The Chemistry of Indoles. XIII. Syntheses of Substituted Indoles carrying an Amino, Nitro, Methoxycarbonyl, or Benzyloxy Group at the 4-Position and Their 1-Hydroxy Derivatives

スポンサーリンク

概要

• 論文の詳細を見る

• Various 1-hydroxyindoles carrying a nitro, methoxycarbonyl, or benzyloxy group at the 4 position were prepared by the controlled reduction of 6-substituted trans-β-dimethylamino-2-nitrostyrenes with either aqueous titanium (III) chloride or zinc in aqueous ammonium chloride. The stability of 4-substituted 1-hydroxyindoles decreased in the following order : 4-nitro-≫4-methoxycarbonyl->4-benzyloxy-1-hydroxyindole. This result clearly indicates that an electron-withdrawing group at the 4-position can stabilize the 1-hydroxyindole structure. It was also found that 4-hydroxy-and 4-benzyloxy-indole were readily accessible by the reduction of 6-benzyloxy-2-nitrophenyl acetaldehyde. A unique route to 4-or 7-aminoindole from cinnoline is also described.

• 公益社団法人日本薬学会の論文
• 1981-03-25

著者

• 井上 里美

  Faculty Of Pharmaceutical Sciences Kanazawa University

• 山田 文夫

  金沢大薬

• 金子 主税

  Faculty Of Pharmaceutical Sciences Kanazawa University

• 染井 正徳

  Faculty of Parmaceutical Sciences, Kanazawa University

• 山田 文夫

  Faculty of Pharmaceutical Sciences, Kanazawa University

• 徳武 昌一

  Faculty of Pharmaceutical Sciences, Kanazawa University

• 金子 主税

  Pharmaceutical Institute Tohoku University

• 徳武 昌一

  Faculty Of Pharmaceutical Sciences Kanazawa University

関連論文

• アミノ酸誘導体に関する研究-6-メトキシメチレンメルドラム酸とアミノ酸誘導体との反応
• A Novel Synthesis of β-Ketothioesters
• A Novel Synthetic Method for Tetronic Acids from 1,3-Dioxin-4-ones via Intra- or Intermolecular Ketene Trapping
• Synthesis of 1,3-Dioxin-4-ones and Their Use in Synthesis. XVIII. : Synthesis of Azetidin-2-ones from 1,3-Dioxin-4-ones via 3-Hydroxycarboxamides
• Studies on Amino Acid Derivatives. IX. : Synthesis of Chiral Penam-3-carboxylic Acid and Its Substituted Derivatives
• REDUCTION OF OXIMES OF α-SUBSTITUTED β-KETOESTERS WITH SODIUM CYANOBOROHYDRIDE : STEREOSELECTIVE SYNTHESIS OF 3,4-CIS-SUBSTITUTED AZETIDIN-2-ONES(Communications to the Editor)
• The Chemistry of Indoles. XLIV. : Synthetic Study Directed toward 3,4,5,6-Tetrahydro-1H-azepino[5,4,3-cd]indoles
• Entstehung von 3-Hydroxyderivaten bei der N-Oxydierung der Chinolinderivate mittels Wasserstoffperoxyds in Eisessig-Losung.
• A Novel Method for Attacking Non-activated C-H Bond and Its Application to the Synthesis of Gibberellin-A_ from Enmein
• Photoaddition of 2-Quinolone and 2-Pyridone Derivatives to Diketene : On the Regioselectivity of the Photoaddition
• A TOTAL AND PRACTICAL SYNTHESIS OF ERGOT ALKALOID, (±)-AURANTIOCLAVINE
• 62 麦角アルカロイド、(±)-clavicipitic acidの5工程全合成(ポスター発表の部)
• THE CHEMISTRY OF 1-HYDROXYINDOLES : SYNTHESES OF METHYL 1-HYDROXYINDOLE-3-ACETATE, N__-B-ACETYL-1-HYDROXY-TRYPTAMINE, (±)- AND (S__-)-1-HYDROXYTRYPTOPHAN DERIVATIVES
• A SIMPLE SYNTHESIS OF THE INDOLE ALKALOID BIPOLARAMIDE AND ITS DERIVATIVES
• 20 タリウムの化学を利用した新反応群の開拓とその天然物合成への応用(口頭発表の部)
• TIN-THALL REACTION, A VERSATILE METHOD FOR CROSS COUPLING TIN COMPOUNDS WITH THALLIUM COMPOUNDS(Communication to the Editor)
• The Chemistry of Indoles. XXXIII. : Substituent Effect in Regioselective Metalation of 3-Indolecarbaldehyde and Syntheses of Indoles Carrying a Carbon Side Chain at the 4-, 5-, 6-, or 7-Position
• The Chemistry of Indoles. XXXII. : A Facile Synthetic Method for 6-Indolecarbaldehyde, 6-Indolemethanol, and 6-Substituted 1-Hydroxyindoles and Its Application for the Synthesis of a Natural Alkaloid, (E)-6-(3-Methylbuta-1,3-dienyl)indole
• BORONATION-THALLATION, A NEW APPROACH TO THE SYNTHESIS OF INDOLES HAVING ARYL AND/OR A HETEROARYL SUBSTITUENT AT THE 4-POSITION
• 57 麦角アルカロイド全合成研究
• SHORT-STEP SYNTHESIS OF THE ERGOT ALKALOIDS, (±)-NORCHANOCLAVINE-I, (±)-CHANOCLAVINE-I, (±)-ISOCHANOCLAVINE-I, AND (±)-AGROCLAVINE
• The Chemistry of Indoles. XXVII. : A Practical Synthesis of the 1-Methoxy Analog of an Ergot Alkaloid, (±)-1-Methoxy-6,7-secoagroclavine
• TOTAL SYNTHESIS OF (±)-PANICULIDINE B
• The Chemistry of Indoles. XXIV. Syntheses of 3-Indoleacetic Acid and 3-Indoleacetonitrile Having a Halogeno Group and a Carbon Functional Group at the 4-Position
• 29 短工程かつ実用的な麦角アルカロイド全合成
• 私と光化学反応
• 創薬と薬の正確・安全な適用を薬学の二大目標とする立場から("薬学の基礎"の概念)
• まず支部例会の充実を(薬学会の総会・分科会制度の是非)
• A PRACTICAL SYNTHESIS OF THE ERGOT ALKALOID (±)-6,7-SECOAGROCLAVINE
• The Chemistry of Indoles. XIII. Syntheses of Substituted Indoles carrying an Amino, Nitro, Methoxycarbonyl, or Benzyloxy Group at the 4-Position and Their 1-Hydroxy Derivatives
• Use of 1,3-Dioxin-4-ones and Related Compounds in Synthesis. XLIV. Asymmetric Aldol Reaction of 4-Trimethylsiloxy-6-methylene-1,3-dioxines : Use of Tartaric Acid-Derived (Acyloxy)borane Complex as the Catalyst
• l-MENTHYL (2S)-2-PHENYL-3-(p-ANISYL)-(5Z)-BENZYLIDENE-4,6-DIOXO-1,3-OXAZINE-2-CARBOXYLATE : A NEW CHIRAL HETERODIENE AND MICHAEL ACCEPTOR
• Synthesis of 1,3-Dioxin-4-ones and Their Use in Synthesis XX. : (6S, 7S, 10R)- and (6R, 7S, 10R)-7-Isopropyl-10-mythyl-4-oxo-1,5-dioxaspiro[5.5]undec-2-enes; Synthesis and Their Use in Enantiomerically Pure Corey Lactone Analogue Synthesis
• Synthesis of 1,3-Dioxin-4-ones and Their Use in Synthesis. XVII. : Chiral Spirocyclic 4-Oxo-1,3-dioxin-5-carboxylates : Asymmetric Synthesis of Carbocyclic C-Nucleoside Precursors
• A NEW METHOD FOR INTRODUCING THE 2,2-DICHLOROETHYL GROUP AT THE 3 POSITION OP THE 2-QUINOLONE SYSTEM, AND THE SYNTHESIS OF DICTAMNINE(Communication to the Editor)
• Cycloadditions in Syntheses. XXXII. Intramolecular Photocycloaddition of 4-(ω-Alkenyloxy)quinolin-2(1H)-one: Synthesis of 2-Substituted Cyclobuta[c]quinolin-3(4H)-ones(Organic,Chemical)
• A NOVEL THREE-CARBON ANNELATION METHOD FOR PYRIDINE DERIVATIVES
• A NOVEL PHOTOCHEMICAL PRENYLATION REACTION OF HETEROAROMATICS INVOLVING AN ENONE FUNCTION IN THEIR RING SYSTEM
• Cycloadditions in Syntheses. VIII. Synthesis of 1,2-Dihydrocyclobuta [c]-pyridine and -quinoline and Their 3-Substituted Derivatives
• 1,2-Dihydrocyclobuta [c] quinoline
• A Photochemical Synthesis of 1,2,3,4,5,6-Hexahydro-1-benzazocine-2,6-diones from 4-Hydroxy-2-quinolones
• The Convenient Synthesis of 25-Hydroxycholesterol
• Synthesis of 1α, 24 (R)- and 1α, 24 (S)-Dihydroxycholesterol from Cholic Acid Derivatives
• Photolysis of 2-(Trifluoromethyl) quinoline 1-Oxides and 1-(Trifluoromethyl) isoquinoline 2-Oxide
• Synthese von Derivaten der Cinchona-Alkaloide. XXXIII. Synthese von 2'-Cyanoderivaten der Alkaloide der Chinin-Reihe
• Uber eine modifizierte Reissert'sche Reaktion in der Chinolin-1-oxid-Reihe.
• Uber eine neue Nitrierung des Chinolin-1-oxides. (4).
• Polarisation der Heterozyklischen Ringe mit aromatischem Charakter. CXXXVII. Bemerkung zur Nitrierung des Pyridin-1-oxydes mittels Acylnitrates und uber 3,5-Dinitropyridin-1-oxyd.
• Uber 2-Hydroxychinolin-1-oxyd.
• Uber eine neue Nitrierung des Chinolin-1-oxydes. (3).
• Nitrierung des 6-Methyl-und 3-Bromchinolin-N-oxydes mit Benzoylnitrat.
• Uber eine neue Nitrierung des Chinolin-N-oxydes. (2).
• Polarisation der heterozyklischen Ringe mit aromatischem Charakter. CXV. Uber eine neue Nitrierung des Chinolin-N-oxydes.
• Titanium (III) Chloride for the Reduction of Heteroaromatic and Aromatic Nitro Compounds
• Studies on Amino Acid Derivatives. V. Synthesis of Pyridobenzazoles
• A SIMPLE METHOD FOR SYNTHESIZING 7-OXO-4-THIA-1-AZABICYCLO [3. 2. 0]-HEPTANE AND ITS 6-METHYL DERIVATIVES FROM ETHYL CYANOACETATE
• Photoaddition of 4(3H)-Quinazolinone Derivatives to Olefins : Effects of the 2-Substituent
• NOVEL METHODS FOR INTRODUCING A TWO-CARBON UNIT AT EITHER THE 3- OR 4-POSITION OF THE ISOQUINOLONE RING BY MEANS OF PHOTO[2+2]CYCLOADDITION REACTION
• Synthesis of 1,3-Dioxin-4-ones and Their Use in Synthesis. XIII. : Synthesis of 5-Halo-1,3-dioxin-4-ones and Their Conversion to 5-Alkyl Derivatives
• Cycloadditions in Syntheses. XXVI. : 1,2-Dihydrocyclobuta[b]-naphthalene-3,8-diones : Synthesis by Photochemical Means and Their Reactions via 2,3-Dimethylene-1,4-dioxo-1,2,3,4-tetrahydronaphthalenes
• Synthesis of 1,3-Dioxin-4-ones and Their Use in Synthesis. XI. : 2,2-Dimethyl-1,3-dioxin-4-one as a Synthetic Equivalent of Formylketene : Synthesis of Heterocyclic Compounds
• Cycloadditions in Syntheses. XXIV. 1,2-Dihydrocyclobut [c] isoquinoline
• Studies on the N-Oxides of π-Deficient N-Heteroaromatics. XXXIV. A Novel Synthesis of Substituted Indoles by Photochemical Ring Contraction of 3,1-Benzoxazepines
• Ring Contraction Reactions of Methyl Quinoline 1-Oxide 5-Carboxylates via the Corresponding Benz [d]-1,3-oxazepines. A Facile Synthesis of Methyl Indole 4-Carboxylate and Its Derivatives
• 3-Sulfolene as an Alternative Reagent for Sulfur Dioxide
• Photochemical Reactions of 6-Cyanophenanthridine 5-Oxide
• Studies on the N-Oxides of π-Deficient N-Heteroaromatics. XXXVI. Photochemical and Thermal Michael Reactions of Alcohols with Methyl 2-Phenyl-3,1-benzoxazepine-5-carboxylate and Its Derivatives
• α, β-不飽和カルボニル基を内蔵する複素芳香環化合物とアルケン類との光2+2付加体におけるC-C結合の開裂反応
• INTRODUCTION OF A FUNCTIONALIZED CARBON CHAIN AT THE 3-POSITION OF 4-METHOXY-2-QUINOLONES VIA PHOTOCHEMICAL 2+2 CYCLOADDITION TO ALKYNES AND THE SYNTHESIS OF (±)-EDULININE
• A METHOD OF SYNTHESIZING 8-OXOPROTOBERBERINE DERIVATIVES INVOLVING A NOVEL PHOTOARYLATION OF 3-CHLORO-1-ISOQUINOLONES
• Intermolecular Photochemical Cycloaddition of 4-Methoxy-2-quinolone with Olefins : A Regioselective Synthesis of 5-Substituted Cyclobuta [c]-2-quinolones
• A Novel Synthesis of Revenine and Related Alkaloids by Means of a Photo-rearrangement Reaction of 4-Alkoxy-2-methylquinoline 1-Oxides
• SYNTHETIC STUDY DIRECTED TOWARD CYCLOPIAZONIC ACID
• The Chemistry of Indoles. XII. A Facile Route to 5-Nitroisocoumarins and Methyl Indole-4-carboxylate

もっと見る 閉じる

スポンサーリンク