Abstract
Cyclization with the formation of an N-N bond and simultaneous bromination, which lead to 3-bromo-1-pyrazoline 1,2-dioxides, apparently through a step involving the dinitroso derivative, occur in the reaction of sodium hypobromite with 1,3-hydroxylamino oximes. Dehydrobromination of the bromopyrazoline leads to the corresponding 3H-pyrazole. The same treatment of acetylacetone dioxime gives 4H-dibromo-3,5-dimethyl-4H-pyrazole 1,2-dioxide. which is readily hydrolyzed to the corresponding 4-oxo derivative. Data from the IR, UV, and PMR spectra are presented.
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Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. ?, pp. 248–251, February, 1944.
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Volodarskii, L.B., Tikhonova, L.A. Formation of 1-pyrazoline 1,2-dioxides by oxidation of 1,3-hydroxylamino oximes. Chem Heterocycl Compd 13, 198–201 (1977). https://doi.org/10.1007/BF00497877
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DOI: https://doi.org/10.1007/BF00497877