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Synthesis of Five-Membered Nitroazoles

  • L. Larina
  • V. Lopyrev
Chapter
Part of the Topics in Applied Chemistry book series (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.

Keywords

Nitro Group Imidazole Ring Pyrazole Ring Thiazole Ring Energetic Compound 
These keywords were added by machine and not by the authors. This process is experimental and the keywords may be updated as the learning algorithm improves.

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Copyright information

© Springer Science+Business Media, LLC 2009

Authors and Affiliations

  1. 1.Favorsky Irkutsk Institute of ChemistryIrkutskRussian

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