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

被引：18

作者：

Costa, Gabriel P. ^{[1
]}

Seus, Natalia ^{[1
]}

Roehrs, Juliano A. ^{[1
]}

Jacob, Raquel G. ^{[1
]}

Schumacher, Ricardo F. ^{[1
]}

Barcellos, Thiago ^{[2
]}

Luque, Rafael ^{[3
]}

Alves, Diego ^{[1
]}

机构：

[1] Univ Fed Pelotas UFPel, CCQFA, LASOL, Lab Sintese Organ Limpa, POB 354, BR-96010900 Pelotas, RS, Brazil

[2] Univ Caxias do Sul, Lab Biotechnol Nat & Synthet Prod, Caxias Do Sul, RS, Brazil

[3] Univ Cordoba, Dept Quim Organ, Campus Rabanales, Cordoba, Spain

来源：

BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY | 2017年 / 13卷

关键词：

cycloadditions; organocatalysis; organoselenium compounds; sonochemistry; 1,2,3-triazoles; CATALYZED 1,3-DIPOLAR CYCLOADDITION; CLICK CHEMISTRY; ALKYNE CYCLOADDITION; AZIDOPHENYL ARYLSELENIDES; ASSISTED SYNTHESIS; TERMINAL ALKYNES; EFFICIENT; 1,2,3-TRIAZOLES; ORGANOSELENIUM; SONOCHEMISTRY;

D O I：

10.3762/bjoc.13.68

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

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.

引用

页码：694 / 702

页数：9

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