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Issue 2, 2019
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N-(2-Fluoro-2,2-dinitroethyl)azoles: a novel assembly of diverse explosophoric building blocks for energetic compound design

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Abstract

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.

Graphical abstract: N-(2-Fluoro-2,2-dinitroethyl)azoles: a novel assembly of diverse explosophoric building blocks for energetic compound design

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Publication details

The article was received on 30 Oct 2018, accepted on 30 Nov 2018 and first published on 05 Dec 2018


Article type: Research Article
DOI: 10.1039/C8QO01173G
Citation: Org. Chem. Front., 2019,6, 249-255

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    N-(2-Fluoro-2,2-dinitroethyl)azoles: a novel assembly of diverse explosophoric building blocks for energetic compound design

    N. V. Palysaeva, A. G. Gladyshkin, I. A. Vatsadze, K. Yu. Suponitsky, D. E. Dmitriev and A. B. Sheremetev, Org. Chem. Front., 2019, 6, 249
    DOI: 10.1039/C8QO01173G

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