Ultrasound-promoted organocatalytic enamine–azide [3 + 2] cycloaddition reactions for the synthesis of ((arylselanyl)phenyl-1H-1,2,3-triazol-4-yl)ketones
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 a...
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Beilstein-Institut
2017-04-01
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| Series: | Beilstein Journal of Organic Chemistry |
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| Online Access: | https://doi.org/10.3762/bjoc.13.68 |
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doaj-253323e1eb344a18b44c18595b41ea792021-02-02T01:36:05ZengBeilstein-InstitutBeilstein Journal of Organic Chemistry1860-53972017-04-0113169470210.3762/bjoc.13.681860-5397-13-68Ultrasound-promoted organocatalytic enamine–azide [3 + 2] cycloaddition reactions for the synthesis of ((arylselanyl)phenyl-1H-1,2,3-triazol-4-yl)ketonesGabriel P. Costa0Natália Seus1Juliano A. Roehrs2Raquel G. Jacob3Ricardo F. Schumacher4Thiago Barcellos5Rafael Luque6Diego Alves7Laboratório de Síntese Orgânica Limpa - LASOL - CCQFA - Universidade Federal de Pelotas - UFPel - P.O. Box 354 - 96010-900, Pelotas, RS, BrazilLaboratório de Síntese Orgânica Limpa - LASOL - CCQFA - Universidade Federal de Pelotas - UFPel - P.O. Box 354 - 96010-900, Pelotas, RS, BrazilLaboratório de Síntese Orgânica Limpa - LASOL - CCQFA - Universidade Federal de Pelotas - UFPel - P.O. Box 354 - 96010-900, Pelotas, RS, BrazilLaboratório de Síntese Orgânica Limpa - LASOL - CCQFA - Universidade Federal de Pelotas - UFPel - P.O. Box 354 - 96010-900, Pelotas, RS, BrazilLaboratório de Síntese Orgânica Limpa - LASOL - CCQFA - Universidade Federal de Pelotas - UFPel - P.O. Box 354 - 96010-900, Pelotas, RS, BrazilLaboratory of Biotechnology of Natural and Synthetic Products, Universidade de Caxias do Sul, Caxias do Sul, RS, BrazilDepartamento de Quimica Organica, Universidad de Cordoba, Campus de Rabanales, Cordoba, SpainLaboratório de Síntese Orgânica Limpa - LASOL - CCQFA - Universidade Federal de Pelotas - UFPel - P.O. Box 354 - 96010-900, Pelotas, RS, BrazilThe 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.https://doi.org/10.3762/bjoc.13.68cycloadditionsorganocatalysisorganoselenium compoundssonochemistry1,2,3-triazoles |
| collection |
DOAJ |
| language |
English |
| format |
Article |
| sources |
DOAJ |
| author |
Gabriel P. Costa Natália Seus Juliano A. Roehrs Raquel G. Jacob Ricardo F. Schumacher Thiago Barcellos Rafael Luque Diego Alves |
| spellingShingle |
Gabriel P. Costa Natália Seus Juliano A. Roehrs Raquel G. Jacob Ricardo F. Schumacher Thiago Barcellos Rafael Luque Diego Alves 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 cycloadditions organocatalysis organoselenium compounds sonochemistry 1,2,3-triazoles |
| author_facet |
Gabriel P. Costa Natália Seus Juliano A. Roehrs Raquel G. Jacob Ricardo F. Schumacher Thiago Barcellos Rafael Luque Diego Alves |
| author_sort |
Gabriel P. Costa |
| title |
Ultrasound-promoted organocatalytic enamine–azide [3 + 2] cycloaddition reactions for the synthesis of ((arylselanyl)phenyl-1H-1,2,3-triazol-4-yl)ketones |
| title_short |
Ultrasound-promoted organocatalytic enamine–azide [3 + 2] cycloaddition reactions for the synthesis of ((arylselanyl)phenyl-1H-1,2,3-triazol-4-yl)ketones |
| title_full |
Ultrasound-promoted organocatalytic enamine–azide [3 + 2] cycloaddition reactions for the synthesis of ((arylselanyl)phenyl-1H-1,2,3-triazol-4-yl)ketones |
| title_fullStr |
Ultrasound-promoted organocatalytic enamine–azide [3 + 2] cycloaddition reactions for the synthesis of ((arylselanyl)phenyl-1H-1,2,3-triazol-4-yl)ketones |
| title_full_unstemmed |
Ultrasound-promoted organocatalytic enamine–azide [3 + 2] cycloaddition reactions for the synthesis of ((arylselanyl)phenyl-1H-1,2,3-triazol-4-yl)ketones |
| title_sort |
ultrasound-promoted organocatalytic enamine–azide [3 + 2] cycloaddition reactions for the synthesis of ((arylselanyl)phenyl-1h-1,2,3-triazol-4-yl)ketones |
| publisher |
Beilstein-Institut |
| series |
Beilstein Journal of Organic Chemistry |
| issn |
1860-5397 |
| publishDate |
2017-04-01 |
| description |
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. |
| topic |
cycloadditions organocatalysis organoselenium compounds sonochemistry 1,2,3-triazoles |
| url |
https://doi.org/10.3762/bjoc.13.68 |
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