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

• Published in: Tetrahedron Vol. 68; no. 51; pp. 10456 - 10463
• Main Authors: Seus, Natália, Gonçalves, Loren C., Deobald, Anna M., Savegnago, Lucielli, Alves, Diego, Paixão, Márcio W.
• Format: Journal Article
• Language: English
• Published: OXFORD Elsevier Ltd 23.12.2012; Elsevier
• Subjects: 1,2,3-Triazoles; Azides; Chemistry; Chemistry, Organic; Cycloaddition; Organocatalysis; Organoselenium compounds; Physical Sciences; Science & Technology; 1,2,3-Triazoles; Azides; Cycloaddition; Organocatalysis; Organoselenium compounds; AZIDE-ALKYNE CYCLOADDITION; CHIRAL LIGANDS; CLICK CHEMISTRY; EFFICIENT SYNTHESIS; ENANTIOSELECTIVE ADDITION; CATALYZED 1,3-DIPOLAR CYCLOADDITION; SELENIUM; ORGANOSELENIUM; OPTIMIZATION; DERIVATIVES
• ISSN: 0040-4020; 1464-5416
• DOI: 10.1016/j.tet.2012.10.007

The β-enaminone–azide cycloaddition has been used for the synthesis of arylselanyl-1H-1,2,3-triazole-4-carboxylates by reaction of azidophenyl arylselenides with β-keto-esters. The cycloaddition reactions were performed under mild conditions, reacting various azidophenyl arylselenides and β-keto-esters using catalytic amount of Et2NH (1mol%) 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. [Display omitted]