Effect of Dimethyl Sulfoxide and Dimethylformamide on the Stability of 4-Halo-8-quinolinols

被引：0

作者：

Herman Gershon

Donald D. Clarke

John J. McMahon

机构：

[1] Department of Chemistry,

[2] Fordham University,undefined

[3] Bronx,undefined

[4] NY 10458-9993,undefined

[5] USA,undefined

[6] New York Botanical Garden,undefined

[7] Bronx,undefined

[8] NY 10458-9993,undefined

[9] USA,undefined

来源：

Monatshefte für Chemie / Chemical Monthly | 2003年 / 134卷

关键词：

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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学科分类号：

摘要：

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.

引用

页码：1099 / 1104

页数：5