Synthesis of 2, 1-benzisoxazoles by nucleophilic substitution of hydrogen in nitroarenes activated by the azole ring

NT Pokhodylo, YO Teslenko, VS Matiychuk…

Index: Pokhodylo, Nazariy T.; Teslenko, Yuriy O.; Matiychuk, Vasyl S.; Obushak, Mykola D. Synthesis, 2009 , # 16 p. 2741 - 2748

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Citation Number: 7

Abstract

Abstract 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- ...