Acid-catalyzed Cyclization of 3-Acetyl-3-(3,4-dimethoxyphenyl) adiponitrile
スポンサーリンク
概要
- 論文の詳細を見る
Hydrolytic cyclization of 3-acetyl-3-(3,4-dimethoxyphenyl) adiponitrile (V) in 65% sulfuric acid at 140° was found to yield 3a-(3,4-dimethoxyphenyl)-2,3,3a, 4,5,6-hexahydroindol-2,6-dione (VI), whose structure was confirmed by spectral properties and transformation into dl-mesembrane (=3a-(3,4-dimethoxyphenyl)-1-methylperhydroindol) (XI). Reactions of V in 65% sulfuric acid at room temperature yielded five products, XIII, XIV, XV, XVI and XVII as intermediates of this cyclization reaction, all of which were converted to the final cyclization product (VI) by heating to 140°in the acid. Possible reaction mechanisms of the formation of VI and the intermediates were proposed. An alternate synthesis of VI from 3,4-dimethoxyphenyl acetone via methyl 3-(2-cyanoethyl)-3-(3,4-dimethoxyphenyl) levulinate (XIX) was also described.
- 社団法人日本薬学会の論文
- 1970-02-25
著者
-
大石 篤郎
Organic Chemistry Research Laboratory, Tanabe Seiyaku Co., Ltd.
-
大石 篤郎
Organic Chemistry Research Laboratory Tanabe Seiyaku Co. Ltd.
-
釘田 博至
Organic Chemistry Research Laboratory, Tanabe Seiyaku Co., Ltd.
-
釘田 博至
Organic Chemistry Research Laboratory Tanabe Seiyaku Co. Ltd.
関連論文
- Synthesis of 1,2,3,4-Tetrahydro-β-carboline Derivatives as Hepatoprotective Agents. I. Dithiocarbamates of Several α-Amino Acids(Medicinal Chemistry,Chemical)
- Synthesis of 3,4-Dihydro- and 1,2,3,4-Tetrahydroisoquinolines
- A New Method for the Preparation of 3,4-Dihydro- and 1,2,3,4-Tetrahydro-β-carbolines
- A NEW METHOD FOR THE PREPARATION OF 3,4-DIHYDRO AND 1,2,3,4-TETRAHYDRO-β-CARBOLINES
- Syntheses of Substituted L- and D-Tryptophans
- A NEW METHOD FOR THE PREPARATION OF 3,4-DIHYDRO-β-CARBOLINES
- A New Enantioselective Synthesis of (2R, 3S)-3-(4-Methoxyphenyl)glycidic Ester via the Enzymatic Hydrolysis of erythro-N-Acetyl-β-(4-methoxyphenyl)serine
- A New Synthetic Route to 1,5-Benzothiazepines. Synthesis of Derivatives of Diltiazem
- (-)-R-1-(4-Hydroxyphenyl)-2-[(3,4-dimethoxyphenethyl)amino]ethanol (Denopamine)の合成と絶対配置
- Amino Acids and Peptides. XXIII. An Asymmetric Synthesis of (R)-(-)-Laudanosine from L-3-(3,4-Dihydroxyphenyl) alanine
- Syntheses of Hexahydroindole-2,6-diones and 15,16-Dimethoxyerythrinane-3,8-dione
- Synthesis of Octahydroindole Derivatives
- Synthesis of dl-Mesembrine and Its trans Isomer
- Acid-catalyzed Cyclization of 3-Acetyl-3-(3,4-dimethoxyphenyl) adiponitrile
- Synthesis of the Optically Active trans-Isomers of Diltiazem and Their Cardiovascular Effects and Ca-Antagonistic Activity
- Synthesis of 1,5-Benzothiazepine Derivatives. III
- Synthesis of 1,5-Benzothiazepine Derivatives. II
- Synthesis of 1,5-Benzothiazepine Derivatives. I
- Synthesis of B/C trans-Fused Morphine Structures. VI. Mass Spectrum, Optical Rotatory Dispersion and Circular Dichroism of B/C trans-Morphine Derivatives
- Synthesis of B/C trans-Fused Morphine Structures. IV. Synthesis of B/C trans-Isomorphine
- Synthesis of a B/C trans-fused Morphine Structure
- Benzoisogranatanine Derivatives. I. Synthesis of 2'-Hydroxy-5-alkyl-6,7-benzoisogranatanines.