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KMID : 0370220120560060390
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Yakhak Hoeji
2012 Volume.56 No. 6 p.390 ~ p.394
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Oxidation of Pyridazinyl Sulfides: Synthesis of New Pyridazinyl Sulfoxides and Pyridazinyl Sulfones with Aqueous Hydrogen Peroxide
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Park Eun-Hee
Park Myung-Sook
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Abstract
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A series of new pyridazinyl sulfoxides 3a~e and pyridazinyl sulfones 4a were synthesized for development of candidates to retain anticancer activity. The utility of sulfoxides and sulfones in both laboratory and industrial practice was quickly recognized, and these species have been extensively utilized, including as pharmaceutical intermediates and anticancer agents. Alkylthiopyridazines 2a~e were prepared from the 3,6-dichloropyridazine using allylthiolation with alkyl mercaptan. Sulfides could be oxidized to sulfoxides or sulfones using 1~3 equivalents of hydrogen peroxide as an oxidant. The oxidation of sulfoxides to sulfones was also accomplished with aqueous hydrogen peroxide. Formation of 3a~e and 4a was undertaken with stirring using 35% hydrogen peroxide at room temperature in acetic acid for 18~72 h. Synthetic compounds were identified using NMR spectrum.
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KEYWORD
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pyridazinyl sulfides, pyridazinyl sulfoxides, pyridazinyl sulfones, oxidation, hydrogen peroxide
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