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Copper (I)-mediated tandem A3 coupling/[3 + 2] cycloaddition chemoselective synthesis of 4H-[1,2,3]triazolo[1,5-a]indoles
Catalysis Communications ( IF 3.4 ) Pub Date : 2017-12-27 , DOI: 10.1016/j.catcom.2017.12.020
Ramalingam Boobalan , Chinpiao Chen , Gene-Hsian Lee

The copper (I) mediated tandem reaction of A3 coupling followed by a [3 + 2] cycloaddition methodology is developed for the first synthesis of structurally interesting 3-aryl/alkyl/silyl-4-amino-4H-[1,2,3]triazolo[1,5-a]indoles from various 2-azidobenzaldehydes, secondary amines, and terminal alkynes. The optimal reaction conditions of this one-pot tandem reaction are simple, performed at room temperature, and produce the corresponding products with high yields (up to 84%). The intermolecular [3 + 2] cycloaddition of 2-azidobenzaldehydes and terminal alkynes is found to be the competitive reaction for the presently developed tandem reaction with 2-triazole benzaldehydes as the minor products. The latter were also isolated and characterized.



中文翻译:

铜(I)介导的串联A 3偶联/ [3 + 2]环加成化学选择性合成4 H- [1,2,3]三唑[1,5- a ]吲哚

开发了铜(I)介导的A 3偶联串联反应,然后是[3 ​​+ 2]环加成方法,用于首次合成结构上令人感兴趣的3-芳基/烷基/甲硅烷基-4-氨基-4 H- [1,2 ,3-]三唑并[1,5- a ]吲哚,来自各种2-叠氮基苯甲醛,仲胺和末端炔烃。此一锅串联反应的最佳反应条件很简单,可在室温下进行,并能以高收率(最高84%)生产相应的产物。发现2-叠氮苯甲醛和末端炔的分子间[3 + 2]环加成反应是目前开发的以2-三唑苯甲醛为次要产物的串联反应的竞争反应。后者也被分离和表征。

更新日期:2017-12-27
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