77896-41-4Relevant articles and documents
1,2,3-Triazole N-Oxides. II. Synthesis of Substituted 4(5)-Ethoxycarbonyl-1,2,3-triazole N-Oxides
Kirillova,Shul'gina,Shafeev,Al'mukhamedov,Vereshchagin
, p. 1051 - 1054 (2007/10/03)
Oxidative cyclization of ethyl 2-hydrazono-3-hydroxyimino- and 3-hydrazono-2-hydroxyiminobutanoates in the presence of γ-MnO2 yields isomeric 4(5)-methyl-2-phenyl-5(4)-ethoxycarbonyl-1,2,3-triazole 1-oxides. Alkaline hydrolysis and ammonolysis
Electrophilic and Nucleophilic Substitution in the Triazole N-Oxides and N-Methoxytriazolium Salts: Preparation of Substituted 1,2,3-Triazoles
Begtrup, Mikael,Holm, John
, p. 503 - 513 (2007/10/02)
2-Phenyltriazole 1-oxides are activated at C-5 towards both electrophilic and nucleophilic attack.The N-oxides can be selectively halogenated and, in turn, the halogen replaced by strong nucleophiles.On subsequent deoxygenation, the N-oxides yield halogeno-, methylthio-, and methoxy-triazoles.Methylation produces N-methoxytriazolium salts in which H-5 can be replaced by weak nucleophiles, e.g. fluoride ions.Thus fluoro-, chloro-, hydroxy-, alkoxy-, acyloxy-, amino-, substituted amino-, azido-, nitro-, mercapto-, alkylthio-, acylthio-, and cyano-substituents can be introduced in the triazole nucleus.Alternatively deprotonated N-methoxytriazolium salts react with electrophiles producing substituted triazole N-oxides.The reactions of triazole N-oxides with hydrogen chloride to give chlorotriazoles, and with acetyl chloride to give acetoxytriazoles, are explained.