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KMID : 0370220140580060371
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Yakhak Hoeji
2014 Volume.58 No. 6 p.371 ~ p.377
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Thiolation of Asymmetry Pyridazines; Synthesis of a Regioisomer of New Methylpyridazine
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Park Hae-Sun
Park Myung-Sook
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Abstract
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A new series of 3-alkylthio-6-allylthio-4(or 5)-methylpyridazines (6a-e)-(7a-e) was synthesized from citraconic anhydride (1) for development of candidates possessing anticancer activity. The process involves the formation of pyridazine ring, dichlorination, monoallythiolation, and further another alkylthiolation. Compounds 6a-e, and 7a-e were prepared from 6-allylthio-3-chloro-4-methylpyridazine (4) or 6-allylthio-3-chloro-5-methylpyridazine (5) via nucleophilic substitution reaction with alkylthiol anion as nucleophile. Intermediates 4, and 5 could be converted to target pyridazines 6a-e, and 7a-e using 1~1.5 equivalent of alkylthiol at reflux temperature in methanol in the presence of sodium hydroxide. The structures of the synthetic compounds were characterized using NMR, IR, and GC-MS analyses.
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KEYWORD
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diallyl disulfide, asymmetry pyridazine, methylpyridazines, alkylthiolation, regioisomer
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