N-(2-Fluoro-2,2-dinitroethyl)azoles: a novel assembly of diverse explosophoric building blocks for energetic compound design
文献信息
发布日期
2018-12-05
DOI
10.1039/C8QO01173G
影响因子
5.281
作者
Nadezhda V. Palysaeva, Irina A. Vatsadze, Kyrill Yu. Suponitsky, Dmitry E. Dmitriev, Aleksei B. Sheremetev
查看原文
摘要
Although desirable from an energetic materials chemistry perspective, nitroazoles bearing oxygen-rich explosophoric units at a nitrogen atom of the ring are a highly challenging target using current literature approaches. In this paper, we report the first simple two-step protocol to efficiently prepare unprecedented N-(2-fluoro-2,2,-dinitroethyl) derivatives of imidazoles, pyrazoles, triazoles, and tetrazoles. Michael addition of NH-azoles to 1,1-dinitroethene, generated from 1,1,1-trinitroethane, followed by fluorination provides the N-dinitrofluoroethylated nitrogen heterocycles in moderate to good overall yields. The syntheses employ azoles with electron-withdrawing groups, predominantly, the nitro group, and can be extended to other structurally attractive electron-deficient NH-heterocycles.
期刊推荐
Science
Kinetics and Catalysis
Journal of Catalysis
Pure and Applied Chemistry
Proceedings of the National Academy of Sciences of the United States of America
Journal of Heterocyclic Chemistry
Fibre Chemistry
Organic Preparations and Procedures International
Pharmacological Reviews
European Journal of Wood and Wood Products
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来源期刊
Organic Chemistry Frontiers
CiteScore:
7.8
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8.7%
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724
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