Equilibrium Studies of 5-Substituted 4-Hydroxy-2-methylpyrimidines. V. Lactim-Lactam Tautomerism in Ethereal Solvents
スポンサーリンク
概要
- 論文の詳細を見る
Lactim-lactam tautomerism of 5-carbethoxy-4-hydroxy-2-methylpyrimidine (1) was examined in the ethereal solvents (ethyl ether, n-propyl ether, isopropyl ether, n-butyl ether and p-dioxane). Compound 1 existed as a mixture of the lactim form (4-pyrimidinol, I) and the lactam form (4(3H)-pyrimidone, IIb) in the ethers, except p-dioxane. In p-dioxane, 1 existed mainly in the lactam form, IIb. A method was deviced to estimate spectrophotometrically the tautomeric equilibrium constant (K_t ; K_t=[IIb]/[I]). The lactim form decreased with increasing the polarity of the solvent, 9.0% (IIb, 91.0%) in isopropyl ether ; 10.5% (IIb, 89.5%) in n-propyl ether and 14.7% (IIb, 85.3%) in n-butyl ether. The lactim-lactam tautomerism of 2-hydroxynicotinic acid esters (ester R ; CH_3 (5), n-C_8H_<17> (5')) and 4-hydroxynicotinic acid esters (ester R ; CH_3 (8), n-C_8H_<17> (8')) was also examined because of a structural resemblance to 1. Compound 5 existed as a mixture of the lactim form (2-pyridinol) and the lactam form (2(1H)-pyridone) in the ethers. The lactim form of 5 existed in amounts, 10-70% (lactam form ; 30-90%). Compound 8 existed mainly in the lactim form (4-pyridinol) in all the ethers. The presence of the lactim form may be resulted form an intramolecular hydrogen bonding of these compounds.
- 社団法人日本薬学会の論文
- 1978-05-25
著者
-
松本 久美子
Faculty Of Pharmaceutical Sciences Kumamoto University
-
北川 隆康
Shionogi Research Laboratories, Shionogi & Co., Ltd.,
-
北川 隆康
Shionogi Research Laboratories Shionogi & Co. Ltd.
-
松本 久美子
Shionogi Research Laboratory, Shionogi and Co., Ltd.
-
平井 瑛三
Shionogi Research Laboratory, Shionogi and Co., Ltd.
-
北川 隆康
塩野義製薬(株)研究所
-
平井 瑛三
Shionogi Research Laboratories Shionogi & Co. Ltd.
関連論文
- Application of Fluorescent Triazoles of Analytical Chemistry. IV. : Development of a New Fluorescent Probe for Basic Drug-α_1-Acid Glycoprotein Binding Measurement
- Studies on the Interaction of Pyridone Carboxylic Acids with Metals
- A New Sapogenol and Other Constituents in Abri Semen, the Seeds of Abrus precatorius L. I
- In Vitro Dissolution Profile and in Vivo Absorption Study of Sustained-Release Tablets Containing Chlorpheniramine Maleate with Water-Insoluble Glucan
- Sustained-Release Dosage Forms Containing Chlorpheniramine Maleate with Water-Insoluble Glucan
- Equilibrium Studies of 5-Substituted 4-Hydroxy-2-methylpyrimidines. VI. Ethereal Solvents Effect on the Lactim-Lactam Tautomerism
- Equilibrium Studies of 5-Substituted 4-Hydroxy-2-methylpyrimidines. V. Lactim-Lactam Tautomerism in Ethereal Solvents
- Application of Fluorescent Triazoles to Analytical Chemistry. III. : Fluorescence Characteristics of 2-Phenylbenzotriazolyl-5-amine Derivatives as Fluorescent Probes
- Appication of Fluorecent Triazoles to Analytical Chemistry. II. : Fluorescent Derivatization of Carboxylic Acids
- Application of Fluorescent Triazoles to Analytical Chemistry. I. Determination of Aromatic Primary Amine with 2,4,6-Triaminopyrimidine as a Reagent
- Ion Pair Extraction of Trimethoprim with Sulfonphthalein Dyes
- A New Fluorometric Method for Latamoxef in Biological Materials Using 2,6-Diamino-3-nitrosopyridine
- Equilibrium Studies on 2-(5-Methylthien-3-yl)-2,5-dihydro-3H-pyrazolo[4,3-c]quinolin-3-one (S-135) in n-Octanol
- ユウロピウム錯体修飾タンパクを試薬とするイムノアッセイ
- Fluorometric Determination of an Inverse Agonist to Benzodiazepine Receptors S-135 in Monkey Plasma by High Performance Liquid Chromatography
- Protein Binding of Quinolonecarboxylic Acids. II. : Spectral Changes on the Interaction of Cinoxacin, Nalidixic Acid and Pipemidic Acid with Human and Rat Albumins
- Protein Binding of Quinolonecarboxylic Acids. I. Cinoxacin, Nalidixic Acid and Pipemidic Acid
- Gas Chromatographic Method for the Dethrmination of Fluoride Ion in Biological Samples. II. : Stability of Fluorine-Containing Drugs and Compounds in Human Plasma
- Gas Chromatographic Method for the Determination of Fluoride Ion in Biological Samples. I. : Fluoride Level in Monkey
- Analytical Studies on 1-(2-o-Chlorobenzoyl-4-chlorophenyl)-3-dimethylcarbamoyl-5-glycylaminomethyl-1H-1,2,4-triazole Hydrochloride Dihydrate. III. High-Performance Liquid Chromatographic Method Applicable to Animal Feed(Analytical,Chemical)
- Analytical Studies on 1-(2-o-Chlorobenzoyl-4-chlorophenyl)-5-glycylaminomethyl-3-dimethylaminocarbonyl-1H-1,2,4-triazole Hydrochloride Dihydrate. II. : A Fluorometric Method Applicable to Animal Feed
- Analytical Studies on Isoxazoles. VI. Colorimetric Determination of Some Isoxazole Herbicides with p-Dimethylaminocinnamaldehyde
- Analytical Studies on Isoxazoles. V. Colorimetric Determination of Isouron and Its Isomer with p-Dimethylaminocinnamaldehyde
- Colorimetric Determination of 1-(2-o-Chlorobenzoyl-4-chlorophenyl)-5-glycylaminomethyl-3-dimethylaminocarbonyl-1H-1,2,4-triazole Hydrochloride Dihydrate with 3,5-Dibromosalicylaldehyde
- Colorimetric Determination of 4-Chloro-2-(o-chlorobenzoyl)-N-methyl-N^α-glycylglycinanilide with 3,5-Dibromosalicylaldehyde. II. Reaction Mechanism of Coloration
- Analytical Studies on Isoxazoles. IV. : Fluorometric Determination of Isouron
- ガスクロマトグラフィーによるヒト血中および尿中のベノキサプロフェングルクロン酸抱合体の定量法
- 3,5-ジブロムサリチルアルデヒドを用いる4-クロロ-2-(o-クロロベンゾイル)-N-メチル-N^α-グリシルグリシンアニリドの比色定量法
- イソキサゾール類に関する分析化学的研究(第3報)イソウロンの比色定量
- Equilibrium Studies of 5-Substituted 4-Hydroxy-2-methylpyrimidines. IV. Lactim-Lactam Tautomerism in Methanol, n-Butanol and n-Hexane
- Equilibrium Studies of 5-Substituted 4-Hydroxy-2-methylpyrimidines. III. Photometric Titration in n-Butanol
- Acid-Base Equilibria of Aniline Derivatives in n-Butanol
- Equilibrium Studies of 5-Substituted 4-Hydroxy-2-methylpyrimidines. II. Photometric Titration in Methanol
- Equilibrium Studies of 5-Substituted 4-Hydroxy-2-methylpyrimidines. I. The Ionization Constants in Aqueous Solution
- Hydrolysis of Electrophilic Olefins. II. Kinetic Studies on the Hydrolysis of m- or p-Substituted α-Benzoylcinnamonitriles
- Hydrolysis of Electrophilic Olefins. I. Kinetic Studies on the Hydrolysis of p-Dimethylaminobenzylidene Derivatives of Active Methylene Compounds
- Analytical Studies on Isoxazoles. II. A New Fluorimetric Determination of 5-Phenyl-3-isoxazolecarboxylic Acid and Its Application to the Determination of Perisoxal in Plasma
- Analytical Studies on Isoxazoles. I. A New Colorimetric Determination of 5-Substituted 3-Isoxazolecarboxylic Acids and Their Derivatives
- The Behavior of 4-Amino-5-carboxy-2-methyl-pyrimidine in Glacial Acetic Acid and in Mixed Solvent of Isopropanol and Ethyleneglycol.
- Relationship between pKa (H_2O) of 5-Substituted-4-amino-2-methylpyrimidines and Half Neutralization Potential and the Behavior of the Compounds in Nonaqueous Solvents
- The Behavior of 4-Amino-5-carboxy-2-methylpyrimidine in Aqueous Solution