5-Arylidene 1,3-Dimethylbarbituric Acid Derivatives, Mild Organic Oxidants for Allylic and Benzylic Alcohols

スポンサーリンク

概要

• 論文の詳細を見る

• Various 5-arylidene 1,3-dimethylbarbituric acid derivatives and closely related compounds were synthesized as models of redox coenzymes and used for oxidation of alcohols.Under mild neutral conditions, 5-arylidene 1,3-dimithylbarbituric acid derivatives, especially those having an electron-withdrawing group on the aromatic ring, effectively oxidized allylic and benzylic alcohols to the corresponding carbonyl compounds. The relationship between the oxidizing ability and the structure of the oxidant (coenzyme model) was investigated and it was found that the electron density on the carbon-carbon double bond is a critical factor for the oxidation. In the case of the deuterium-labeled compound, the observed value of normal and primary isotope effect was 3.3 and so it was concluded that mechanism of this oxidation mainly involves the hydride transfer from the alcohol. An electrochemical investigation was also carried out and the redox potentials of the coenzyme models, 5-arylidene 1,3-dimethylbarbituric acid derivatives and related compounds, were measured.

• 公益社団法人日本薬学会の論文
• 1988-01-25

著者

• 米田 文郎

  Faculty of Pharmaceutical Sciences, Kyoto University

• 田中 圭

  Faculty Of Pharmaceutical Sciences Kyoto University

• 田中 圭

  静岡県大 薬

• 陳 星

  Faculty Of Pharmaceutical Sciences Kyoto University

• 木村 禎治

  Faculty of Pharmaceutical Sciences, Kyoto University

• 米田 文郎

  Faculty Of Pharmaceutical Sciences Kyoto University

• 木村 禎治

  Faculty Of Pharmaceutical Sciences Kyoto University

• 田中 圭

  京都大学薬学部

• 田中 圭

  Faculty of Eng., Oita Univ.

関連論文

• An Efficient Method for Preparing gem-Dimethylcyclopropanes from gem-Dibromocyclopropanes(Organic,Chemical)
• Reaction of 8,8-DibromobicycJo[5.1.0]octanes with Higher-Order Organocuprates(Organic,Chemical)
• AN EFFICIENT METHOD FOR PREPARING GEM-DIMETHYLCYCLOPLOPANES FROM GEM-DIBROMOCYCLOPROPANES
• スピロベチバン型セスキテルペンの形式合成
• CHEMILUMINESCENT REACTIONS OF "UNMODIFIED" FLAVINS
• Riboflavin-Sensitized Photooxidation of Phenothiazines in Aqueous Solution by Laser-Irradiation
• On the Repair of Thymine and Thymidine Bromohydrins : A Possible New Model for the Damage and Repair of Nucleic Acids
• 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
• THE INHIBITION OF THE PHOTOCHEMICAL DIMERIZATION OF 1,3-DIMETHYLTHMINE BY FLAVIN AND 5-DEZAFLAVIN DERIVATIVES
• Synthetic Studies on a Picrotoxane Sesquiterpene, Coriamyrtin. I. The Grignard Reaction of 5-(2-Methyl-1,3-dioxo-2-cyclopentyl) methyl-2,5H-furanone with Isopropenylmagnesium Bromide and Stereochemistries of the Products
• Chiral Piperazines as Catalysts for the Enantioselective Addition of Diethylzinc to Aldehydes
• Synthesis of Chiral 5-Deazaflavin Derivatives and Their Use in Asymmetric Reduction of Ethyl Benzoylformate(Organic,Chemical)
• CONVENIENT SYNTHESES OF OLIGONUCLEOTIDES LINKED TO 5-DEAZAFLAVIN COENZYME MODELS AT 3'-END. INCORPORATION OF 5-DEAZAFLAVIN TO CONTROLLED PORE GLASS(CPG) SUPPORT
• THE CHEMICAL REPAIR REACTION OF THYMINE AND THYMIDINE DIOL DERIVATIVES, MODELS OF OXIDATIVELY DAMAGED NUCLEIC ACIDS, BY TRIVALENT PHOSPHORUS COMPOUNDS
• THE REDUCTIVE REPAIR OF ADENINE-1-OXIDE DERIVATIVES TO ADENINE DERIVATIVES BY γ-GLUTAMYLCYSTEINYLGLYCINE (GLUTATHIONE)
• 56 dl-Pumiliotoxin Cの立体選択的合成
• REDOX POTENTIAL OF OLIGONUCLEOTIDE LINKED TO 5-DEAZAFLAVIN COENZYME MODEL. DETECTION OF HYBRID FORMATION BY CYCLIC VOLTAMMOMETRY
• HYBRIDIZATION OF OLIGODEOXYNUCLEOTIDE WITH REXOD COENZYME MODEL; SYNTHESIS AND PROPERTIES OF THYMIDINE DECAMERS COVALENTLY LINKED TO 5-DEAZAFLAVIN
• チミジンリン酸エステルのブロムヒドリンのチミジンリン酸エステルへの変換について : チミジンヌクレオチドの酸化損傷体の修復に関するモデル反応
• Kinetics and Mechanism of Degradation and automerization of Cefotetan in Aqueous Solution
• Syntheses and Properties of 4-Deazatoxoflavins and Related Compounds
• Synthesis of 10-Arylpyrimido [4,5-b] quinoline-2,4 (3H, 10H) diones (10-Aryl-5-deazaflavins) and Their Use in Oxidations of Alcohols and Amines
• P-1 中国産イチイ科植物Taxus chinensisの新ジテルペノイド(ポスター発表の部)
• ON THE STRUCTURES OF SIX NEW DITERPENOIDS, TAXCHININS E, H, I, J, K AND TAXCHIN B
• Total Synthesis of the Alkaloid (±)-Dendrobine
• 39 dl-Dendrobineの全合成
• 光学活性リン試薬を用いる不斉レフィン化
• THREE NEW DITERPENOIDS FROM TAXUS CHINENSIS
• Synthesis of 1,3-Dimethylpyrimido [4,5-b] quinoline-2,4 (1H, 3H)-diones (1,3-Dimethyl-5-deazaalloxazines) and Related Compounds via the Intramolecular Cycloaddition of Azahexatrienes
• 夢コレクションPart2
• SYNTHESIS OF A 5-DEAZA-10-SELENAFLAVIN DERIVATIVE, A NEW TYPE OF 5-DEAZAFLAVIN REDOX COENZYME MODEL
• Asymmetric Reduction with 5-Deazaflavin. III. : Reduction of Ethyl Benzoylformate in the Presence of Chiral Ligand
• A New Synthetic Approach to 5-Deazaflavin and 5- Deaza-10-thiaflavin
• Asymmetric Reduction with 5-Deazaflavin. II. : Synthesis of Some Chiral 5-Deazaflavin Derivatives
• Simple New Method for the Synthesis of 5-Deaza-10-oxaflavin, a Potential Organic Oxidant
• ONE-POT UNSYMMETRICAL DOUBLE SUBSTITUTION OF 8,8-DIBROMOBICYCLO[5.1.0]OCTANE AND ITS STEREOCEHMISTRY
• 5-Arylidene 1,3-Dimethylbarbituric Acid Derivatives, Mild Organic Oxidants for Allylic and Benzylic Alcohols
• Stereo-Structures of Reaction Products of dl-1,3-Dimethylthymine Epoxide with Amines and L-Amino Acid Ethyl Esters(Organic,Chemical)
• Oxidation of Pyrimidine Base Derivatives with m-Chloroperbenzoic Acid
• OXIDATION OF 1,3-DIMETHYL DERIVATIVES OF PYRIMIDINE BASES WITH m-CHLOROPERBENZOIC ACID
• Synthetic Studies on a Picrotoxane Sesquiterpene, Coriamyrtin. III. Completion of the Stereocontrolled Total Synthesis of (±)-Coriamyrtin
• Synthetic Studies on a Picrotoxane Sesquiterpene, Coriamyrtin. II. An Effective Stereocontrolled Synthesis of the Picrotoxane Skeleton Except for a C_1 Unit at the C_9 Position and Functionalization of the Five-membered Ring
• 天然物合成から (有機合成の考え方--研究テ-マはどのように生まれ育ったか) -- (有機合成の発想・展開・展望--われわれの体験から)
• 41 ピクロトキサン型セスキテルペン,コリアミルチンの合成研究
• Synthesis of dl-Pumiliotoxin C Hydrochloride and Its Crystal Structure
• Total Synthesis of the Alkaloid (±)-Metaphanine
• Total Synthesis of the Alkaloid, (±)-Hasubanonine
• 24 (±)Hasubanonineの合成
• ピクロトキサン骨格を有する天然物の合成研究
• Syntheses and Properties of 3-Hydroxy-4,6-dimethylpyrrolo [3,2-d] pyrimidine-5,7 (4H, 6H)-dione (9-Hydroxy-9-deazatheophylline) Derivatives
• Constitution of Four New Hasubanan Alkaloids from Stephania japonica MIERS
• 1,3-ジメチルチミンエポキシドとアミン類との反応における溶媒効果(有機化学)
• MILD OXIDATION OF ALLYLIC AND BENZYLIC ALCOHOLS WITH 5-ARYLIDENE BARBITURIC ACID DERIVATIVES AS A MODEL OF REDOX COENZYMES
• Syntheses of Isoalloxazines. A New Synthesis of Riboflavin
• The Novel Use of Diethyl Azodicarboxylate in a New Synthesis of 7-Azapteridine-N-oxides
• 1,3,8,10,11,14-HEXAZAPENTAPHENE-2,4,7,9(14H___-, 3H___-, 8H___-, 11H___-)-TETRAONES (BENT DOUBLE-HEADED 5-DEAZAFLAVINS) WITH STRONG OXIDIZING POWER
• A CONVENIENT LEWIS ACID CATALYZED PREPARATION OF CARBAMATES FROM SECONDARY ALCOHOLS AND ISOCYANATES
• FORMATION OF 4a, 5-DIHYDRO-4a-HYDROXY-5-DEAZAFLAVINS IN THE REACTION OF 1,5-DIHYDRO-5-DEAZAFLAVINS WITH m-CHLOROPERBENZOIC ACID AND THEIR PYRIMIDINE RING CONTRACTION WITH BASE
• A Synthesis of Alloxazine 5-Oxides by the Reaction of 6-Anilinouracils with Nitric Acid and 4-Phenylurazole
• Nitrosative and Nitrative Cyclizations of 6-Benzylamino-1,3-dimethyl-4-N-phenylcytosine
• A New Synthetic Approach to 8-Chloroflavins and Their Conversion into 8-(Substituted-amino) flavins
• SYNTHESIS AND PROPERTIES OF A NEW CLASS OF PYRIDODIPYRIMIDINES, 8-ALKOXYPYRIDO [2,3-d : 6,5-d'] DIPYRIMIDINE-2,4,6 (3H, 10H, 7H)-TRIONES
• Syntheses and Properties of Some Pyrrolo[2,3-d]pyrimidine Derivatives
• Dimethylamination and Nitrosation of Pyrimidines with N-Nitrosodimethylamine
• Intermolecular Dimethylamination and Nitrosation with N-Nitrosodimethylamine
• A Novel Synthesis of 6-Deoxytheophyllines and 6-Deoxy-7-deazatheophyllines
• Thio-analogues of 6-Substituted 1,3-Dimethyl-7-azalumazine (Fervenulin) and 7-Substituted 1,3-Dimethyl-6-azalumazine (Isofervenulin)
• The Syntheses of Some Androstano [2,3-g] pteridines
• Syntheses of 1,6-Dimethylpyrimido [4,5-c] pyridazine-5,7 (1H, 6H)-diones (4-Deazatoxoflavins) and Their Use in the Autorecycling Oxidation of Alcohols and Amines
• Syntheses of Heterocycles via Intramolecular Cycloaddition of Azahexatrienes. Photochemical Cyclization of 5-Arylazo-6-dimethylaminomethyleneamino-1,3-dimethyluracils
• Syntheses of Substituted 8-Aminopurine Derivatives
• Novel Ring Expansions of Pyrrolo-pyrimidines to Pyrimido-pyrimidines
• Syntheses of 4-Methyl-s-triazolo [4,3-a] purin-9 (4H)-ones and Tetrazolo-[1,5-a] purin-9 (4H)-ones as Aza Analogs of "Y"Bases
• Synthesis and Properties of 2,3,4,8-Tetrahydro-2,4-dioxopyrido [2,3-d]-pyrimidines (5-Deazalumazines) and Their Bis-compounds
• Synthesis and Properties of 3,4-Disubstituted 1-Methylpyrimido [4,5-c] pyridazine-5,7 (1H, 6H)-diones (3,4-Disubstituted 4-Deazatoxoflavins) and 3,4-Disubstituted 4-Deazatoxoflavin Bound to Polystyrene and Their Use in Autorecycling Oxidation of Amines
• A Convenient Synthesis of Toxoflavins, Toxoflavin 4-Oxides and 1-Demethyltoxoflavins
• Cyclization Reactions of Some 5-Nitro- and 5-Nitroso-6-benzylidenehydrazinouracils
• ハスバナンアルカロイドの全合成
• Heterocycle N-Oxide Synthesis by the Nitrative Cyclization. New Syntheses of Fervenulin N-Oxide, Alloxazine N-Oxide, Isoalloxazine N-Oxide and Purine N-Oxide
• A Novel One-step Synthesis of Tricycloquinazolines
• Reaction of 5,6-Diamino-1,3-dimethyluracil with Isatoic Anhydrides
• 新しい現象との邂逅を求めて(研究の断念と新テーマの着手-研究の決断-)
• 生物劣化を受けた木材の曲げおよび圧縮強度特性とその劣化評価

もっと見る 閉じる

スポンサーリンク