADVANCES; v. 6, n. 10, p. 8021-8031, 2016.
• Citações Web of Science: 14

Resumo

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. (AU)

• Processo FAPESP: 15/17141-1 - Desenvolvimento e Estudos Mecanísticos de Novas Metodologias Sintéticas para Síntese de Compostos Bioativos
• Beneficiário: Ricardo Samuel Schwab
• Modalidade de apoio: Auxílio à Pesquisa - Regular
• Processo FAPESP: 14/50249-8 - Green chemistry: sustainable synthetic methods employing benign solvents, safer reagents, and bio-renewable feedstock
• Beneficiário: Arlene Gonçalves Corrêa
• Modalidade de apoio: Auxílio à Pesquisa - Programa Centros de Pesquisa em Engenharia