Reactions of 3-(2-methyl-1,3-dioxolan-2-yl)tropolone methyl ethers with hydrazines, thiourea, guanidine, and amidines.
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概要
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3-(2-Methyl-1,3-dioxolan-2-yl)tropolone, prepared from 3-acetyltropolone, was methylated with diazomethane to afford 2-methoxy-3-(2-methyl-1,3-dioxolan-2-yl)tropone (<B>3a</B>) and 2-methoxy-7-(2-methyl-1,3-dioxolan-2-yl)tropone (<B>3b</B>). The methyl ether <B>3a</B> reacted with hydrazine to afford 2-hydrazono-3-(2-methyl-1,3-dioxolan-2-yl)-3,5-cycloheptadien-1-one and 3-methyl-1,8-dihydrocycloheptapyrazol-8-one. The reaction with methylhydrazine afforded 3-(2-methyl-1,3-dioxolan-2-yl)-2-methylhydrazono-3,5-cycloheptadien-1-one and 1,3-and 2,3-dimethyl-dihydrocycloheptapyrazol-8-ones. Another methyl ether <B>3b</B> reacted with hydrazine to afford 2-hydrazino-7-(2-methyl-1,3-dioxolan-2-yl)tropone, while the reaction with methylhydrazine gave 2-(2-methyl-1,3-dioxolan-2-yl)-7-(2-methylhydrazino)tropone, 2-(2-methyl-1,3-dioxolan-2-yl)-7-(1-methylhydrazino)tropone, and 1,3-dimethyl-8-methylhydrazono-1,8-dihydrocycloheptapyrazole. On the other hand, the methyl ether <B>3a</B> reacted with guanidine, acetamidine, and benzamidine to give 4-(2-methyl-1,3-dioxolan-2-yl)-2-amino-, 2-methyl-, and 2-phenylcycloheptimidazole, respectively. The reaction of the methyl ether <B>3b</B> also gave the same products. The reaction of <B>3b</B> with thiourea afforded 2-mercapto-4-(2-methyl-1,3-dioxolan-2-yl)cycloheptimidazole but <B>3a</B> resulted in the rearrangement to ethyl 2-(2-methyl-1,3-dioxolan-2-yl)benzoate.
- 公益社団法人 日本化学会の論文
著者
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IMAFUKU Kimiaki
Department of Chemistry, Faculty of Science, Kumamoto University
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Kikuchi Yosuke
Department of Chemistry, Faculty of Science, Kumamoto University
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Yin Bing-Zhu
Department of Chemistry, Faculty of Science, Kumamoto University
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