期刊
ORGANIC LETTERS
卷 24, 期 3, 页码 799-803出版社
AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.1c03201
关键词
-
Bifunctional azides are important intermediates in the preparation of medicines and biochemical tool compounds due to their participation in Click reactions. However, little is known about the synthesis and characterization of azidopyridines bearing a halogen substituent. This study demonstrated the safety and versatility of nine azidopyridines bearing a single fluorine, chlorine, or bromine atom through differential scanning calorimetry and mechanical stress testing, showcasing their utility in a variety of reactions.
Owing to their participation in Click reactions, bifunctional azides are valuable intermediates in the preparation of medicines and biochemical tool compounds. Despite the privileged nature of pyridines among pharmaceutical scaffolds, reports of the synthesis and characterization of azidopyridines bearing a halogen substituent for further elaboration are almost completely unknown in the literature. As azidopyridines carry nearly equal numbers of nitrogen and carbon atoms, we hypothesized that safety concerns limited the application of these useful bifunctional building blocks in medicinal and biological chemistry. To address this concern, we prepared and characterized nine azidopyridines bearing a single fluorine, chlorine, or bromine atom. All were examined by differential scanning calorimetry (DSC), in which they demonstrated exotherms of 228-326 kJ/mol and onset temperatures between 119 and 135 degrees C. Selected azidopyridines were advanced to mechanical stress testing, in which impact sensitivity was noted for one regioisomer of C5H3FN4. The utility of these versatile intermediates was demonstrated through their use in a variety of Click reactions and the diversification of the halogen handles.
作者
我是这篇论文的作者
点击您的名字以认领此论文并将其添加到您的个人资料中。
推荐
暂无数据