Synthesis of arylselanyl-1H-1,2,3-triazole-4-carboxylates by organocatalytic cycloaddition of azidophenyl arylselenides with beta-keto-esters

Autor(es)

Seus, Natalia ^[1] ; Goncalves, Loren C. ^[1] ; Deobald, Anna M. ^[2] ; Savegnago, Lucielli ^[3] ; Alves, Diego ^[1] ; Paixao, Marcio W. ^[2]

Afiliação do(s) autor(es)

^[1] Univ Fed Pelotas, UFPel, Lab Sintese Organ Limpa, LASOL, CCQFA, Pelotas, RS - Brazil

^[2] Univ Fed Sao Carlos, Lab Sintese Prod Nat, BR-13565905 Sao Carlos, SP - Brazil

^[3] Univ Fed Pelotas, UFPel, GPN, CDTec, Pelotas, RS - Brazil

• Tipo de documento: Artigo Científico
• Fonte: Tetrahedron; v. 68, n. 51, p. 10456-10463, DEC 23 2012.
• Citações Web of Science: 54

Resumo

The beta-enaminone-azide cycloaddition has been used for the synthesis of arylselanyl-1H-1,2,3-triazole-4-carboxylates by reaction of azidophenyl arylselenides with beta-keto-esters. The cycloaddition reactions were performed under mild conditions, reacting various azidophenyl arylselenides and beta-keto-esters using catalytic amount of Et2NH (1 mol %) and the corresponding products were obtained in good to excellent yields. Reactions using focused microwave irradiation reduced considerably the reaction time of this organocatalytic protocol from hours to few minutes, which makes this protocol useful and an attractive approach for the synthesis of high-functionalized 1,2,3-triazoles. (C) 2012 Elsevier Ltd. All rights reserved. (AU)

• Processo FAPESP: 09/07281-0 - Organocatálise assimétrica: preparação de novos organocatalisadores e desenvolvimento de novas metodologias
• Beneficiário: Márcio Weber Paixão
• Modalidade de apoio: Auxílio à Pesquisa - Jovens Pesquisadores