Effect of Dimethyl Sulfoxide and Dimethylformamide on the Stability of 4-Halo-8-quinolinols |
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Authors: | Herman Gershon Donald D. Clarke John J. McMahon |
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Affiliation: | (1) Department of Chemistry, Fordham University, Bronx, NY 10458-9993, USA, US;(2) New York Botanical Garden, Bronx, NY 10458-9993, USA, US |
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Abstract: | Summary. Polyhalo-8-quinolinols with chlorine or bromine in position 4 were not stable in DMSO or DMF. The degradation product from 4,5-dichloro-8-quinolinol was 5-chloro-4,8-quinolindiol and the major product from 4,5-dibromo-8-quinolinol was 3,5-dibromo-4,8-quinolindiol. 4,5,7-Trichloro- and 4,5,7-tribromo-8-quinolinols yielded similar hydrolytic products, and for the bromo compound, a rebrominated product in DMSO. In DMF rebromination did not occur. In pyridine-d5 these reactions did not take place, indicating a special ability of DMSO and DMF to cause such hydrolysis at position 4 of 4-halo-8-quinolinols.Received December 13, 2002; accepted January 7, 2003Published online June 23, 2003 |
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Keywords: | . Degradation of 4-halo-8-quinolinols in DMSO and DMF 4-Halo-8-quinolinols stable in pyridine-d5 5-Chloro-4,8-quinolindiol 5-Bromo-4,8-quinolindiol 3,5-Dibromo-4,8-quinolindiol. |
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