Synthesis of 5-substituted tetrazoles via DNA-conjugated nitrile

被引：13
|
作者：
Du, Huang-Chi [1 ]
Matzuk, Martin M. [1 ]
Chen, Ying-Chu [1 ]
机构：
[1] Baylor Coll Med, Ctr Drug Discovery, Dept Pathol & Immunol, Houston, TX 77030 USA
来源：
ORGANIC & BIOMOLECULAR CHEMISTRY | 2020年 / 18卷 / 45期
关键词：
3+2 CYCLOADDITION; 1H-TETRAZOLES; DISCOVERY; AZIDE; CHEMISTRY; LIBRARIES; DESIGN;
D O I：
10.1039/d0ob02021d
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A zinc bromide-catalyzed synthesis of 5-substituted tetrazoles via DNA-conjugated nitriles using sodium azide has been developed. The protocol offered moderate to excellent yields of tetrazoles with a broad range of substrates, including a variety of functionalized aromatic, heterocyclic, and aliphatic nitriles. In addition, the electronic effect within the substrate scope was evaluated. DNA fidelity was assessed by ligation efficiency and amplifiability analysis. The ability to generate tetrazoles expands the diversity of heterocycles in the preparation of DNA-encoded chemical libraries.
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页码：9221 / 9226
页数：6
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