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Synthesis of Five-Membered Nitroazoles

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Nitroazoles: Synthesis, Structure and Applications

Part of the book series: Topics in Applied Chemistry ((TAPP))

Abstract

Synthesis methods of various C- and N-nitroderivatives of five-membered azoles – pyrazoles, imidazoles, 1,2,3-triazoles, 1,2,4-triazoles, oxazoles, oxadiazoles, isoxazoles, thiazoles, thiadiazoles, isothiazoles, selenazoles and tetrazoles – are summarized and critically discussed. The special attention focuses on the nitration reaction of azoles with nitric acid or sulfuric–nitric acid mixture, one of the main synthetic routes to nitroazoles. The nitration reactions with such nitrating agents as acetylnitrate, nitric acid/trifluoroacetic anhydride, nitrogen dioxide, nitrogen tetroxide, nitronium tetrafluoroborate, N-nitropicolinium tetrafluoroborate are reported. General information on the theory of electrophilic nitration of aromatic compounds is included in the chapter covering synthetic methods. The kinetics and mechanisms of nitration of five-membered azoles are considered. The nitroazole preparation from different cyclic systems or from aminoazoles or based on heterocyclization is the subject of wide speculation. The particular section is devoted to the chemistry of extraordinary class of nitroazoles – polynitroazoles. Vicarious nucleophilic substitution (VNS) reaction in nitroazoles is reviewed in detail.

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  1. Favorsky Irkutsk Institute of Chemistry, Irkutsk, Russian

    L. Larina & V. Lopyrev

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Larina, L., Lopyrev, V. (2009). Synthesis of Five-Membered Nitroazoles. In: Nitroazoles: Synthesis, Structure and Applications. Topics in Applied Chemistry. Springer, New York, NY. https://doi.org/10.1007/978-0-387-98070-6_1

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