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N-[2,2-Bis(methoxy-NNO-azoxy)ethyl]pyrazoles

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Chemistry of Heterocyclic Compounds Aims and scope

The reaction of 2,2-bis(methoxy-NNO-azoxy)ethanol nitrate with pyrazole, 3-nitropyrazole, 4-nitropyrazole, or 3,4-dinitropyrazole allowed to obtain the respective N-[2,2-bis(methoxy-NNO-azoxy)ethyl]pyrazoles. In the case of 3-nitropyrazole, only the 3-nitro isomer was formed, while alkylation of 3,4-dinitropyrazole led to a mixture of 3,4- and 4,5-dinitro isomers in 7:1 ratio, which was difficult to separate. The obtained pyrazoles were characterized by 1H, 13C, and 15N NMR spectroscopy. X-ray structural studies were performed for the synthesized 3-NO2, 4-NO2, and 3,4-(NO2)2 derivatives.

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Acknowledgements

The work was funded by the Institute for Problems of Chemical Physics, Russian Academy of Sciences (topic “Design of energetic materials”) with financial support from the program No. 31 of the Presidium of the Russian Academy of Sciences “Basic foundations for dual-use technologies" (topic “Study of new approaches to the design of energetic compounds of enhanced effectiveness”) and the Ministry of Education and Science of the Russian Federation (Federal Target Program according to the Contract No. 14.613.21.0043 of November 10, 2015).

K. Yu. Suponitsky acknowledges the Russian Science Foundation (project RNF 16-13-10404) for financial support of structural studies. The authors are grateful to A. V. Chernyak for the acquisition of NMR spectra.

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Authors and Affiliations

  1. Institute for Problems of Chemical Physics, Russian Academy of Sciences, 1 Akademika Semenova Ave., Chernogolovka, 142432, Russia

    Igor N. Zyuzin

  2. A. N. Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences, 28 Vavilova St., Moscow, 119991, Russia

    Kirill Yu. Suponitsky

  3. N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky Ave., Moscow, 119991, Russia

    Igor L. Dalinger

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  1. Igor N. Zyuzin
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  2. Kirill Yu. Suponitsky
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Correspondence to Igor N. Zyuzin.

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The Supplemetary information file containing crystallographic data for compounds 5–7 and calculation of the enthalpies of formation for compounds 5–7, 10, is available from the journal website at http://link.springer.com/journal/10593.

Translated from Khimiya Geterotsiklicheskikh Soedinenii, 2017, 53(6/7), 702–709

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Zyuzin, I.N., Suponitsky, K.Y. & Dalinger, I.L. N-[2,2-Bis(methoxy-NNO-azoxy)ethyl]pyrazoles. Chem Heterocycl Comp 53, 702–709 (2017). https://doi.org/10.1007/s10593-017-2112-y

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