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

Abstract

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-1H-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.

Beilstein J. Org. Chem. 2017, 13, 694–702. doi:10.3762/bjoc.13.68

Authors:   Gabriel P. Costa; Natália Seus; Juliano A. Roehrs; Raquel G. Jacob; Ricardo F. Schumacher; Thiago Barcellos; Rafael Luque; Diego Alves
Journal:   Beilstein Journal of Organic Chemistry
Volume:   13
edition:   1
Year:   2017
Pages:   694
DOI:   10.3762/bjoc.13.68
Publication date:   11-Apr-2017
Facts, background information, dossiers
  • Cycloaddition
  • carboxylates
  • amides
More about Beilstein-Institut
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