The Synthesis of 7-Isopropyl-2,4-dimethylazulene (Se-Guaiazulene) from 4-Isopropyltropolone

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概要

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• 7-Isopropyl-2,4-dimethylazulene (Se-guaiazulene) (I) was synthesized from 4-isopropyl-7-methyltropolone (II), which had itself been derived from 4-isopropyltropolone. The tropolone, II, was then converted to 3-acetyl-5-isopropyl-8-methyl-2<I>H</I>-cyclohepta[<I>b</I>]furan-2-one (VI) <I>via</I> the <I>p</I>-tolylsulfonyloxytropone derivative derived from II. The application of the azulene synthesis to VI gave 3-cyano-7-isopropyl-2,4-dimethylazulene-1-carboxylic acid (VII), from which I was obtained by the removal of the carboxyl and cyano groups.

• 公益社団法人 日本化学会の論文

著者

• Takase Kahei

  Department Of Chemistry Faculty Of Science Tohoku University

• Nozoe Tetsuo

  Department of Chemistry Faculty of Science Tohoku University

• Fukuda Satoko

  Department of Chemistry, Faculty of Science, Tohoku University

関連論文

• The Synthesis and Properties of Cyclopent[a]azulen-3(H)-one
• The Synthesis of Azulene Derivatives from Troponoids
• Synthesis of 2-Substituted Azulenes by Nucleophilic Substitution Reactions of 2-Haloazulene Derivatives
• 2-Phenylthiazolo[4,5-b]tropones
• Syntheses of Benzo[b]tropothiazine and its Derivatives
• Reaction of Tropylium Ion with Tropolone
• Reaction of Troponoids and Organometallic Compounds. VI. Reaction of Tropone with Grignard Reagents
• The Reaction of 5- and 6-Acetylazulene Derivatives with Hydrazines. The Formation of Azuleno[4,3-f]pyrazoles
• 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.
• Some Oxidation and Reduction Products of 4-Acetyltropolone and Its Methyl Ethers
• The reaction of 2-chloroazulene derivatives with lithium acetylide in liquid ammonia.
• Studies on the syntheses of sesquiterpene lactones. III. Improved synthesis of vulgarin.
• A facile synthesis of colchiceine analogues (4-(1-acetamido-3-arylpropyl)tropolones).
• The synthesis of 2-styrylazulene and its derivatives by the condensation of 2-methylazulene derivatives with benzaldehydes.
• Synthesis of 2-formylazulene and its derivatives by oxidative cleavage of 2-styrylazulenes.
• The total syntheses of chamaecynone, isochamaecynone, and dihydroisochamaecynone.
• The Reaction of 3-(ω-EthoxycarbonyIacetyl)-2H-cyclohepta[b]furan-2-one with Active Methylene Compounds
• Base-catalyzed 1-3 Prototropic Isomerization of Cycloheptatrienes
• p-(3,4-Diphenyl-1,3-cyclopentadien-1-yl)phenyltropylium Perchlorate. An Intermediate in the Synthesis of [5.6.7]Quinarene System
• The total syntheses of (-)-occidentalol and its C7-epimer. The stereochemical assignment of (+)-occidentalol.
• Structure of reaction products of 5-nitrosotropolone and arylamine.
• The total synthesis of hydroxyisochamaecynone and its stereochemical assignment.
• A convenient synthesis of 4- and 5-acetyltropolone.
• Synthesis and the spectral analysis of 4- and 6-(1-acetamido-3-(3,4,5-trimethoxyphenyl)propyl)-2-methoxytropones (B-ring-open analogues of colchicine).
• The nucleophilic displacement reactions of 8-chloro- and 2,8-dichloro-3-phenyl-1-azaazulenes.
• Syntheses of Indolo[2,3-b]tropones and Benzo[b]-1-azaazulenes from 2-Hydrazinotropones
• The Synthesis of Azulene Derivatives Condensed with Several Heterocycles
• Some Electrophilic Substitution Reactions of 2-Hydroxyazulene Derivatives
• Reactions of 1-Azaazulan-2-one and Its 3-Substituted Derivatives
• The Diazotization of 2-Aminoazulene Derivatives. The Formation of 2-Diazo-2,6-azulenoquinone Derivatives
• Application of the Mannich Reaction to 1-Azaazulan-2-one. Syntheses of Seven-Membered Analogues of Tryptophan and Related Compounds
• The Bromination of 2-Methoxytropone and Its Bromo Derivatives
• The Synthesis of 1-Phenylazulene and 2-Phenylazulene from the Troponoid Compound
• The Synthesis of 7-Isopropyl-2,4-dimethylazulene (Se-Guaiazulene) from 4-Isopropyltropolone
• Studies on the syntheses of sesquiterpene lactones. I. Chemical transformation of .ALPHA.-santonin into vulgarin, C4-epivulgarin, and arglanine.
• Synthesis of 1,1'-, 2,2'-, 1,2'-, and 2,6'-biazulenes and their derivatives by Ullmann reaction.

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