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Dinitrofuroxan cycloreversion as a novel general approach for the synthesis of nitroazoles

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Abstract

A novel general approach towards various nitroazoles via tandem process involving dinitrofuroxan cycloreversion followed by [3+2] cycloaddition of generated in situ nitroformonitrile oxide is developed. The reaction is promoted by addition of catalytic amounts of ionic liquids. Plausible mechanisms of the described processes based on quantum chemical calculations are proposed.

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Authors and Affiliations

  1. N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky prosp., 119991, Moscow, Russian Federation

    L. L. Fershtat, D. V. Khakimov & N. N. Makhova

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  1. L. L. Fershtat
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  2. D. V. Khakimov
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  3. N. N. Makhova
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Correspondence to N. N. Makhova.

Additional information

For short communication see Ref. 1.

Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 2, pp. 0415—0422, February, 2015.

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Fershtat, L.L., Khakimov, D.V. & Makhova, N.N. Dinitrofuroxan cycloreversion as a novel general approach for the synthesis of nitroazoles. Russ Chem Bull 64, 415–422 (2015). https://doi.org/10.1007/s11172-015-0878-6

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  • DOI: https://doi.org/10.1007/s11172-015-0878-6

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