3663-19-2Relevant academic research and scientific papers
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.
