499141-95-6Relevant academic research and scientific papers
Synthesis of 1-(R-Phenyl)-5-(R-Methyl)-1H-1,2,3-triazole-4-carboxylic acids by one-pot tandem reaction
Pokhodylo, Nazariy T.,Matiychuk, Vasyl S.,Obushak, Mykola D.
experimental part, p. 1932 - 1938 (2010/09/05)
Substituted 1H-1,2,3-triazole-4-carboxylic acids were synthesized by a three-component reaction of arylazides, ethyl 4-chloro-3-oxobutanoate, and either O-or S-nucleophiles in the presence of a base catalyst. The reaction most probably proceeded as a [3+2] cyclocondensation reaction between arylazide and ethyl 4-chloro-3-oxobutanoate with the further nucleophilic substitution of chlorine in the chloromethyl group. Reaction optimization was performed to carry out the reaction with an O-nucleophile. Conditions were found under which diethyl 2,5-dihydroxyterephthalate (the product of self-condensation of two molecules of ethyl 4-chloro-3-oxobutanoate with the further oxidation by azide) was obtained. Copyright
Molecular Rearrangements of 4-Iminomethyl-1,2,3-Triazoles. Replacement of 1-Aryl Substituents in 1H-1,2,3-Triazole-4-carbaldehydes
L'abbe, Gerrit,Bruynseels, Maria,Delbeke, Pieter,Toppet, Suzanne
, p. 2021 - 2027 (2007/10/02)
The two structural isomers, 4 and 5, of 1-substituted-4-iminomethyl-1,2,3-triazoles are interconvertible when heated in dimethyl sulfoxide at 80 deg C.The equilibrium position depends on the electronic properties of the R-substituent, favoring 5 for R = alkyl, benzyl and anisyl, and 4 for p-chlorophenyl and p-nitrophenyl.An interesting application is the synthesis of 1-alkyl-1,2,3-triazole-4-carbaldehydes from 1-phenyl-1,2,3-triazole-4-carbaldehyde by Scheme I.The hydrazones 4i, j and the oxime 4k do not rearrange due to an unfavorable Z-configuration around the C=N bond, whereas the acyloximino derivative 4m is converted into the nitrile 11.The structures of the products have been fully characterized by 13C nmr spectroscopy and the mechanistic details of the rearrangement are discussed.
