Synthesis of 1,5-disubstituted tetrazole-1,2,3 triazoles hybrids via Ugi-azide/CuAAC

被引：15
|
作者：
Aguilar-Morales, Cesia M. [1 ]
de Loera, Denisse [2 ]
Contreras-Celedon, Claudia [1 ]
Cortes-Garcia, Carlos J. [1 ]
Chacon-Garcia, Luis [1 ]
机构：
[1] Univ Michoacana, Inst Invest Quim Biol, Lab Diseno Mol, Ciudad Univ, Morelia 58033, Michoacan, Mexico
[2] Univ Autonoma San Luis Potosi, Fac Ciencias Quim, San Luis Potosi, Mexico
来源：
SYNTHETIC COMMUNICATIONS | 2019年 / 49卷 / 16期
关键词：
1,5-Disubstituted tetrazole; 1,4-disubstituted-1,2,3-triazoles; hybrids compounds; multicomponent reaction; Ugi-azide; CARBOXYLIC-ACID ISOSTERES; CLICK CHEMISTRY; MULTICOMPONENT REACTIONS; MEDICINAL CHEMISTRY; AZIDE; CYCLOADDITION; 1,2,3-TRIAZOLES; HYBRIDIZATION; DERIVATIVES; INHIBITORS;
D O I：
10.1080/00397911.2019.1616301
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A new synthetic strategy to obtain new linked 1,5-disubstituted tetrazole-1,2,3-triazoles via the Ugi-azide reaction followed by a copper-catalyzed alkyne-azide reaction (CuAAC) was developed. This strategy used solvent-free conditions for the Ugi-azide reaction. This two-step strategy affords the products in moderate to good yields. To the best of our knowledge, this is the first report using the CuAAC reaction as a post-condensation process in an Ugi-azide reaction and therefore, the first describing the synthesis of 1,5-disubstituted tetrazole (1,5-DS-T) linked to the 1,2,3-triazole moiety, which are molecules that may have potential applications in medicinal chemistry. [GRAPHICS]
引用
收藏
页码：2086 / 2095
页数：10
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