401571-48-0Relevant 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
Synthesis of 2,1-benzisoxazoles by nucleophilic substitution of hydrogen in nitroarenes activated by the azole ring
Pokhodylo, Nazariy T.,Teslenko, Yuriy O.,Matiychuk, Vasyl S.,Obushak, Mykola D.
experimental part, p. 2741 - 2748 (2010/02/28)
Reaction of 1-nitro-4-(1,2,3-triazolyl/tetrazolyl)benzenes with arylacetonitriles in an alcoholic medium in the presence of excess alkali gives novel 2,1-benzisoxazoles. These findings indicate a high reactivity of nitroarenes activated by the azole ring due to their electron-deficient character. Moreover, it was found that annulation of the isoxazole ring occurred regioselectively in disubstituted nitroarenes. In the case of 1-(4-nitrophenyl)-1H-tetrazole, the tetrazole ring cleaved faster than the sH-adduct was formed. Georg Thieme Verlag Stuttgart.
