Reactivity of Isocoumarins. III. Reaction of 1-Ethoxyisochroman with Benzylamines

スポンサーリンク

概要

• 論文の詳細を見る

• As a part of our studies on the reactions of 1-ethoxyisochroman (1) with nucleophilic reagents, the reaction of 1 with benzylamines was examined. Heating of 1 with benzylamine or its derivatives having an electron-releasing or-attracting group at the 4-position gave 1-benzylaminoisochroman (2) or the corresponding 1-(4-substituted benzylamino) isochromans (6 and 7). Pyrolysis of 2,6,and 7 gave 4-benzylisoquinoline (3) and 4-(4-substituted benzyl)-isoquinolines (8 and 9), respectively. Compound 3 was also obtained by heating 2-(2-hydroxyethyl) benzaldehyde with benzylamine, or by heating 2-vinylbenzylidenebenzylamine (4), while the reaction of 1 with N-methylbenzylamine afforded 1-(N-methylbenzylamino) isochroman (5) and did not give the 4-benzylisoquinoline derivative at all. The reaction mechanism giving 4-benzylisoquinolines is proposed to be as shown in Chart 3.

• 公益社団法人日本薬学会の論文
• 1981-03-25

著者

• 大和 正利

  Faculty Of Pharmaceutical Sciences Okayama University

• 小林 利雄

  Faculty of Pharmaceutical Sciences, Kyushu University

• 石川 忠興

  Faculty Of Pharmaceutical Sciences Okayama University

• 小林 利雄

  Faculty Of Pharmaceutical Sciences Kyushu University

関連論文

• Alkoxycarbonylmethylation of(3R, 10bS)-3-Phenyl-2,3,5,6-tetrahydro-10bH-oxazolo[2,3-a]isoquinoline
• Synthesis and Antitumor Activity of Fused Quinoline Derivatives. III. Novel N-Glycosylamino-indolo[3,2-b]quinolines
• Synthesis and Antitumor Activity of Fused Quinoline Derivatives. II. Novel 4- and 7-Hydroxyindolo-[3,2-b]quinolines
• Asymmetric syntheses of 1-Alkyltetrahydro-β-carbolines and a 9-Thio Analogue
• SYNTHESIS AND ANTITUMOR ACTIVITY OF 7-(N-GLYCOSYLAMINO)-INDOLO[3,2-b]QUINOLINES
• Asymmetric Synthesis of 1-Benzyltetrahydroisoquinolines Using Chiral Oxazolo[2,3-α]tetrahydro-isoquinolines
• Synthesis and Antitumor Activity of Fused Quinoline Derivatives
• The Wittig Reaction of Benzofuran-2,3-diones
• Syntheses and Antifungal Activities of dl-Griseofulvin and Its Congeners. I
• A Practical Synthetic Method for β-Ketoesters from Ketones
• One-Flask Synthesis of Sulfides from Alcohols and Alkyl Halides Using Benzoxazoline-2-thione
• A New Method for the Preparation of 2-Alkoxybenzoxazoles
• Synthesis of 3-Substituted Benzoxazoline-2-thiones
• Reaction of Benzoxazoline-2-thiones with Alkyl Halides
• Reaction of Anthranilamides with Levulinic Acids. Synthesis of 2,3,3a, 4-Tetrahydropyrrolo [2,1-b] quinazoline-1,9-diones
• Reaction of 1,2,3,4-Tetrahydroquinazolin-4-ones with Acid Anhydride. IV
• Reaction of 1,2,3,4-Tetrahydroquinazolin-4-ones with Acid Anhydride. III
• Reaction of 1,2,3,4-Tetrahydroquinazolin-4-ones with Acid Anhydride. II
• THE SYNTHESIS AND ANTITUMOR ACTIVITIES OF TROPOLONE AND 8-HYDROXYQUINOLINE DERIVATIVES
• Polycyclic N-Hetero Compounds. VI. Synthesis of 11,13,15-Triazasteroidal Compounds and Correction of the Structures of Its Intermediates
• Syntheses of 3-Substituted 1-Methyl-6-phenylpyrimido[5,4-e]-1,2,4-triazine-5,7(1H, 6H)-diones (6-Phenyl Analogs of Toxoflavin) and Their 4-Oxides, and Evaluation of Antimicrobial Activity of Toxoflavins and Their Analogs
• Condensation of Diethyl Acetonedicarboxylate. II
• Condensation of Diethyl Acetonedicarboxylate. I
• Chemical Structure and Sweet Taste of Isocoumarin and Related Compounds. VI
• Synthesis of 7-Fluoro-B-homo-19-norcholest-5 (10)-en-3β-ol Acetate
• Synthesis of 6β-[^I](2'-Iodo)ethyl-19-norcholest-5(10)-en-3β-ol and Its Tissue Distribution in Mice(Medicinal Chemistry,Chemical)
• Carbamoylation using the CO-containing Copper Complex derived from Lithium N-Methylanilide
• Polycyclic N-Hetero Compounds. XVI. Reactions of Benzyl Ketones with Formamide or Acetamide
• Benzylcarbonyl化合物とFormamideとの反応.VIII.m-位にMethyl基を有するα-Acylphenylacetonitrileの反応
• Polycyclic N-Hetero Compounds. VIII. Reactions of Ketones with Trisformylaminomethane
• Polycyclic N-Hetero Compounds. VII. Reactions of Benzyl Ketones with Formamide XI
• Reactivity of Isocoumarins. I. Effect of a Neighboring Hydroxyl Group on the Reduction of the Lactone Carbonyl Group
• Photochemical Reaction of Isocoumarin and Related Compounds
• Polycyclic N-Hetero Compounds. XVII. Reactions of Heterocyclic Active Methyl Group with Formamide or Trisformylaminomethane
• Polycyclic N-Hetero Compounds. XV. The Vilsmeier Reaction of Phenylacetonitriles. II
• Benzylcarbonyl化合物とFormamideとの反応(第9報)α-Acyl-5,6,7,8-tetrahydro-2-naphthylacetonitrileとの反応
• Benzylcarbonyl化合物とFormamideとの反応(第10報)α-Acyl-α-naphthylacetonitrileとの反応
• 1,3,10-Triazaphenanthreneの合成(第1報)
• Benzylcarbonyl化合物とFormamideとの反応(第7報) : Desoxybenzoinの反応
• Benzylcarbonyl化合物とFormamideとの反応(第6報) : Isoquinoline誘導体の生成
• Benzylcarbonyl化合物とFormamideとの反応(第5報) : α-Acyl-3,4-dimethoxyphenylacetonitrileとの反応
• Benzylcarbonyl化合物とFormamideとの反応(第4報)
• Synthesis and Structure-Activity Relationship of Spiro [isochroman-piperidine] Analogs for Inhibition of Histamine Release. IV.
• Synthesis and Structure-Activity Relationship of Spiro [isochroman-piperidine] Analogs for Inhibition of Histamine Release. III
• Diphenylethane系化合物の立体構造
• Chemical Structure and Sweet Taste of Isocoumarin and Related Compounds. IX
• Chemical Structure and Sweet Taste of Isocoumarin and Related Compounds. VII
• Isocoumarin誘導体および関連化合物の呈する甘味と化学構造について(第5報)
• Chemical Structure and Sweet Taste of Isocoumarins and Related Compounds
• Isocoumarin誘導体および関連化合物の呈する甘味と化学構造について(第4報)
• Chemical Structure and Sweet Taste of Isocoumarins and Related Compounds. X. Syntheses of Sweet 5-Hydroxyflavanones and Related Dihydrochalcones
• Polycyclic N-Hetero Compounds. XIV. Reactions of Methylpyridines with Formamide
• Chemical Structure and Sweet Taste of Isocoumarins and Related Compounds Synthesis of 5-Hydroxyflavanones and Related Dihydrochalcones
• Polycyclic N-Hetero Compounds. XIII. Reactions of Pyridine N-Oxides with Formamide
• Chemical Structure and Sweet Taste of Isocoumarin and Related Compounds. VIII
• Polycyclic N-Hetero Compounds. XII. Reactions of Dihydroxynaphthalenes with Formamide or Trisformylaminomethane
• Polycyclic N-Hetero Compounds. XI. The Modified Vilsmeier Reaction of 4-Alkylpyrimidines
• Polycyclic N-Hetero Compounds. X. Reactions of 1,3-Cyclohexanedione and Its Dimer with Formamide or Trisformylaminomethane
• Polycyclic N-Hetero Compounds. IX. Reactions of Tetralones with Formamide or Trisformylaminomethane
• Synthesis and Structure-Activity Relationship of Spiro [isochroman-piperidine] Analogs for Inhibition of Histamine Release. II
• Synthesis and Antiulcer Activity of (Isochroman-1-yl)alkylamines. II
• Synthesis and Antiulcer Activity of (Isochroman-1-yl)alkylamines. I
• ANTITUMOR ACTIVITY OF ISOCHROMANYLTROPOLONES
• Synthesis and Biological Activity of Spiro [isocoumarin-piperidines] and Reltaed Compounds. I
• Polycyclic N-Hetero Compounds. V. A Novel Synthesis of Isoquinoline by the Vilsmeier Reaction of Phenylacetonitriles
• Polycyclic N-Hetero Compounds. III. Synthesis of 1,3,10-Triazaphenanthrenes
• Reactivity of Isocoumarins. IV. Reaction of 1-Ethoxyisochroman with Nucleophilic Reagents
• Condensation of Diethyl Acetonedicarboxylate. IV. Regioselective Reaction of Diethyl Acetonedicarboxylate-magnesium Complex
• Condensation of Diethyl Acetonedicarboxylate. III. Isolation and Acylation of Diethyl Acetonedicarboxylate-Magnesium Complex
• Synthesis of a Griseofulvin Analogue
• Reaction of Spiro[piperidine-4,2'-(1', 2', 3', 4'-tetrahydroquinazolin)]-4'-ones with Acid Anhydrides
• 生理活性を有するIsocoumarin誘導体の合成(第1報) : 3,4-Dihydroisocoumarin類の甘味と化学構造について
• Reactivity of Isocoumarins. III. Reaction of 1-Ethoxyisochroman with Benzylamines
• Reactivity of Isocoumarins. II. Reaction of 1-Ethoxyisochroman with Nucleophilic Reagents
• Synthesis of dl-Agrimonolide (Constituent of Rhizome of Agrimonia pilosa LEDEB)
• 生理活性を有するIsocoumarin誘導体の合成(第3報)3,4-Dihydroiso-coumarin類の甘味と化学構造について
• 生理活性を有するIsocoumarin誘導体の合成(第2報)3,4-Dihydroisocoumarin類の甘味と化学構造について
• Reactivity of Isocoumarins. V. Reaction of 1-Ethoxyisochroman with Active Methylene Compounds

もっと見る 閉じる

スポンサーリンク