Organocatalytic Synthesis of (Arylselanyl)phenyl-1H-1,2,3-triazole4-carboxamides by Cycloaddition between Azidophenyl Arylselenides and β-Oxo-amides

• Published in: European journal of organic chemistry Vol. 2014; no. 5; pp. 1059 - 1065
• Main Authors: Seus, Natalia, Goldani, Bruna, Lenardao, Eder J., Savegnago, Lucielli, Paixao, Marcio W., Alves, Diego
• Format: Journal Article
• Language: English
• Published: WEINHEIM Wiley 01.02.2014
• Subjects: Chemistry; Chemistry, Organic; Physical Sciences; Science & Technology; beta-Oxoamides; DOMINO REACTION; AZIDE-ALKYNE CYCLOADDITION; ONE-POT SYNTHESIS; Organoselenium compounds; CLICK CHEMISTRY; CATALYZED INTRAMOLECULAR CYCLIZATION; 1,2,3-TRIAZOLE; EFFICIENT SYNTHESIS; Organocatalysis; 1,2,3-Triazoles; Cycloaddition; ORGANOSELENIUM; BIOLOGICAL EVALUATION; Selenium; DERIVATIVES
• ISSN: 1434-193X; 1099-0690
• DOI: 10.1002/ejoc.201301547

We describe the use of -oxo-amides in organocatalytic cycloaddition with aryl azidophenyl selenides. The cycloaddition reactions were performed under mild conditions, with -oxo-amides and aryl azidophenyl selenides in the presence of a catalytic amount of Et2NH (5 mol-%), and the corresponding products were obtained in good to excellent yields. This organocatalytic methodology tolerated a range of substituents either in the -oxo-amides or in the aryl azidophenyl selenides and proved to be an efficient methodology for the combinatorial synthesis of new selenium-containing triazole compounds.