Syntheses of Indolo[2,3-<I>b</I>]tropones and Benzo[<I>b</I>]-1-azaazulenes from 2-Hydrazinotropones

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概要

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• The application of Fischer's indole synthesis to cyclohexanone 2-troponylhydrazone gave 1,2,3,4-tetrahydroindolo[2,3-<I>b</I>]tropone (II), which was then dehydrogenated to indolo[2,3-<I>b</I>]tropone (III). 8-, 10-Isopropyl-, and 7-bromoindolo[2,3-<I>b</I>]tropone (XIIa–c) were also obtained by a similar method. The treatment of 2-troponylhydrazones of cycloheptanone and <I>N</I>-benzylpiperidone with dilute sulfuric acid or PPA gave 2,3-pentamethylenepyrrolo[2,3-<I>b</I>]tropone (XIII) and 2-benzyl-1,2,3,4-tetrahydrocyclohept[<I>b</I>]pyrido[3,4-<I>d</I>]pyrrol-6(5H)-one (XIV) respectively. The reaction of III with phosphoryl chloride or thionyl chloride yielded 8-chlorobenzo[<I>b</I>]-1-azaazulene (XV), which was subsequently converted into a hydrazino derivative (XVI). The oxidative decomposition of XVI with copper sulfate in acetic acid afforded benzo[<I>b</I>]-1-azaazulene (XVII).

• 公益社団法人 日本化学会の論文

著者

• Fujimori Kunihide

  Department Of Chemistry Faculty Of Science Shinshu University

• Nozoe Tetsuo

  Department of Chemistry Faculty of Science Tohoku University

• Yamane Kameji

  Department of Chemistry, Faculty of Science, Shinshu University

• Sin Je-Kyun

  Department of Chemistry, Faculty of Science, Tohoku University

関連論文

• Synthesis, Characterization, and Antipeptic Activity of a Novel Surfactant Having an Azulene Moiety
• 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
• Some Oxidation and Reduction Products of 4-Acetyltropolone and Its Methyl Ethers
• A facile synthesis of colchiceine analogues (4-(1-acetamido-3-arylpropyl)tropolones).
• 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
• Structure of reaction products of 5-nitrosotropolone and arylamine.
• 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).
• A convenient synthesis of azuleno(2,1-b)thiophene.
• A convenient synthesis of indolotropones and 6-substituted 5-azabenz(b)azulenes.
• Syntheses of Benzo[5,6]cyclohept[1,2-b]indol-6-ones
• The nucleophilic displacement reactions of 8-chloro- and 2,8-dichloro-3-phenyl-1-azaazulenes.
• Synthesis of 2-methylazuleno(1,2-d)thiazoles.
• 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
• Syntheses of Pyrrolotropone Derivatives from Benzocycloheptene-5,6-dione Monoarylhydrazones. II. Syntheses of Benzo[5,6]cyclohept[l,2-b]-indole-6,11,12-triones
• 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

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