Studies on Pyrimidine Derivatives. XIX. Synthesis of Isoxazolo [5,4-d] pyrimidines
スポンサーリンク
概要
- 論文の詳細を見る
5-Amino-3-phenylisoxazole-4-carbaldehyde (III) was synthesized by the Vilsmeier reaction of 5-amino-3-phenylisoxazole (I) via N, N-dimethyl-N'-(4-formyl-3-phenylisoxazol-5-yl) formamidine (II). Reaction of III with formamidine and ethyl imidates afforded 3-phenylisoxazolo [5,4-d] pyrimidine (IVa) and its 6-substituted derivatives (IVb-e), respectively. Condensation of the oxime (V) of III with ethyl orthoformate gave 3-phenylisoxazolo [5,4-d] pyrimidine 5-oxide, which was readily deoxygenated with PCl_3 to give IVa. Treatment of IVa with Grignard reagents gave 4-substituted 4,5-dihydro derivatives (VIIa, b) which were aromatized with K_3Fe (CN)_6 to yield 4-substituted isoxazolo [5,4-d] pyrimidines (VIIIa, b).
- 社団法人日本薬学会の論文
- 1980-06-25
著者
-
宮崎 浩
日本化薬(株)経営企画室
-
山中 宏
Pharmaceutical Institute, Tohoku University
-
塩沢 明
日本化薬
-
宮崎 浩
Research Laboratories of Pharmaceuticals Group, Nippon Kayaku Co., Ltd.,
関連論文
- ガスクロマトグラフィー-マススペクトロメトリー(GC/MS)によるプロスタノイド分析のための Diethylhydrogensilyl-Cyclic Diethylsilylene (DEHS-DES) 誘導体 (第2報) : GC 及び GC/MS におけるトロンボキサンB_2 Methyl Ester-Methyloxime-DEHS-DES 誘導体の挙動
- 抗がん剤の実験的評価における問題点
- 抗生物質の未来像を語る
- Condensed Heteroaromatic Ring Systems. XVI. : Synthesis of Pyrrolo[2,3-d]pyrimidine Derivatives
- Studies on Pyrimidine Derivatives. XLI. : Palladium-Catalyzed Cross-Coupling Reaction of Halopyrimidines with Aryl- and Vinyltributylstannanes
- Condensed Heteroaromatic Ring Systems. VII : Synthesis of Thienopyridines, Thienopyrimidines, and Furopyridines from o-Substituted N-Heteroarycetylenes
- Studies on Pyrimidine Derivatives. XXX. The Palladium-Catalyzed Cross-Coupling Reaction of Iodopyrimidines with Terminal Olefinic Compounds
- Studies on Quinoline and Isoquinoline Derivatives. II. Coupling Reaction of Haloquinolines and Haloisoquinolines with Monosubstituted Acetylenes in the Presence of Palladium Complex
- Studies on Pyrimidine Derivatives. X. Coupling Reaction of 5-Halopyrimidines with Olefinic Compounds in the Presence of Palladium Acetate and Triphenylphosphine
- Studies on Pyrimidine Derivatives. IX. Coupling Reaction of Monosubstituted Acetylenes with Iodopyrimidines
- Studies on Pyrimidine Derivatives. VII. Nickel-Phosphine Complex-Catalyzed Grignard Coupling of Chloropyrimidines
- Antivertigo Agents. IV. Synthesis and Antivertigo Activity of 6-[ω-(4-Aryl-1-piperazinyl) alkyl]-5,6,7,8-tetrahydro-1,6-naphthyridines
- Studies on Pyrimidine Derivatives. XXXIII. Synthesis of Alkyl Pyrimidinyl Ketones by Means of Nitrosation of Alkylpyrimidines
- Studies on Pyrimidine Derivatives. XXVII. Synthesis of 2- and 4-Pyrimidinyl Ketones by Means of the Hydration of Alkynylpyrimidines
- Studies on Pyrimidine Derivatives. XXVI. Synthesis of Derivatives containing a 1,3-Dicarbonyl Side Chain
- 新しいドラッグデザインの方向を探る
- Studies on Pyrimidine Derivatives. XXV. Reaction of Pyrimidinyl Aldehydes and Ketones with Witting Reagents
- Studies on Pyrimidine Derivatives. XX. Synthetic Utility of Hydroxymethylpyrimidines and Related Compounds
- Fusaric Acid(5-Butylpyridine-2-carboxylic Acid) と類似の構造を持つアゾールカルボン酸の代謝
- Fusaric Acid(5-Butylpyridine-2-carboxylic Acid) アザアナローグの代謝
- Isoxazole Derivatives as Centrally Acting Muscle Relaxants. II. : Synthesis and Structure-Activity Relationship of 3-Amino-N-(3-phenyl-5-isoxazolyl)propanamides
- Isoxazole Derivatives as Centrally Acting Muscle Relaxants. I. : Synthesis and Activity of 5-(3-Aminopropyl)amino-3-phenylisoxazole Derivatives
- Antivertigo Agents. V. Quantitative Structure-Activity Relationships of 6-[2-(4-Aryl-1-piperazinyl) ethyl]-5,6,7,8-tetrahydro-1,6-naphthyridines
- Antivertigo Agents. III. Synthesis of 5,6,7,8-Tetrahydro-1,6-naphthyridine Methyl Homologs
- Antivertigo Agents. II. Structure-Activity Relationships of 6-Substituted 5,6,7,8-Tetrahydro-1,6-naphthyridines
- Antivertigo Agents. I. Structure-Activity Relationships of 2-(2-Aminoethyl) pyridines
- Syntheses of Heteroaromatic Carboxylic Acids Closely Related to Fusaric Acid
- Studies on Pyrimidine Derivatives. XIX. Synthesis of Isoxazolo [5,4-d] pyrimidines
- Thiamine disulfideの臓器分布並びに代謝に関する研究
- Molecular Orbital Study of the Reactivity of Active Alkyl Groups of Pyridine and Pyrimidine Derivatives
- Studies on Ketene and Its Derivatives. XLVII. Reaction of 2-Aminopyridine with Diketene
- Studies on Ketene and Its Derivatives. XLVI. Mass Spectrometric Studies of 3-Acetyl-4-hydroxy-6-methyl-1-pyridyl-2-pyridones and N-Pyridyl-2,6-dimethyl-4-pyrone-3-carboxamides
- Studies on the Metabolism of Unsaturated Fatty Acids. VII. Separation and General Properties of Reduced Nicotinamide Adenine Dinucleotide Phosphate-dependent trans-2-Enoyl-Coenzyme A Reductase from Escherichia coli K-12
- Studies on the Metabolism of Unsaturated Fatty Acids. VI. Stereochemical Studies of the Reaction catalyzed by cis-2-Enoyl-Coenzyme A Reductase of Escherichia coli
- Studies on the Metabolism of Unsaturated Fatty Acids. V. Isomerization of Thiol Esters of cis-2-Alkenoic Acids during Their Preparation and Alkaline Hydrolysis
- Studies on Pyrimidine Derivatives. XXIV. Synthesis of 3-Substituted 1,2,4-Triazines by Nucleophilic Substitution
- Studies on the Metabolism of Unsaturated Fatty Acids. IV. N-Ethylmaleimide Reducing Activity in Escherichia coli K-12
- Studies on the Metabolism of Unsaturated Fatty Acids. III. Structural Determination of cis- and trans-Isomers of 3- or 2-Alkenoic Acids by Nuclear Magnetic Resonance Spectroscopy using a Chemical Shift Reagent
- Studies on Pyrimidine Derivatives. XIV. On the Structural Determination of Pyrimidine N-Oxides
- Studies on the Metabolism of Unsaturated Fatty Acids. II. Separation and General Properties of Reduced Nicotinamide Adenine Dinucleotide Phosphate dependent cis-2-Enoyl-Coenzyme A Reductase from Escherichia coli K-12
- Studies on Pyrimidine Derivatives. XII. Reaction of 4,6-Disubstituted Pyrimidine N-Oxides with Dimethyl Acetylenedicarboxylate
- Studies on the Metabolism of Unsaturated Fatty Acids. I. Synthesis and Identification of 6-Hydroxydodec-3-cis-enoic Acid, the Final Metabolite of Ricinoleic Acid by Escherichia coli K-12
- 日米合同薬学大会を振り返って
- 高速液体クロマトグラフィーによる生体試料中エトポシドの定量 : 自動前処理法の開発(医薬品の分析)
- 医薬品開発と薬価を考える
- 四重極GC-MS装置
- Palladium-Catalyzed Condensatino of Aryl Halides with Phenylsulfonylsulfonylacetonitrile and Diethyl Cyanomethyl phosphonate
- Cross-Coupling of N-Heteroaryl Halides with Active Methylene Compounds in the Presence of Tetrakis(triphenylphosphine)palladium
- 321. ダイアジノンの稲体中に於ける動態について
- MNDO (Modified Neglect of Diatomic Overlap) Study of the Nucleophilic Substitution Reactions of Chloropyrimidines
- Mass Fragmentographic Determination of 1-Piperidino-2,4'-dimethylpropiophenone (Mydocalm) by Use of 1 : 1 Mixture Technique
- Studies on Pyrimidine Derivatives. XXI. Nucleophilic Substitution of 4-Chloropyrimidines and Related Compounds with Carbanions
- Studies on Pyrimidine Derivatives. XVIII. Reaction of Active Methyl Groups on Pyrimidine N-Oxides
- Studies on Quinoline and Isoquinoline Derivatives. III. Reaction of Quinoline 1-Oxide with 2-Substituted Ethyl Acetimidates
- Studies on Pyrimidine Derivatives. VIII. Ring-Cleavage Reaction of 4,6-Dimethylpyrimidine 1-Oxide
- マススペクトロメトリー最近の進歩
- Studies on Ketene and Its Derivatives. LX. Reaction of Diketene with Quinoline 1-Oxide (Supplement)
- Studies on as-Triazine Derivatives. XVI. Reaction of 1,2,4-Triazinecarbonitriles with Carbanions
- Studies on as-Triazine Derivatives. XII. : Synthesis of Alkenyl-1,2,4-triazine Derivatives
- Studies on as-Triazine Derivatives. IX. Synthesis of 5-Substituted 1, 2, 4-Triazine Derivatives through an Addition Reaction and Subsequent Oxidation(Organic,Chemical)
- Studies on Quinoline and Isoquinoline Derivatives. VIII. Hydration and Hydrogenation of Ethynyl Substituents attached to the Pyridine Moiety of Quinoline and Isoquinoline Rings
- Hydration and Hydrogenation of Acetylenic Side-Chains at the 4- or 5-Position of Isoxazoles
- Studies on Pyrimidine Derivatives. XXIII. Synthesis of Acylmethylpyrimidines and Related Compounds via Imidoyl-substituted Oxosulfonium Ylides
- プロスタノイドの微量分析法
- Studies on Quinoline and Isoquinoline Derivatives. IV. Reaction of Quinoline and Isoquinoline N-Oxides with 3-Amino-crotononitrile and Related Compounds
- Studies on Quinoline and Isoquinoline Derivatives. I. Condensation of Quinoline and Isoquinoline N-Oxides with Isoxazoles
- Synthesis of Ethoxyethynylarenes by the Palladium-Catalyzed Reaction of Aryl Iodides with Ethoxy(trialkylstannyl)acetylenes
- 1,3-Dipolar Cycloaddition Reaction of Substituted Trimethylstannylacetylenes with Nitrile Oxides
- Condensed Heteroaromatic Ring Systems. XXI.Synthesis of Pyrrolo[2,3-d]pyrimidines and pyrrolo[3,2-d]pyrimidines
- Condensed Heteroaromatic Ring Systems. XX. Palladium-Catalyzed Carbonylative Coupling of Iodobenzenes with (Z)-1-Ethoxy-2-(tributylstannyl)ethene
- Palladium-Catalyzed Coupling Reaction of 3-Iodoindoles and 3-Iodobenzo[b]thiophene with Terminal Acetylenes
- Site-Selectivity in the Reaction of 3-Substituted Pyridine 1-Oxides with Phosphoryl Chloride
- Condensed Heteroaromatic Ring Systems. XV. : Synthesis of Pyranopyridinones from Halopyridinecarbonitriles
- Condensed Heteroaromatic Ring Systems. XIII. : One-Step Synthesis of 2-Substituted 1-Methylsulfonylindoles from N-(2-Halophenyl)methanesulfonamides
- Studies on Pyrimidine Derivatives. XL. : Ring Transformation of 4-Alkoxypyrimidine 1-Oxides by Reaction with Diketene
- Condensed Heteroaromatic Ring Systems. XII. Synthesis of Indole Derivatives from Ethyl 2-Bromocarbanilates(Organic,Chemical)
- Studies on Ketene and its Derivatives. VI. Reaction of Diketene with Aminopyridines and their N-Oxides
- Studies on Ketene and Its Derivatives. XXVIII. Reaction of β-Aminocrotonamide with Ketene and Diketene
- Reductive Amination of Ethynylpyridines with Sodium Cyanoborohydride
- Condensed Heteroaromatic Ring Systems. IX. : Total Synthesis of Aaptamine
- Condensed Heteroaromatic Ring Systems. V. : Formal Synthesis of Matrine and Related Compounds Using Palladium-Catalyzed Carbon-Carbon Bond Formations as Key Reactions
- Palladium-Catalyzed Reactions of Terminal Acetylenes and Olefins with Halo-1,3-azoles(Organic,Chemical)
- Studies on Pyrimidine Derivatives. XV. Homolytic Acylation and Amidation of Simply Substituted Pyrimidines
- Studies on the Synthesis of Indole Related Compounds. II. Diels-Alder Reaction of Phenacylidene Indolinone
- Studies on Quinoline and Isoquinoline Derivatives. IX. Synthesis of Pyrrolo [1,2-b] isoquinolines from 3-Bromoisoquinoline Derivatives
- Cross-coupling Reactions of Haloisoxazoles with Olefins and Acetylenes
- Studies on Pyrimidine Derivatives. VI. On the Reactivity of the 2-Methyl Group of 1,2,4-Trimethyl-6-oxo-1,6-dihydropyrimidine
- Studies on Pyrimidine Derivatives. II. Reaction of Some Dimethyl and Trimethyl-heteroaromatics with Ethyl Nitrite
- N-Oxidation of 4-Chloropyrimidine Derivatives
- Studies on Ketene and Its Derivatives. XXXII. Reactions of α, β-Unsaturated Acid Anhydride with β-Aminocrotonamide and Related Compounds
- Site-Selectivity in the Cyanation of 3-Substituted Pyridine 1-Oxides with Trimethylsilanecarbonitrile
- Studies on Ketene and Its Derivatives. XII. The Structure of the Self-Condensation Product of Acetoacetamide.
- Studies on Pyrimidine Derivatives. XXXIV. Substituent Effect on the Reaction of 4-Substituted 2,6-Dimethylpyrimidine 1-Oxides with Acetic Anhydride
- Studies on Pyrimidine Derivatives. XXXII. Reaction of 4-Substituted 2,6-Dimethylpyrimidine 1-Oxides with Phosphoryl Chloride
- Studies on Pyrimidine Derivatives. XXXVI. Reaction of 6-Substituted 2,4-Dimethylpyrimidines with Benzaldehyde in the Presence of Zinc Chloride
- Condensed Heteroaromatic Ring Systems. III. Synthesis of Naphthyridine Derivatives by Cyclization of Ethynylpyridinecarboxamides
- Condensed Heteroaromatic Ring Systems. VIII. : Synthesis of 3-Substituted Isocoumarins from o-Halobenzoic Acid Derivatives
- Condensed Heteroaromatic Ring Systems. VI. : Synthesis of Indoles and Pyroolopyridines from o-Nitroarylacetylenes
- Condensed Heteroaromatic Ring Systems. IV. Synthesis of Naphthyridine Derivatives by Cyclization of Aminopyridineacrylic Esters
- Studies on Pyrimidine Derivatives. XXXVIII. Cross-Coupling Reaction of N-Heteroaryl Iodides with Ethoxycarbonylmethylzinc Bromide in the Presence of Palladium Catalyst