Synthesis and oxidative cyclization of 3-(1-cycloalkenyl)tropolones.
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概要
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3-(1-Cyclopentenyl)-, 3-(1-cyclohexenyl)-, and 3-(1-cycloheptenyl)tropolones (<B>3a</B>, <B>3b</B>, and <B>3c</B>) were prepared by the hydrolysis of cycloadducts of dichloroketene to cyclopentylidene-, cyclohexylidene-, and cycloheptylidenecyclopentadiene, respectively. Compound <B>3a</B> was oxidized with performic acid to give 1,2,3,5-tetrahydrocyclohepta[<I>b</I>]cyclopenta[<I>d</I>]furan-5-one and 3-(2-oxocyclopentyl)tropolone. Oxidation of <B>3b</B> and <B>3c</B> gave 1,2,3,4-tetrahydro-6<I>H</I>-cyclohepta[<I>b</I>]benzofuran-6-one (<B>4b</B>) and 5,7,8,9,10,11-hexahydrodicyclohepta[<I>b</I>,<I>d</I>]furan-5-one, respectively. Dehydrogenation of <B>4b</B> with palladium catalyst gave 6<I>H</I>-cyclohepta[<I>b</I>]benzofuran-6-one.
- 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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Inoue Kyoko
Department of Chemistry, Faculty of Science, Kumamoto University
関連論文
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- Synthesis and reactions of 2-arylhydrazinotropones. II. Synthesis of 5-aryltropolones and B-ring-open colchicine analogues via benzidine type rearrangement of 2-(2-arylhydrazino)tropones.
- Reactions of 3-acetyltropolone and its methyl ethers with methylhydrazine.
- Substituent effect on the dissociation constants of 5-(substituted styryl)-2-aminotropones.
- Rearrangements in the Palladium-Catalyzed Dehydrogenation of Cyclohexylphenols to Phenylphenols
- Substituent effects on 6-substituted 3-hydroxy-1-methyl-4-pyridones.
- Reactions of 3-(2-methyl-1,3-dioxolan-2-yl)tropolone methyl ethers with hydrazines, thiourea, guanidine, and amidines.
- A convenient synthesis of 3-aminotropolone and its reactions with orthoesters. Formation of 8H-cyclohept(d)oxazol-8-ones.
- Reactions of 3-acetyltropolone and its methyl ethers with hydrazine.
- Synthesis and oxidative cyclization of 3-(1-cycloalkenyl)tropolones.
- Dehydrogenation of 2-(1-Cyclohexenyl)cyclohexanone with Palladium Catalyst
- Substituent effects on tautomerism of 4-pyridinethiones.
- Tautomerism of 4-pyridones.
- Reactions of 4H-pyran-4-thiones with ammonia, hydrazine, and guanidine.
- Structure of 5-hydroxy-2-hydroxymethyl-4-pyridones.
- Synthesis of 5-(substituted styryl)-2-aminotropones.
- Cyclodehydrogenation of 3-cinnamoyltropolones with 2,3-dichloro-5,6-dicyanobenzoquinone.
- Substituent effects on the dissociation constants of 1-aryl-5-hydroxy-2-hydroxymethyl-4-pyridones.
- Reactions of 3-acetyltropolone methyl ethers with 1,2-cyclohexanediamine.
- Oxidative cyclization of 3-(3-heterocycle-substituted 2-propenoyl)tropolones.
- Reactions of 3-acetyltropolone and its methyl ethers with o-aminophenol.
- Substituent effects on dissociation constants of trans-3-hydroxy-6-styryl-4-pyrones.