Heterocyclization of amino alcohols into saturated cyclic quaternary ammonium salts

Vinogradov, D. B.; Bulatov, P. V.; Petrov, E. Yu.; Tartakovsky, Vladimir A.

doi:10.1016/j.mencom.2020.11.031

Cited by 4 publications

(1 citation statement)

References 17 publications

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“…In particular, ionic compounds frequently have a higher density than atomically similar, non-ionogenic molecules because of the Coulomb forces influencing the formation of ordered and dense lattice structures in molecular assemblies [2][3][4][5][6]. Therefore, the combination of a heterocycle with an explosophoric group holds much promise for creating high-performance energy-rich structures [7,8].…”

Section: Introductionmentioning

confidence: 99%

A New Approach for the Synthesis of 2,3,4а,6,7,8а,9,10-Octaaza-4,8-dioxo-3,4,4a,7,8,8а,9,9a,10,10а-decahydroanthracene and High-Energy Performance Characterization of Its Dinitramide Salt

Glukhacheva,

Il’yasov,

Il’yasov

et al. 2023

Materials

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A simple, one-pot regioselective method for the synthesis of a high-nitrogen tricycle, 2,3,4а,6,7,8а,9,10-octaaza-4,8-dioxo-3,4,4a,7,8,8а,9,9a,10,10а-decahydroanthracene, with a yield of 27% was developed on a starting urea basis as a result of studies focused on finding new, more efficient approaches to the synthesis of high-energy derivatives of dinitramic acid (DNA). This tricycle was further treated to furnish 2,3,4а,6,7,8а,9,10-octaaza-4,8-dioxo-3,4,4a,7,8,8а,9a,10а-octohydroanthracene-9,10-ion-bis(dinitramide). The resultant salt of dinitramic acid exhibited inhibitory properties towards the burning rate of pyrotechnic compositions, reducing it by 30%, and possessed good thermal stability due to a high decomposition temperature above 260 °C and a low sensitivity to mechanical stimuli. The structural features of the new tricycle-based dinitramide salt were characterized via 2D NMR spectroscopy and double-focusing sector mass spectrometry (DFS).

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