77896-74-3Relevant academic research and scientific papers
Addition of Nitrite Ions to 1-Methoxy-1,2,3-triazolium Salts. Formation of Nitro and Hydroxy Substituted Triazoles
Begtrup, Mikael,Knudsen, Niels Ole
, p. 97 - 100 (2007/10/02)
Potassium and silver nitrite add to 1-methoxy-2-phenyltriazolium salts as ambident nucleophiles to give 4-nitro- and 4-hydroxytriazoles.If unsubstituted, the latter, via nitrosation and oxidation, affords 4-hydroxy-5-nitro-2-phenyltriazole.The hydroxytriazoles add to unchanged starting material producing bistriazolyl ethers.A nitro-substituted derivative of the latter displays photochromic properties.
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.
