Chemical and Pharmaceutical Bulletin
Online ISSN : 1347-5223
Print ISSN : 0009-2363
ISSN-L : 0009-2363
Studies on Pyridazines. XXV. The Ring-opening Reactions of N-Methoxypyridazinium Salts with Nucleophiles
井下田 浩金子 千里土屋 隆
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1975 年 23 巻 11 号 p. 2798-2804

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The reaction of 1-methoxypyridazinium methosulfate (1) with cyanide ion resulted in the ring fission and subsequent elimination of N2 to give the cyano substituted vinyl acetylenes (2 and 3) and 1, 3-butadienes (4). On the other hand, reactions of the salt (1) with hydroxide and dicyanomethyl anion resulted in the similar ring-opening, followed by elimination of the methoxyl group, to give vinyl diazomethanes (6 and 9), which were easily converted into the corresponding pyrazole derivatives (7 and 10) by an intramolecular 1, 3-dipolar cycloaddition. The reaction mechanism is also discussed.
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© The Pharmaceutical Society of Japan
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