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

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

Journal

Organic Chemistry Frontiers
ISSN: 2052-4110 , E-ISSN: 2052-4129

Output data

Year: 2019, Volume: 6, Number: 2, Pages: 249-255 Pages count : 7 DOI: 10.1039/c8qo01173g

Authors

Palysaeva Nadezhda V. ¹ , Gladyshkin Aleksei G. ^1,2 , Vatsadze Irina A. ¹ , Suponitsky Kyrill Yu. ³ , Dmitriev Dmitry E. ⁴ , Sheremetev Aleksei B. ¹

Affiliations

1	N.D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Moscow 119991, Russian Federation
2	Mendeleev University of Chemical Technology, Moscow 125047, Russian Federation
3	A. N. Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences, Moscow 119991, Russian Federation
4	ChemRar Ltd, Khimki, Moscow region, Russian Federation

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.

Palysaeva N.V. , Gladyshkin A.G. , Vatsadze I.A. , Suponitsky K.Y. , Dmitriev D.E. , Sheremetev A.B.
N-(2-Fluoro-2,2-dinitroethyl)azoles: a novel assembly of diverse explosophoric building blocks for energetic compound design
Organic Chemistry Frontiers. 2019. V.6. N2. P.249-255. DOI: 10.1039/c8qo01173g WOS Scopus OpenAlex

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