Jump to main content
Jump to site search


N-(2-Fluoro-2,2-dinitroethyl)azoles: Novel assembly of diverse explosophoric building blocks for energetic compounds design

Abstract

Although desirable from an energetic materials chemistry perspective, nitroazoles bearing oxygen-rich explosophoric units at a nitrogen atom of the ring are highly challenging target using current literature approaches. In this paper, we report the first simple two-step protocol to efficiently make unprecedented N-(2-fluoro-2,2,-dinitroethyl) derivatives of imidazole, pyrazole, triazole, and tetrazole. 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, nitro group, and can be extended to other structurally attractive electron-deficient NH-heterocycles.

Back to tab navigation

Supplementary files

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., 2018, Accepted Manuscript
  •   Request permissions

    N-(2-Fluoro-2,2-dinitroethyl)azoles: Novel assembly of diverse explosophoric building blocks for energetic compounds design

    N. V. Palysaeva, A. G. Gladyshkin, I. A. Vatsadze, K. Suponitsky, D. E. Dmitriev and A. B. Sheremetev, Org. Chem. Front., 2018, Accepted Manuscript , DOI: 10.1039/C8QO01173G

Search articles by author

Spotlight

Advertisements