Journal
BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY
Volume 13, Issue -, Pages 694-702Publisher
BEILSTEIN-INSTITUT
DOI: 10.3762/bjoc.13.68
Keywords
cycloadditions; organocatalysis; organoselenium compounds; sonochemistry; 1,2,3-triazoles
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Funding
- CNPq [306430/2013-4, 400150/2014-0, 447595/2014-8]
- CAPES
- FAPERGS [PRONEM 6/2551-0000240-1]
- Ciencia sem Fronteiras Program [303415/2014-2]
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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 beta-keto esters, alpha-keto amides and a-cyano ketones. Selanyltriazoyl carboxylates, carboxamides and carbonitriles were synthesized in high yields at short times of reaction under very mild reaction conditions.
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