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

スポンサーリンク

概要

• 論文の詳細を見る

• 3,4-Disubstituted 1-methylpyrimido [4,5-c] pyridazine-5,7 (1H, 6H)-diones (3,4-disubstituted 4-deazatoxoflavins) and their analogues (II) were synthesized by the condensation of 6-(1-methylhydrazino) uracil derivatives (I) and appropriate α-diketones. Reduction of II with sodium dithionite in aqueous ammonia gave the corresponding 3,4-disubstituted 4,8-dihydro-4-deazatoxoflavins (III). Ethylation of IIf with ethyl iodide yielded the corresponding 3,4-disubstituted 6-ethyl-4-deazatoxoflavin (VI). Treatment of IIh with chloromethylated polystyrene and potassium carbonate in dimethylformamide (DMF) gave the corresponding 3,4-disubstituted 4-deazatoxoflavin resin (VII). The reaction of II with m-chloroperbenzoic acid in chloroform gave the corresponding 3,4-disubstituted 4,4a-epoxy-4-deazatoxoflavins (IV). Treatment of IV with 10% aqueous sodium carbonate resulted in the formation of oxazolonopyridazine derivatives (V). The oxidizing abilities of II, VI, and VII toward amines were examined to explore the usefulness of these compounds as oxidation-reduction catalysis. These compounds (II, VI, and VII) oxidized long-chain alkylamines such as n-octylamine, n-dodecylamine besides benzylamine and cyclohexylamine to yield the corresponding carbonyl compounds (via imines) catalytically with a remarkably high turnover number.

• 公益社団法人日本薬学会の論文
• 1984-03-25

著者

• 米田 文郎

  Faculty Of Pharmaceutical Sciences Kyoto University

• 永松 朝文

  Faculty Of Pharmaceutical Sciences Okayama University

• 佐久間 義治

  Faculty of Pharmaceutical Sciences, Kumamoto University

• 橋口 裕子

  Faculty of Pharmaceutical Sciences, Kumamoto University

• 橋口 裕子

  Faculty Of Pharmaceutical Sciences Kumamoto University

• 佐久間 義治

  Faculty Of Pharmaceutical Sciences Kumamoto University

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
• 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)
• 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
• Reactivity of Isocoumarins. I. Effect of a Neighboring Hydroxyl Group on the Reduction of the Lactone Carbonyl Group
• 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
• Syntheses and Properties of 3-Hydroxy-4,6-dimethylpyrrolo [3,2-d] pyrimidine-5,7 (4H, 6H)-dione (9-Hydroxy-9-deazatheophylline) Derivatives
• 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)
• A NEW NITRATION PRODUCT, 3-NITRO-4-ACETAMIDOPHENOL, OBTAINED FROM ACETAMINOPHEN WITH NITROUS ACID
• 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
• New Syntheses of Alloxazine 5-Oxides and Fervenulin 4-Oxides by the Nitrative Cyclization
• 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
• Synthesis and Properties of 1,3-Dimethyl-6-azalumazines (Isofervenulins)
• 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
• 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-)

もっと見る 閉じる

スポンサーリンク