Reduction with Formic Acid. I. Reduction of N-Acylaminomethyl and N-Sulfonamidomethyl Compound.
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概要
- 論文の詳細を見る
A number of N-acylaminomethyl and N-sulfonamidomethyl compounds were subjected to formic acid reduction using trimethylammonium formate as a reducing agent. The reduction was found to lead to a fission of the carbon bond connecting to the amide nitrogen. Ease of the reduction increased with lowering the electron density of the amide nitrogen. The compounds attached to aliphatic amine underwent the reduction almost quantitatively and, on the other hand, the aromatic amine homologs were less reactive. A possible mechanism for the reduction was proposed.
- 公益社団法人日本薬学会の論文
- 1964-06-25
著者
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伊藤 敬一
Hokkaido College Of Pharmacy
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関屋 実
Shizuoka College of Pharmacy
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伊藤 敬一
Shizuoka College of Pharmacy
関連論文
- 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
- 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
- N-COUMARINYL-L-PROLINE, A NOVEL CHIRAL DERIVATIZING AGENT FOR ^1H NMR DETERMINATION OF ENANTIOMERIC PURITIES OF ALCOHOLS AND AMINES
- NEW REDUCTION OF SULFOXIDES AND SULFILIMINES TO SULFIDES WITH ZINC/1,4-DIBROMOBUTANE, A PROPOSAL FOR A RADICAL-FORMING ELECTRON TRANSFER PROCESS(Communications to the Editor)
- Preparation of N-Alkylthiomethyl Derivatives of Hydroxylamines
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- Thermal and Photochemical Behaviors of N-[(N-Nitrosobenzylamino)-methyl] benzamide in Acidic Media
- Preparations of N-Alkylthiomethyl and N-Amidomethyl Derivatives of Amino Acids
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- 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
- バルビツール酸およびその誘導体のジアゾメタンによるメチル化
- 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
- Studies on Stable Diazoalkanes as Potential Fluorogenic Reagents. III. : 4-Diazomethyl-2(1H)-quinolinones(Organic,Chemical)
- Studies on Stable Diazoalkanes as Potential Fluorogenic Reagents. II. : Ring-Fused 4-Diazomethylcoumarins
- On the Spectral Properties of Some Fused 4-Methylcoumarins
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- 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
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- 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
- Paper Chromatographic Detection of Nitrogen Mustard
- 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.
- Reaction of Amide Homologs. XII. Reaction of N-Arylmethylene-1-acylamino-1-arylmethylamine with Active Methylene Compound.
- Reaction of Amide Homologs. XXI. N-Monomethylation of Aromatic Primary Amines. A Method through the Formation of N-Succinimidomethyl Compound.
- ギ酸による還元反応(第2報) : 含窒素芳香環化合物の還元
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- Reaction of Amide Homologs. XIII. Catalytic Hydrogenolysis of N-Acylaminomethyl and N-Arylsulfonamidomethyl Compounds
- Reduction with Formic Acid. I. Reduction of N-Acylaminomethyl and N-Sulfonamidomethyl Compound.
- Reaction of Amide Homologs. VIII. Catalytic Hydrogenolysis of O- or N-Acylaminomethyl and N-α-Acylaminobenzyl Compounds.
- Reaction of Amide Homologs. VII. Formation of N- (α-Dialkylaminobenzyl) acetamides from N-Benzylidene-α-acetamidobenzylamine.