Studies on Ketene and Its Derivatives. CIX. Synthesis of naturally Occurring Anthracene-9,10-diones

スポンサーリンク

概要

• 論文の詳細を見る

• The synthesis of naturally occurring anthracene-9,10-diones (12a-c) from ethyl 2-benzyl-4,6-dihydroxybenzoates (7a-d), prepared by the reaction of diketene with ethyl 4-aryl-3-oxobutanoates (6a-d), is described. Reaction of diketene with 6a-d in the presence of sodium hydride in tetrahydrofuran gave 7a-d. Treatment of 7a-d with methyl iodide in the presence of potassium carbonate, followed by ethanolic sodium hydroxide, gave 2-benzyl-4,6-dimethoxybenzoic acids (9a-d). Cyclization of 9a-d with trifluoroacetic acid-trifluoroacetic anhydride gave anthrone derivatives (10a-d) which, without purification, were oxidized with chromium trioxide to give the anthracene-9,10-diones (11a-d). Selective demethylation of 11a-c with boron tribromide gave 12a-c.

• 公益社団法人日本薬学会の論文
• 1982-07-25

著者

• 加藤 鐵三

  Central Research Institute Mect Corporation

• 加藤 鐵三

  Pharmaceutical Institute. Tohoku University

• 片桐 信弥

  Pharmaceutical Institute, Tohoku University

• 中野 潤

  Kaken Pharmaceutical Co. Ltd.

• 中野 潤

  Kakenyaku-kako Kyoto Research Laboratories

• 片桐 信弥

  Health Sci. Univ. Hokkaido Hokkaido Jpn

• 片桐 信弥

  Pharmaceutical Institute Tohoku University

関連論文

• アミノ酸誘導体に関する研究(第3報)アセトアセチルアミノ酸を用いるトリペプチドおよびテトラペプチドの簡易合成
• ケテンおよびその誘導体の研究(第120報)アセトアセチルアミノ酸誘導体を用いるアセチルジペプチドの合成
• Chiral Synthesis of Erythrina Alkaloids. I. Total Synthesis of (+)-Erysotrine via Asymmetric Diels-Alder Reaction under High Pressure
• Cycloadditions in Syntheses. XXXVII. : Syntheses of 6-Trifluoromethyl-1,2,4-triazines and -1,2,4-triazin-5-ones and Their Pericyclic Reactions with Olefins
• Cycloadditions in Syntheses. XXXI. 2+2 Photocycloaddition of 3-Trifluoromethyl Derivatives of Quinoxalin-2(1H)-one and 1,4-Benzoxazin-2-one to Olefins : Effects of the Trifluoromethyl Group(Organic,Chemical)
• DOUBTS ABOUT THE LIBIT'S METHOD FOR THE SYNTHESIS OF THE "COREY"INTERMEDIATE USING PHOTOCYCLOADDITION AS A KEY STEP
• Photoaddition of 2-Quinolone and 2-Pyridone Derivatives to Diketene : On the Regioselectivity of the Photoaddition
• Studies on Ketene and Its Derivatives. CXVI. Some Reactions of 3-Oxocyclobuta[c]quinoline-2-spiro-2'-oxetane : [4+2]Cycloaddition via ortho-Azaquinodimethane
• Synthesis of Ethyl 2-Thioxo (and 2-Methylene) thiazoline-4-acetates
• Studies on Ketene and Its Derivatives. CI. Reaction of Diketene with 4-Amino-methylpyridine 1-Oxides
• 1,3-Oxazine化学の最近の進歩 (ヘテロ環の化学-5-)
• Reaction of Diketene-Acetone Adduct with Enamines, Ketene Acetals, Vinyl Ethers, and β-Diketones
• Studies on Ketene and Its Derivatives. CXVIII. Nickel- or Palladium-Catalyzed Reaction of Diketene with Organometallics. Synthesis of 3-Substituted 3-Butenoic Acids
• STUDIES ON KETENE AND ITS DERIVATIVES. CXV. REACTION OF DIKETENE WITH ORGANOMETALLICS IN THE PRESENCE OF THE NICKEL- OR PALLADIUM-PHOSPHINE COMPLEX
• Syntheses of the Optical Isomers of Befunolol・HCl and Their β-Adrenergic Blocking Activities
• Use of 1,3-Dioxin-4-ones and Related Compounds in Sythesis. XXXVIII. Use of 1,3-Dioxin-4-ones Having a Fluorine or Trifluoromethyl Group at the 5-Position as _π2 Components in [2+2]-Photocycloaddition and Diels-Alder Reactions
• Synthesis of Nucleosides and Their Related Compounds. XII. : Menthyl 2,4-Dioxo-1,3-oxazine-5-carboxylates : New Dienophiles for the Asymmetric Diels-Alder Reaction Directed towards Synthesis of Carbocyclic C-Nucleosides
• Synthesis of 1,3-Dioxin-4-ones and Their Use in Synthesis.XVI. : 4-Oxo-1,3-dioxin-5-carboxylic Acids and Related Compounds : Versatile Synthetic Intermediates for the Synthesis of 6-Unsubstituted Six-Membered Heterocyclic Compunds
• Synthesis of C-Nucleosides via [2+4] Cycloaddition of Ketene Intermediate
• Synthesis of C-Nucleosides by Ring Transformation of 1,3-Oxazine Derivatives
• Studies on Ketene and Its Derivatives. CXXII. Reaction of Haloketenes with 1,3-Diaza-1,3-diene Compounds
• Studies on Ketene and Its Derivatives. CXVII. Reaction of Dichloroketene with Ethyl N-(2-Pyridyl) formimidates
• Synthesis of Imidazo[1,5-a]pyrimidines
• Reaction of β-Aminocrotonamide with N-Acylated Amino Acid Esters to give 2-Acylaminoalkyl-6-methylpyrimidin-4 (3H)-ones and Their Ring Closure with Polyphosphoric Acid (PPA)
• Studies on Ketene and Its Derivatives. CXII. Reaction of Ketene with Schiff Bases to give α-Unsubstituted β-Lactams
• Studies on Ketene and Its Derivatives. CX. Synthesis of 1,3-Dimethoxyfluoren-9-ones
• Studies on Ketene and Its Derivatives. CIX. Synthesis of naturally Occurring Anthracene-9,10-diones
• Ring Transformation of 5-Oxo-4-oxaspiro [2.3] hexanes
• Trichloromethylquinolines : Synthesis and Reaction with Trimethyl Phosphite
• Studies on Ketene and Its Derivatives. XCIV. Reaction of Diketene with Diazoacetone and 2-Diazoesters
• ドクササコの有毒成分とその薬理作用
• Chemical Reactions of Bikaverin
• Studies on Ketene and Its Derivatives. LIII. Reaction of Diketene with Diazoacetophenone and Ethyl Diazoacetate
• Studies on Ketene and Its Derivatives. XLVIII. Reaction of Diketene with Hydroxylamine
• Studies on Ketene and Its Derivatives. XLVII. Reaction of 2-Aminopyridine with Diketene
• Studies on Ketene and Its Derivatives. XLVI. Mass Spectrometric Studies of 3-Acetyl-4-hydroxy-6-methyl-1-pyridyl-2-pyridones and N-Pyridyl-2,6-dimethyl-4-pyrone-3-carboxamides
• A Concise Preparation of Yuehchukene and its Analogues
• Total Synthesis of Yuehchukene
• An Efficient Total Synthesis of Ellipticine
• 新しい反応活性種,ニトロソケテンを経る機能性環状ニトロンの生成と変型アミノ酸合成への展開
• ゴードン会議に参加して 炭素環ヌクレオシドのトピックスを中心に
• 酵素反応への高圧の適用 (特集/超高圧と有機化学)
• SELECTIVE PROTECTION OF THE PRIMARY HYDROXYL GROUPS OF OXETANOCIN A AND CONFORMATIONAL ANALYSIS OF O-PROTECTED OXETANOCIN A
• 新規ヌクレオシド分子の構築--炭素環ヌクレオシドを中心に(新規合成法の開発) (核酸化学の新展開--新しい機能性分子を求めて) -- (新しい構造と機能を有するヌクレオシドの分子設計)
• EXPLANATION FOR STEREOSELECTIVITY OF THS CIS-DIHYDROXYLATION OF CIS-3,5-DISUBSTITUTED CYCLOPENTENES
• Synthesis of Nucleosides and Related Compounds. XXXIV. Synthesis of 5-Isonitroso-1,3-dioxane-4,6-diones and Their Reactions
• Synthesis of Nucleosides and Related Compounds. XXXI. Resolution of 9-[c-4,t-5-Bis(hydroxymethyl)cyclopent-2-en-r-1-yl]-9H-adenine [(±)-BCA] by Means of High-Pressure-Mediated Deamination with Adenosine Deaminase
• 抗HIV剤の創製を目標とした高度に修飾されたヌクレオシドの合成研究
• Synthesis of Nucleosides and Related Compounds. XXVI. The Difference in Effects between High Pressure and LiClO_4 for the Diels-Alder Reaction of Cyclopentadiene with Methylenemalonates or O-Acetylisonitrosomalonates
• The Alkylation of 6-Chloropurine with Alcohols by Mitsunobu Reaction
• Synthesis of Nucleosides and Related Compounds. XXII. Carbocyclic Analogues of Thymidine and Related compounds from 2-Azabicyclo[2.2.1]hept-5-en-3-ones
• 超高圧下の有機反応
• Synthesis of Carbocyclic Nucleosides from 2-Azabicyclo[2.2.1]hept-5-en-3-ones : Sodium Borohydride-Mediated Carbon : Nitrogen Bond Cleavage of Five- and Six-Membered Lactams
• Synthesis of Nucleosides and Related Compounds. XVII. Dialkyl 1,3-Dithiethan- and 1,3-Dithiolan-2-ylidenemalonate S-Oxides : Equivalents to Dialkoxycarbonylketenes
• SYNTHESIS OF 9-(t-2,c-3-DIHYDROXYMETHYL-r-1-CYCLOPROPYL)-9H-ADENINE (A LOWER METHYLENE HOMOLOG OF CARBOCYCLIC OXETANOCIN) AND RELATED COMPOUNDS
• HIGHLY STEREOSELECTIVE SYNTHESIS OF CARBOCYCLIC ANALOGUES OF OXETANOCIN
• Synthesis of Nucleosides and Related Compounds. XIV. : Diels-Alder Reaction of Di-l-menthyl Acetoxymethylenemalonate with Cyclopentadiene : Effects of High-Pressure and Catalysts upon Asymmetric Induction
• Titanium Tetrachloride-Mediated Diels-Alder Reactions of Cyclopentadiene with Di-l-menthyl Methylenemalonate and Its Acetoxy Derivative as New Chiral Dienophiles for Asymmetric Induction
• Synthesis of Isothiourea Derivatives
• SYNTHESIS OF 4-TRIFLUOROMETHYLAZETIDIN-2-ONES BY A NOVEL 2+2 PHOTOCYCLOADDITION OF 3-TRIFLUOROMETHYL-QUINOXALIN-2-ONE OR-1,4-BENZOXAZIN-2-ONE TO KETENE
• Photoaddition of 4(3H)-Quinazolinone Derivatives to Olefins : Effects of the 2-Substituent
• Synthesis of β-Ketocarboxamide Derivatives Using 2,2-Dimethyl-2H, 4H-1,3-dioxin-4-ones
• Reaction of 2,2-Dimethyl-1,3-dioxin-4-ones with Imines, Carbodiimides, and Isocyanates
• Reaction of 2,2,6-Trimethyl-1,3-dioxin-4-one with Imines
• Synthesis of 1,3-Dioxin-4-one Derivatives
• Novel Annelation Method to Pyridine and Isoquinoline by Photochemical Means
• Photochemical [2+2] Cycloreversion Reactions of 1,2,2a, 8b-Tetrahydrocyclobuta [c] isoquinolin-4 (3H)-ones
• 新規 2-polyfluorophenylbenzazole 誘導体の合成と殺ダニ活性
• A206 新規ベンズアゾール系化合物の合成とその殺ダニ活性
• Synthesis and Antiallergic Activity of Novel Azaazulene Derivatives
• Studies on Ketene and Its Derivatives. CXIII. Reaction of Dichloroketene with Aromatic Amine N-Oxides
• Reaction of 2,2,6-Trimethyl-1,3-dioxin-4-one with Isoquinolinium and Pyridinium Ylides
• ヌクレオシドの新しい高立体選択的合成法 : 新しいジェノフィルの創製と還元条件下での逆アルドール反応の利用
• FACILE SYNTHESIS OF THE CARBOCYCLIC ANALOGUE OF β-RIBOFURANOSYL-MALONATE, NEW SYNTHON FOR CARBOCYCLIC C-NUCLEOSIDE FORMATION BY RETROGRADE ALDOL C-C BOND FISSION
• 光化学的周辺環状反応を用いる生理活性化合物の合成
• Studies on Ketene and Its Derivatives. XXXIX. Reaction of Diketene with Semicarbazone
• Studies on Ketene and Its Derivatives. XXXVIII. Reaction of Diketene with Phenylhydrazones to give 4-Acetyl-2-phenylpyrazolidin-3-ones

もっと見る 閉じる

スポンサーリンク