Reaction of N-Aminopyridinium Derivatives. II. The Reactions of 1-(N-Acylalkylamino) pyridinium Salt Derivatives with Cyanide Ion. : A New Synthesis of Primary Amines.
スポンサーリンク
概要
- 論文の詳細を見る
1-(N-Monosubstituted amido) pyridinium compounds derived from novel quaternary salts of pyridine, N-aminopyridinium compounds, were quite reactive to nucleophilic agents at 2- and 4-positions of their pyridine rings, especially at 4-position. The 1-(N-monosubstituted amido) pyridinium salts were reacted with cyanide ion to give N-monosubstituted amides and cyanopyridines, (predominantly 4-cyanopyridine), both in good yields. The reaction may involve dihydro-type intermediates and one intermediate 1-(N-methylacetamino)-4-cyano-1,4-dihydropyridine could be obtained stably. By utilizing this reaction, it would be possible to introduce a cyano group at 4-position of various pyridine derivatives and to obtain various primary amines.
- 公益社団法人日本薬学会の論文
- 1963-06-25
著者
-
広部 雅昭
Faculty of Pharmaceutical Sciences, University of Tokyo
-
岡本 敏彦
Faculty of Pharmaceutical Sciences, University of Tokyo
-
大沢 昭緒
東京大学薬学部
-
岡本 敏彦
Faculty Of Pharmaceutical Sciences University Of Tokyo
-
広部 雅昭
Faculty Of Pharmaceutical Sciences University Of Tokyo
-
大沢 昭緒
Faculty of Pharmaceutical Sciences, University of Tokyo
-
水島 千恵子
Faculty of Pharmaceutical Sciences, University of Tokyo
-
水島 千恵子
Faculty Of Pharmaceutical Sciences University Of Tokyo
関連論文
- BACTERIOSTATIC EFFECT OF 4,7-DICYANOBENZOFURAZAN DUE TO INACTIVATION OF 2,3-DIHYDROXYISOVALERATE DEHYDRATASE
- FORMATION OF SUPEROXIDE BY BENZOFURAZANS IN ESCHERICHIA COLI UNDER AEROBIC INCUBATION
- Toxicities of Dicyanobenzofurazans with Formation of Superoxide in Escherichia coli
- Degradation of 1,3-Diaryl-1-nitrosoureas in Aqueous Solutions and in Organic Solvents(Organic,Chemical)
- Studies on the Oxidation of 5H-N-Substituted Dibenz[b, f]azepines. III. : Oxidative Metabolism by Rat Liver Microsomes
- Studies on the Oxidation of N-Substituted-dibenz [b, f] azepines. II. Syntheses and Reactions of 5H-Dibenz [b, f] azepine 10,11-Oxides
- OXIDATION OF TERTIARY AMINES AND SULFIDES BY AN IRON (III) PORPHYRIN-O_2-Na_2S_2O_4 SYSTEM AS A MODEL OF CYTOCHROME P-450
- Oxidative Dealkylation of Tertiary Amines by Iron (III) Porphyrin-Iodosoxylene System as a Model of Cytochrome P-450
- Studies on the Oxidation of N-Substituted-dibenz [b, f] azepines I. Oxidation with m-Chloroperbenzoic Acid
- Synthesis and Analgesic Activity of Morphine-7,8-oxide and Heroin-7,8-oxide
- Codeine-7,8-oxide (4,5α-Epoxy-7β, 8β-epoxy-3-methoxy-17-methylmorphinan-6α-ol) : Identification as a Metabolite of Codeine
- Stereospecific Synthesis of Codeine 7,8-Oxide and Codeinone 7,8-Oxide
- Reactions of K-Region Oxides of Carcinogenic and Noncarcinogenic Aromatic Hydrocarbons. Comparative Studies on Reactions with Nucleophiles and Acid-catalyzed Reactions
- INTER-INDIVIDUAL DIFFERENCES OF (+)-4-[4-(4-METHYLPHENYL)PHENYLMETHOXY-1-PIPERIDINYL]BUTYRIC ACID ((+)-MPPB) DISPOSITION IN RATS
- 18 サイトカイニン作用をもつ二,三のウレア化合物のイネ苗条テストで示す伸長促進作用
- 4-Pyridylureas are surprisingly Potent Cytokinins. The Structure-Activity Relationship
- Isolation and Structure Studies of Mutagenic Principles in Amino Acid Pyrolysates
- Synthesis of a Mutagenic Principle isolated from Tryptophan Pyrolysate
- ISOLATION AND STRUCTURAL DETERMINATION OF MUTAGENIC SUBSTANCES IN COAL TAR
- THE STRUCTURE AND ABSOLUTE CONFIGURATION OF SADOSINE
- THE STRUCTURE OF IGNAVINE
- A Potent Mutagen isolated from a Pyrolysate of L-Ornithine
- A Potent Mutagen isolated from a Pyrolysate of L-Ornithine
- Ultramicro Analysis of Benzo [α] pyrene in Food
- Synthesis and Mutagenicity of 10-Azabenzo [α] pyrene-4,5-oxide and Other Pentacyclic Aza-arene Oxides
- NEW METHOD OF DETECTING NITRIC OXIDE PRODUCTION
- A Novel Method for Angular Functionalized Methylation via Ring Opening of Bromocyclopropane
- 35 MorphinanおよびB/C trans-morphinanの合成
- 不活性C-H結合に対する新攻撃法とそのエンメインよりジベレリンA_合成への応用 : ダイテルペノイドの化学的研究(第1報)
- A Novel Method for Attacking Non-activated C-H Bond and Its Application to the Synthesis of Gibberellin-A_ from Enmein
- Plant Growth Regulators in the Pea Plant (Pisum sativum L.)
- Quantitative Estimation of Auxins and Antiauxin in Etiolated Seedlings of Phaseolus Bean by Gas Chromatography and Colorimetry. I
- Studies on Plant-Growth Regulators. IV. Structure of Growth Retardants and Syntheses of Related Compounds
- Reaction of 4α, 10α-Bromomethano-1,1-dimethyl-9-oxo-1,2,3,4-tetrahydrophenanthrene with Nucleophiles
- Lycoricidinol and Lycoricidine, New Plant-growth Regulators in the Bulbs of Lycoris radiata HERB.
- Synthesis of 4α-Formyl-1,2,3,4,4α, 10-hexahydrophenanthrene. A New Method for Angular Formylation
- Structure Elucidation of a New Aconite Alkaloid, 15-α-Hydroxyneoline
- Structural and Biological Links between Urea- and Purine-cytokinins
- Cytokinin Activity of Pyrimidine Derivatives
- Studies on the Constituents of Isodon trichocarpus KUDO. II. The Structures of Enmenin, Enmelol, and Ememodin
- Studies on the Constituents of Isodon trichocarpus KUDO. I. Isolation of the Constituents and the Structures of Isodonol, Enmedol, and Enmenol
- Clusters [Fe_4S_4(SR)_4]^ as Novel Catalysts in Organic Reductions
- Reaction Mechanism in Aromatic Heterocyclic Compounds. X. Kinetics of the Reaction of Carcinogenic 4-Nitroquinoline 1-Oxide and Its Derivatives with Sodium Ethoxide
- The Structure of Lucidusculine and the Absolute Configuration of Songorine
- Steric and Electronic Effects of Methyl Substitutents at the 2- and 6-Positions on N-Benzyl-1.4-dihydronicotinamide(Organic,Chemical)
- Novel Rearrangement of Pyrazole N-Imines with Acetic Anhydride
- Syntheses of Novel Antimicrobial Compounds : Pyrazolo [5,1-b] thiazole, Imidazo [1,2-b] pyrazole, and Thiazolo [3,2-b] dihydro-1,2-diazepine
- THREE NEW ALKALOIDS, RYOSENAMINE, RYOSENAMINOL, AND IBUKINAMINE FROM ACONITUM IBUKIENSE NAKAI
- pH Lowering in Liposomal Dispersiond Induced by Phospholipid Peroxidation
- Alkyl Chain Length Dependency in Hydrolysis of Liposomal Phosphatidylcholine by Dialkylphosphate
- Toxicity of Singlet Oxygen Generated Thermolytically in Escherichia coli
- Characteristic Coloration in Formation of N-1-Pyridinio Amidate and Enhancing Effect of Benzaldehydes
- A Novel Metabolite of 3,4-Methylenedioxyamphetamine (MDA) : Formation of 3-Methyl-6,7-methylenedioxy-1,2,3,4-tetrahydroisoquinoline and Its Pharmacological Effect
- Oxygen Activation by Iron(III)-Porphyrin/NaBH_4/Me_4N・OH System as Cytochrome P-450 Model. Oxygenation of Olefin, N-Dealkylation of Tertiary Amine, Oxidation of Sulfide, and Oxidative Cleavage of Ether Bond
- COMPARISON OF THE REACTIVITIES OF [Fe_4S_4(SPh)_4]^ AND [Fe_2S_2(SPh)_4]^
- REVERSIBLE ELECTROCHEMICAL REDUCTION OF 1,6,6a-TRITHIA-3,4-DIAZA-PENTALENES TO THEIR ANION RADICALS WITH THE PRODUCTION OF SUPEROXIDE
- COOXIDATION OF ENONES DURING REACTION OF SUPEROXIDE WITH ACIDIC AROMATIC AMINES
- INCREASING 5-LIPOXYGENASE INHIBITORY ACTIVITIES BY OXIDATIVE CONVERSION OF O-METHOXYPHENOLS TO CATECHOLS USING A Cu^ - ASCORBIC ACID - O_2 SYSTEM
- The Structure of Nobilonine. The Second Alkaloid from Dendrobium nobile
- The Structure of Dendrobine
- Rearrangement of 4-Acetoxy-2H-1,4-benzoxazin-3 (4H)-one
- A Fungal Metabolite, Novel Isocyano Epoxide
- The Crystal Structure of the Bromoacetylated Dimer-A synthesized by the Reaction of Acridine with Hydroxylamine-O-sulfonic Acid
- Uber die Shimoburobase-II und die Takaobase-I
- THE CONVERSION OF PSEUDOKOBUSINE TO KOBUSINE
- THE STRUCTURE OF THE NEW DITERPENE ALKALOID NOMININE AND THE ABSOLUTE CONFIGURATION OF KOBUSINE
- THE STRUCTURE OF A NEW DITERPENE ALKALOID : SANYONAMINE
- THE STRUCTURE OF HYPOGNAVINE
- THE PARTIAL SYNTHESIS OF ISODELPHININE
- Studies on the Chlorinated α-Santonins. I
- Reaction of Phenanthrene-9,10-oxide with Tetracyanoethylene
- The Structure of Isohypognavine
- Structural Correlation of Kobusine to Pseudokobusine
- Reaction Mechanism in Aromatic Heterocyclic Compounds. III. Kinetics of the Reaction of 4-Haloquinoline 1-Oxides and Related Compounds with Piperidine.
- Studies on Photochemical Reaction of Air Pollutants. X. Identification of Nitrophenols in Suspended Particulates
- Studies on Photochemical Reactions of Air Pollutants. IX. Formation of o-Nitrophenol and p-Nitrophenol by Reaction of Benzene Oxide with NO_2 in Air
- Studies on Photochemical Reactions of Air Pollutants. VIII. Photochemical Epoxidation of Olefins with NO_2 in a Solid-Gas Phase System
- Chemical Structure of QA_, One of the Covalently Bound Adducts of Carcinogenic 4-Nitroquinoline 1-Oxide with Nucleic Acid Bases of Cellular Nucleic Acids
- Studies on Chemical Alterations of Nucleic Acids and Their Components. VIII. Alkaline Rearrangement of 1-Aminoadenosine to 5-Amino-1-β-D-ribofuranosyl-4-(1,2,4-triazol-3-yl) imidazole
- Application of NMR to Stereochemistry. (I). The Spatial Interaction Effect of the Hydroxyl Group to Methyl Resonance.(53)
- Synthesis of Non-K-region Dihydrodiols and Epoxides of Carcinogenic Dibenz [c, h] acridine
- Identification of an Ultimate Mutagen of 10-Azabenzo [α] pyrene : Microsomal Oxidation of 10-Azabenzo [α] pyrene to 10-Azabenzo [α] pyrene-4,5-oxide
- Aconite Aldaloids. XXIV. The Structure of Ignavine. (4).
- The Aconite Alkaloids. XXIII. The Structure of Ignavine. (3).
- Reaction of N-Aminopyridinium Derivatives. V. Syntheses of 1-(N-Methylacetamido) alkylpyridinium Salts and Their Reaction with Cyanide Ion.
- Reaction of N-Aminopyridinium Derivatives. II. The Reactions of 1-(N-Acylalkylamino) pyridinium Salt Derivatives with Cyanide Ion. : A New Synthesis of Primary Amines.
- Comparison of Singlet Oxygen Production Efficiency of C_ with Other Photosensitizers, Based on 1268nm Emission
- Application of Chemical P-450 Model Systems to Study Drug Metabolism. III. : Metabolism of 3-Isobutyryl-2-isopropylpyrazolo[1,5-α]pyridine
- FACILE PREPARATION OF UNSTABLE METABOLIC INTERMEDIATES : EPOXIDE(S) OF PYRAZOLO[1,5-a]PYRIDINE DERIVATIVES BY THE CYTOCHROME P-450 CHEMICAL MODEL
- OXYGEN ACTIVATION AND OLEFIN OXYGENATION BY IRON (III) PORPHYRIN AS A MODEL OF CYTOCHROME P-450
- Oxidation of Sulfides and Epoxidation of Olefins Caused by the Reaction of Pd-Peroxo or Co-Superoxo Complex with Carboxylic Acid Derivatives
- 3-Alkoxycarbonyl-2-oxazolones and Their Homopolymers as Highly Preservable Amino-Protecting Reagents. tert-Butoxycarbonylation and Benzyloxycarbonylation of Amino Groups
- Thermal Equilibrations of 1,11-Dioxa [11] paracyclophane Derivatives in Cholesteric Liquid Crystals
- Facile Desulfurization of Thiocarbonyl Groups to Carbonyls by Superoxide. A Model of Metabolic Reactions
- Disulfide Cleavage and Insulin Denaturation by Active Oxygen in the Copper(II)/Ascorbic Acid System
- Reaction of N-Aminopyridinium Derivatives. IV. Syntheses of N-Aminoquinolinium Salts and Their Reaction with Cyanide Ion
- o_2-cu^-ASCORBIC ACID : A NOVEL OXIDATION SYSTEM FOR THE HIGHLY SELECTIVE O-CEALKYLATION OF 2-ALKOXYPHENOLS
- Epoxidation of Olefins by Superoxide in the Presence of Acyl Halide
- Effects of Epoxidation on the Actions of Normorphine, Norcodeine, N-Allylnormorphine (Nalorphine) and N-Allylnorcodeine on the Electrically Stimulated Guinea Pig Ileum
- Facile Synthesis of 3-Methylbenzene Oxide and 1-Methylbenzene Oxide, and ^1H-NMR Data for Diels-Alder Adducts of Three Methylbenzene Oxides with 4-Phenyl-1,2,4-triazoline-3,5-dione