Formic Acid Reduction. XVL. Mechanism of the N-Methylation of p-Phenylenediamine Derivatives with Formates
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概要
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Mechanistic investigation on the previously reported N-methylation of formanilides effected by the constant-boiling liquid of the formates composed of formic acid and trialkylamine has been made by introducing isotopic tracer method into the representative reaction of p-phenylenediamine derivatives. In accord with the isotopic tracer results a mechanism of this formate reaction has been proposed. It has been revealed that the formate reagents affect the conversion of N-formyul, which suffers interchange in the formate medium, into N-methyl acting as reducing agent.
- 社団法人日本薬学会の論文
- 1972-12-25
著者
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鈴木 邦夫
School Of Pharmaceutical Sciences University Of Shizuoka
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鈴木 邦夫
Shizuoka College of Pharmacy
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関屋 実
Shizuoka College of Pharmacy
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鈴木 次郎
Shizuoka College of Pharmacy
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高山 修一
Shizuoka College of Pharmacy
関連論文
- Prostanoids and Related Compounds. IV. Total Synthesis of Clavulones
- Cyclization of α- and β-Alkylthio-Substituted Amines Possessing Positively Charged Carbon at the Nitrogen. A New Synthetic Method for Thiazolidines, Thiomorpholines and Dihydro-1,4-benzothiazines
- Reactions of 2,2-Dichlorovinyl and 2,2-Dichlorovinylidene Sulfides with Butyllithium
- Thermal Rearrangements of Allyl 2,2-Dichloro-, 1,2-Dichloro- and 1,2,2-Trichloro-substituted Vinyl Sulfides
- Novel Rearrangements of α-N-Alkylamido-substituted Sulfides and Sulfones
- Syntheses and Reactions of Phenylthio-and Propylthioacetylenic Compounds
- Enantioface-Differentiating Epoxidation of Alkylidenemalononitriles with Molecular Oxygen, catalyzed by Chiral Tertiary Amines
- Formic Acid Reduction. XXVIII. Kinetic Studies on the Formic Acid Reduction of 1,1'-Benzylidenedipiperidine
- A New Insertion Reaction of Diazoalkanes with Dialkylaminomethyl Esters of Dialkyldithiocarbamic Acid and of Ethylxanthic Acid
- Chlorinolyses of Alkyl (or Aryl) Phthalimidomethyl Sulfoxides with Sulfuryl Chloride, Chlorine and Thionyl Chloride
- Nucleophilic Substitution of Alkyl (or Aryl) Imidomethyl Sulfones. A New Convenient Synthesis of Alkane (or Arene) sulfinates
- Decarboxylation Reaction. VIII. Reaction of Electron-deficient Carbon-Carbon Double Bonds with Trichloroacetic Acid. A Unique 1,1-Dichlorocyclopropane Formation through β-Trichloromethylation
- Formic Acid Reduction. XXVI. α, β-Reduction of Conjugated Nitriles with Formic Acid
- Decarboxylation Reactions. V. Reaction of N-Benzylideneanilines with Propiolic Acid
- Formic Acid Reduction. XXIV. Path of the Reductive Fission of the Centered β-Carbon Bond of Alkylidenebisketones
- Formic Acid Reduction. XXIII. Kinetic Studies on the Formic Acid Reduction of Carbon-Carbon Double Bond Adjacent to Carbonyl
- Formic Acid Reduction. XXII. Reaction of α, N-Diphenylnitrone with Formic Acid
- Formic Acid Reduction. XXI. Reductive Cleavage Reaction of p-Dimethylamino-substituted Triphenylmethanes induced by Formate
- Formic Acid Reduction. XX. Reduction of 2-Benzylidene-1,3-indandiones
- Formic Acid Reduction. XIX. Formic Acid Reduction of 4-Dialkylaminosubstituted Nitro-, Nitroso-, Azoxy-and Azobenzenes
- Formic Acid Reduction. XXVIII. Kinetic Studies on the Formic Acid Reduction of 1,1'-Benzylidenedipiperidine
- Preparation of N-Alkylthiomethyl Derivatives of Hydroxylamines
- N-[(N-Nitrosoalkylamino) methyl] carbamates as New and Convenient Diazoalkane-generating Agents
- Thermal and Photochemical Behaviors of N-[(N-Nitrosobenzylamino)-methyl] benzamide in Acidic Media
- Preparations of N-Alkylthiomethyl and N-Amidomethyl Derivatives of Amino Acids
- Chemical Behaviors of 1,1'-Diacetyl-1,1', 4,4'-tetrahydro-4,4'-bipyridine toward Organic Hydrogen Acceptors
- A New Convenient Synthesis of Diazoalkanes from N-[(N-Nitrosoalkylamino) methyl] benzamides
- Decarboxylation Reactions. III. Reaction of N, N'- and N, O-Linked Methylene Compounds with Carboxylic Acids
- Reaction of N-(Alkoxymethyl) dialkylamines and N, N'-Methylene-bisdialkylamines with Isocyanides
- Reductive Cleavage Reaction of N, N'-, N, O- and N, S-Linked Alkylidene Compounds by Sodium Borohydride
- On Behaviors of N-(Dialkylaminomethyl) imides and-amides toward Nucleophiles
- Reaction of N-(Dialkylaminomethyl) amides and N-(α-Dialkylaminobenzyl) amides with Sulfides and Cyanide
- Formic Acid Reduction. XV. Reaction of N-Methyl and N-Formyl Derivatives of p-Phenylenediamine with Formates. N-Methylation of Formanilides
- Formic Acid Reduction. XIII. Formate Reaction of the Compounds possessing the Carbon Bound to Both Oxygen and Nitrogen
- Catalytic Hydrogenation of Tetrahydro-4H-1,3-oxazin-4-ones and 4-Oxazolidinones
- Catalytic Hydrogenolyses of Benzylidene Compounds Bound to Two Oxygens, Two Nitrogens and Both Oxygen and Nitrogen
- Catalytic Hydrogenation of Hydroamide in the Presence of Ammonia and of Butylamine
- Formic Acid Reduction. XXVIII. Kinetic Studies on the Formic Acid Reduction of 1,1'-Benzylidenedipiperidine
- Formic Acid Reduction. XXVIII. Kinetic Studies on the Formic Acid Reduction of 1,1'-Benzylidenedipiperidine
- Formic Acid Reduction. XXVIII. Kinetic Studies on the Formic Acid Reduction of 1,1'-Benzylidenedipiperidine
- Formic Acid Reduction. XXVIII. Kinetic Studies on the Formic Acid Reduction of 1,1'-Benzylidenedipiperidine
- Formic Acid Reduction. XXVIII. Kinetic Studies on the Formic Acid Reduction of 1,1'-Benzylidenedipiperidine
- Formic Acid Reduction. XXVIII. Kinetic Studies on the Formic Acid Reduction of 1,1'-Benzylidenedipiperidine
- Trifluoromethanesulfonic Acid-Promoted Reaction of Hexahydro-1,3,5-triazines.Introduction of a Secondary Aminomethyl Grouping into Carboxylates at the α-Position through Ketene Silyl Acetals
- Pyrrolidine-Forming 1,3-Dipolar Cycloaddition of N-(Phenylthiomethyl)-α-amino Acid Esters
- A New Method for the Introduction of Arylthio Groups at the α-Position of Alicyclic Amines
- Primary Aminomethylation at the α-Position of Carboxylic Acids and Esters. Trimethylsilyl Triflate-Catalyzed Reaction of Ketene Silyl Acetals with N, N-Bis (trimethylsilyl) methoxymethylamine
- 1,3-DIPOLAR CYCLOADDITION LEADING TO N-ALKYLPYRROLIDINES
- 1,3-Dipolar Cycloaddition Leading to N-Acylated Pyrrolidines and 2,5-Dihydropyrroles
- Decarboxylation Reaction. X. Introduction of a Carbon Unit at the α-Position of Amines by Reaction of Hexahydro-1,3,5-triazines with Carboxylic Acids
- Synthesis of Deoxyobtusilactone A
- Reactions of 2,2,2-Trichloroethylamines with Grignard Reagents and Alkyllithiums
- A New Route to 4-Unsubstituted β-Lactams through Ureidomethylation of Ketene Silyl Acetals
- New Syntheses of α-N-Alkylacetamidomethylated Carbonyl Compounds
- N-Alkylamidomethylation at Electron-rich Carbons in the 1,3,5-Trialkylhexahydro-1,3,5-triazine-Acetyl Chloride System
- One Step Syntheses of Adenine, Xanthine and Guanine from Phenylazomalonic Acid Derivatives
- One Step Syntheses of Hypoxanthines from 2-Cyano-2-phenylazoacetamides
- Facile Syntheses of Xanthines from Uric Acids
- Monobromination of Cyanoacetamides and Amidinoacetamide with Molecular Bromine
- Formic Acid Reduction. XVIII. Formic Acid Reaction of p-(Dialkylamino) azobenzenes
- Formic Acid Reduction. XVL. Mechanism of the N-Methylation of p-Phenylenediamine Derivatives with Formates
- Reaction of Amide Homologs. XXVI. On the Products obtained from the Reaction of N-Alkylphenylacetamides with Phosphoryl Chloride
- Facile Syntheses of Hypoxanthine and Adenine
- Azole Series. III. Reactions of 2-Acylamino-2-cyanoacetamides leading to 5-Aminooxazole-4-carboxamides and to Oxazolo [5,4-d] pyrimidines
- Azole Series. II. Reactions of 2-Acylamino-2-cyanoacetamides leading to 5-Acylaminooxazole-4-carboxamides and to Oxazolo [5,4-d] pyrimidines
- Formic Acid Reduction. V. Barbituric Acid Derivatives. Reaction of 5-(3-Indolylmethylene) barbituric Acid with the Formate
- Formic Acid Reduction. IV. Barbituric Acid Derivatives. Reduction of 5-Arylmethylenebarbituric Acids and Some Analogous Barbituric Acid Derivatives
- Reaction of Amide Homologs. XIX. Thermal Reactions of Azomethines with Formates and Formamide
- Reaction of Amide Homologs. XVIII. Catalytic Hydrogenation of N-Arylmethylene-1-acylamino-1-arylmethylamines and Hydroamides in the Presence of Formamide and Related Studies
- Reaction of N-(Butoxymethyl) dialkylamines and N, N'-Methylenebis-(dialkylamine)s with N-(1-Cyclohexen-1-yl) dialkylamines
- Reaction of Amide Homologs. VI. Aminomethylation of Salicylic Acid with N, N'-Methylenebisacetamide.
- Catalytic Hydrogenation of Azomethines in the Presence of Ammonia or Amines.
- Reaction of Amide Homologs. V. Acetamidomethylation of Phenol and Anisole with N, N'-Methylenediacetamide.
- A Novel 2,3-Pyrrolidinedione Ring Closure of 1,1,1,5,5,5-Hexachloro-4-dimethylamino-3,3-dimethyl-2-pentanone
- Reaction of N, N-Dialkylaminomethyl Arenesulfonates with Diazoalkanes
- Decarboxylation Reactions. IX. Reaction of Enamines with Trichloroacetic Anhydride
- Decarboxylation Reactions. VI. Reaction of α-Arylmethyleneamino-substituted Derivatives of Pyridine, Quinoline, and Isoquinoline with Trichloroacetic Anhydride
- Reactions of α-Alkyl- and α-Aryl-substituted N-Benzylideneamines with Trihaloacetylating Agents
- Reaction of Schiff Bases with Trichloroacetyl Chloride in the Presence of Triphenylphosphine
- Decarboxylation Reactions. IV. Reaction of Schiff Bases with Trichloroacetic Anhydride
- Reaction of 1-Pyrrolidino-1-cyclohexene with Imidoyl Chlorides and a Route to Producing Phenanthridines
- Intramolecular Aldol Condensations of the Reaction Products formed from 2,4-Pentanedione and Aldehydes
- Vapor-Liquid Equilibrium for Formic Acid-Triethylamine System Examined by the Use of a Modified Still. Formic Acid-Trialkylamine Azeotropes
- Reduction of β-Chlorovinylaldehydes with Zinc Powder
- C-Alkylation of α-Amidoketones
- Reaction of Amide Homologs. X. Mechanism of the Formation of N-Arylmethylene-1-acylamino-1-arylmethylamine.
- Reaction of Amide Homologs. IX. Catalytic Hydrogenation of Azomethines in the Presence of Amide and its Mechanism.
- Syntheses of Bradykinin Analogs Containing Sarcosine Residues and Their Biological Activities
- Reaction of Amide Homologs. XVI. α-Acetamidoalkylation of β-Naphthol and 2,6-Xylenol
- Synthesis of 1-Glutamic Acid Kallidin
- Reaction of Amide Homologs. XI. Benzamidomethylation of Aromatic Compounds.
- Reaction of Amide Homologs. III. α-Acylamidoalkylation of 2,4-Xylenol with Bisamides.
- A New α-Acylaminoalkylation of Aromatic Compounds
- N-[(N-Nitrosoarylamino) methyl] succinimide as a New Agent Generating Aromatic Diazotate
- Reaction of Amide Homologs. XII. Reaction of N-Arylmethylene-1-acylamino-1-arylmethylamine with Active Methylene Compound.
- Decarboxylation Reactions. I. Reaction of Enamines with Carboxylic Acids
- Formic Acid Reduction. XII. Reductive Fission of Bridged Carbon-Carbon Bond of α, α'-Benzylidene- and α, α'-Methylene-bisketones
- Formic Acid Reduction. X. Reductive Fission of Bridged Carbon-Carbon Bond of Bisdimedone Derivatives
- Formic Acid Reduction. IX. Reactions of 5,5-Dimethyl-1,3-cyclohexanedione with TEAF and Their Reaction Routes
- Formic Acid Reduction. VII. Reduction of Carbon-Carbon Double Bonds adjacent to Carbonyls