Journal
SYNTHESIS-STUTTGART
Volume -, Issue 16, Pages 2741-2748Publisher
GEORG THIEME VERLAG KG
DOI: 10.1055/s-0029-1216875
Keywords
1H-1,2,3-triazole; tetrazole; nucleophilic substitution; 2,1-benzisoxazole; annulation
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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 sigma(H)-adduct was formed.
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