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

Beilstein Journal of Organic Chemistry
Gabriel P CostaDiego Alves

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.

References

Aug 9, 2003·Journal of the American Chemical Society·Lac V LeeChi-Huey Wong
Dec 9, 2004·Chemical Reviews·Cristina W NogueiraJoão B T Rocha
May 5, 2005·Journal of the American Chemical Society·Antoni KrasińskiHartmuth C Kolb
Nov 17, 2005·Journal of the American Chemical Society·Li ZhangGuochen Jia
Dec 22, 2007·Organic Letters·Daniel FontMiquel A Pericàs
Jun 24, 2008·Journal of the American Chemical Society·Brant C BorenValery V Fokin
Feb 19, 2009·Chemical Reviews·Gelson PerinRodrigo Barroso Panatieri
Sep 24, 2009·Angewandte Chemie·Jason E HeinValery V Fokin
Oct 6, 2009·Angewandte Chemie·Diana M FreudendahlThomas Wirth
Nov 13, 2009·Journal of Combinatorial Chemistry·Giancarlo CravottoAlessandro Barge
Feb 11, 2011·Organic Letters·Issa SambIsabelle Leray
Jun 13, 2015·Chemical Communications : Chem Comm·Carolina G S LimaMárcio W Paixão
Jun 13, 2015·Chemical Communications : Chem Comm·Jubi JohnWim Dehaen
Jun 25, 2016·European Journal of Medicinal Chemistry·Eduardo H G da CruzEufrânio N da Silva Júnior

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Citations

Mar 14, 2019·Frontiers in Chemistry·Katia MartinaGiancarlo Cravotto
Dec 14, 2017·Chemical Record : an Official Publication of the Chemical Society of Japan ... [et Al.]·Diego AlvesMárcio W Paixão
Jan 26, 2021·Chemical Communications : Chem Comm·Tomas Opsomer, Wim Dehaen
Mar 19, 2021·Chemical Record : an Official Publication of the Chemical Society of Japan ... [et Al.]·Manoela SacramentoDiego Alves

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Methods Mentioned

BETA
nuclear magnetic resonance
column chromatography

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