36386-83-1

Upstream product

• 6206-85-5 (E)-2-phenyl-2H-1,2,3-triazole-4-carbaldehyde oxime 
• 41886-30-0 phenylhydrazono-malonaldehyde-dioxime 
• 108-24-7 acetic anhydride 
• 151-50-8 potassium cyanide 
• 51337-55-4 KP-23194 
• 3213-80-7 2-phenyl-1,2,3-triazole-4-carboxaldehyde 
• 77896-39-0 2-phenyl-2H-1,2,3-triazole 1-oxide 
• 77896-38-9 2-phenylhydrazonoglyoxal 1-oxime 
• 100-63-0 phenylhydrazine 
• 20672-18-8 2-(phenylhydrazono)ethanal 

Downstream Products

• 212329-22-1 5-(2-phenyl-1,2,3-triazol-4-yl)tetrazole 
• 26825-69-4 2-(2,4-dinitro-phenyl)-2H-[1,2,3]triazole-4-carboxylic acid 
• 212329-22-1 5-(2-phenyl-1,2,3-triazol-4-yl)tetrazole 
• 57352-20-2 4-amino-4-(2-phenyl-2H-[1,2,3]triazol-4-yl)-but-3-en-2-one 

Relevant academic research and scientific papers

Nitration of 4-Substituted 2-Phenyl-1,2,3-triazoles

Substituent in position 4 of the heteroring influences the nitration of 2-phenyl-1,2,3-triazoles. Electron-donor substituents favor nitration at the heteroring.

Oxidative Transformation of Pyrazole into Triazole. Novel Synthesis of 4-Cyano-2H-1,2,3-triazole Derivatives

Oxidation of 3,5-diamino-4-arylhydrazonopyrazoles with lead(IV) tetra-acetate provided 2-aryl-4-cyano-2H-1,2,3-triazoles in moderate yield.Tentative mechanisms via pyrazolotriazole and/or nitrene intermediates are proposed for this novel ring transformati

1,2,3-Triazoles produced from 5-Substituted N-Methoxytriazolium Salts

Five reactions, two of which are new, have been observed when 5-substituted 1-methoxy-2-phenyltriazolium salts react with nucleophiles: (i) addition to C-4 with elimination of methanol to give unsymmetrically 4,5-disubstituted triazoles; (ii) displacement of the 5-substituent followed by secondary reactions to give a symmetrically 4,5-disubstituted triazole, a 5-substituted triazole N-oxide, a 4-substituted triazole, or a disubstituted benzeneazoacetonitrile; (iii) deprotonation of the N-methoxy-group with elimination of formaldehyde; (iv) demethylation; (v) abstraction of an α-proton from a 5-alkyl group followed by nucleophilic addition and elimination of methanol to give an α-substituted 5-alkyltriazole.The reactions are of synthetic potential as a means of introducing one or two substituents in the 1,2,3-triazole system.

Electrophilic and Nucleophilic Substitution in the Triazole N-Oxides and N-Methoxytriazolium Salts: Preparation of Substituted 1,2,3-Triazoles

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.