Ultrasound-promoted organocatalytic enamine-azide [3 + 2] cycloaddition reactions for the synthesis of ((arylselanyl)phenyl-1 H -1,2,3-triazol-4-yl)ketones

• Published in: Beilstein journal of organic chemistry Vol. 13; pp. 694 - 702
• Main Authors: Costa, Gabriel P, Seus, Natália, Roehrs, Juliano A, Jacob, Raquel G, Schumacher, Ricardo F, Barcellos, Thiago, Luque, Rafael, Alves, Diego
• Format: Journal Article
• Language: English
• Published: Germany 11.04.2017
• Subjects: organocatalysis; organoselenium compounds; cycloadditions; sonochemistry; 1,2,3-triazoles
• ISSN: 1860-5397; 1860-5397
• DOI: 10.3762/bjoc.13.68

The use of sonochemistry is described in the organocatalytic enamine-azide [3 + 2] cycloaddition between 1,3-diketones and aryl azidophenyl selenides. These sonochemically promoted reactions were found to be amenable to a range of 1,3-diketones or aryl azidophenyl selenides, providing an efficient access to new ((arylselanyl)phenyl-1 -1,2,3-triazol-4-yl)ketones in good to excellent yields and short reaction times. In addition, this protocol was extended to β-keto esters, β-keto amides and α-cyano ketones. Selanyltriazoyl carboxylates, carboxamides and carbonitriles were synthesized in high yields at short times of reaction under very mild reaction conditions.