Studies on Ketene and Its Derivatives. LXXXV. Reactions of 4-Bromo-3-hydroxybutanoate and Its Acyl Derivatives
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概要
- 論文の詳細を見る
Acylation of ethyl 4-bromo-3-hydroxybutanoate (I) with acetic anhydride, benzoyl chloride, diketene, and phenyl isocyanate gave rise to ethyl 3-acetoxy-4-bromobutanoate (IIa), ethyl 3-benzoyloxy-4-bromobutanoate (IIb), ethyl 3-acetoacetoxy-4-bromobutanoate (IIc), and ethyl 4-bromo-3-(N-phenylcarbamoyloxy) butanoate (IId), respectively. Reaction of IIa with sodium ethoxide in abs. ethanol gave ethyl 4-hydroxycrotonate (III) and ethyl 4-bromocrotonate (IV). The similar reaction of IIb afforded IV and 4-benzoyloxycrotonate (Vb). Similarly, IIc was converted to III, 4-acetoacetoxycrotonate (Vc), and 3-acetyl-4-ethoxycarbonylmethyltetrahydrofuran-2-one (VI). On the other hand, reaction of IId under the same condition did not give the acyl migrated product such as ethyl 4-N-phenylcarbamoyloxycrotonate (Vd) but afforded ethyl 4-anilinocrotonate (VIII).
- 社団法人日本薬学会の論文
- 1977-10-25
著者
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加藤 鉄三
Pharmaceutical Institute, Tohoku University
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加藤 鉄三
Pharmaceutical Institute Tohoku University
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木村 仁
Pharmaceutical Institute, Tohoku University
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木村 仁
Pharmaceutical Institute Tohoku University
関連論文
- Diketeneより誘導された化合物, ならびに関連化合物の抗腫瘍性スクリーニング
- General Pharmacological Actions of N-Acetoacetyl-3-hydroxytyrosine
- Studies on Ketene and Its Derivatives. XCV. Reaction of Diketene with Acyl Azides
- Synthesis of dl-Dehydroiridodiol
- Studies on Ketene and Its Derivatives. CI. Reaction of Diketene with 4-Amino-methylpyridine 1-Oxides
- Synthesis of Dihydrojasmone and cis-Jasmone
- Reaction of Ethyl 4-Halo-3-oxobutanoate with Diethyl Malonate, Methyl Cyanoacetate, and Malononitrile
- Studies on Ketene and Its Derivatives. LXXXV. Reactions of 4-Bromo-3-hydroxybutanoate and Its Acyl Derivatives
- Synthesis of Methylpyridine Derivatives. XXX. Reaction of Active Methylene Compounds with 6-Methyl-2-phenyl-4H-1,3-oxazin-4-one and 2-Ethoxy-2,6-dimethyl-2H-1,3-oxazin-4 (3H)-one to give 3-Acetylpyridone Derivatives
- Studies on Ketene and Its Derivatives. LVII. Reaction of Diketene with β-Diketones
- Studies on Ketene and Its Derivatives. LIV. Reaction of Diketene with Ketene Acetals
- Studies on Ketene and Its Derivatives. XVIII. Reaction of Diketene with Acridine.
- Studies on Ketene and Its Derivatives. XVII. Reaction of Diketene with Imidates.
- Studies on Ketene and Its Derivatives. XI. Reaction of Diketene with Phenanthridine
- Studies on Ketene and its Derivatives. X. Reaction of Diketene with Schiff Base
- Reaction of Ethyl 4-Bromoacetoacetate with Carbon Disulfide and Active Methylene Compounds
- Neighboring Group Participation of the N-Oxide Group in the Reaction of Methyl 1-Oxido-2-pyridyl Ketone Oxime with Tosyl Chloride
- Reaction of 4-Haloacetoacetate with Phenols in the Presence of Aluminum Chloride
- Studies on Ketene and Its Derivatives. CVII. Photoreaction of Diketene with 6-Methyluracil
- Studies on Ketene and Its Derivatives. CVI. Photoreaction of Diketene with N-Phenylmaleimide and Dimethyl-N-phenylmaleimide
- Studies on Ketene and Its Derivatives. CII. Reaction of Diketene with Cyanamide Derivatives
- Studies on Ketene and Its Derivatives. XCVII. Photoreactions of Diketene with Maleic Anhydride and Dimethylmaleic Anhydride
- Studies on Ketene and Its Derivatives. XCVI. Synthesis of Pyrido [2,1-b] benzoazoles
- Reaction of Ethyl Acetoacetate with Isoquinolinium and Pyridinium Ylides
- Synthesis of Methylpyridine Derivatives. XXXII. Reaction of Pyridine, Quinoline, and Isoquinoline with 4-Bromoacetoacetic Acid Derivatives and Synthesis of Indolizine Derivatives
- Reaction of Diazomethane with 2-Acetyl-5,5-diphenyl-2,4-pentadienoic Acid and Related Compounds
- Studies on Ketene and Its Derivatives. LXXXIV. Reaction of Diketene with Tetrazole Derivatives
- Studies on Ketene and Its Derivatives. LXXVII. Reaction of Diketene with Pyridineformimidates and Related Compounds to give 1,3-Oxazin-4-one Derivatives
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- Ring Transformation of 5-Oxo-4-oxaspiro [2.3] hexanes
- Studies on Ketene and Its Derivatives. XCIV. Reaction of Diketene with Diazoacetone and 2-Diazoesters
- Chemical Reactions of Bikaverin
- Studies on Ketene and Its Derivatives. LIII. Reaction of Diketene with Diazoacetophenone and Ethyl Diazoacetate
- Studies on Ketene and Its Derivatives. XLVIII. Reaction of Diketene with Hydroxylamine
- 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 Organometallic Compounds. I. Insertion Reaction of Diketene into N-Si Bond of Silylated Amides
- Studies on Ketene and Its Derivatives. LX. Reaction of Diketene with Quinoline 1-Oxide (Supplement)
- Synthesis of Methylpyridine Derivatives. XXVII. Synthesis of 1,3-Disubstituted-4-oxo-quinolizine and 2,4-Disubstituted-1-oxo-benzo [c] quinolizine Derivatives
- Studies on Ketene and Its Derivatives. XLIX. Reaction of Diketene with β-Ketoesters to give Ethyl Orsellinate, Divarate, Olivetol Carboxylate, and Sphaeropherol Carboxylate
- Synthesis of N-Acylacetoacetamide using 2,2,6-Trimethyl-1,3-dioxin-4-one
- Studies on Ketene and Its Derivatives. CV. Photoreaction of Diketene with sec-Alcohols
- Synthesis of Methylpyridine Derivatives. XXXIV. Condensation of Acetoacetamide with Ketones to form Pyridone Derivatives
- Studies on Ketene and Its Derivatives. XCII. Reaction of Diketene with Benzaldehyde, Cinnamaldehyde, and β-Phenylcinnamaldehyde
- Studies on Ketene and Its Derivatives. LXXXVII. Photoreaction of Diketene with 3-Acetoxy-5,5-dimethyl-2-cyclohexenone
- Studies on Ketene and Its Derivatives. LXVII. Photoreaction of Benzophenone and Benzaldehyde with Diketene
- Structure of the Product from the Reaction of Acetonedicarboxylic Acid with Acetic Anhydride
- 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
- Reaction of Methyl 1-Oxido-2-pyridyl Ketone Oxime with Acetic Anhydride : Formation of a 3-Methylisoxazolo[4,5-b]pyridine Derivative(Organic,Chemical)
- Reaction of γ-Bromoacetoacetyl Compounds with Benzamide Oxime Derivatives : Synthesis of 4H-1,2,4-Oxadiazine Derivatives
- Cyclization of O-Acetoacetylbenzamide Oxime Derivatives
- Reaction of N-Hydroxyacetoacetanilide with Carbonyl Reagents
- Organic Sulfites containing a 1,2-Oxazine Ring
- Reaction of γ-Bromoacetoacetyl Bromide with N-Phenylhydroxylamine Derivatives : Synthesis of 1,2-Oxazine Derivatives
- Studies on Ketene and Its Derivatives. LXXIX. Reaction of Diketene with Benzimidazole and 2-Methylbenzimidazole Derivatives
- Studies on Ketene and Its Derivatives. LXXXII. Reaction of Diketene with N-Phenylhydroxylamine Derivatives
- Studies on Ketene and Its Derivatives. LXXXI. Reaction of β-Aminocrotonamide with α, β-Unsaturated Ketones
- Studies on Ketene and Its Derivatives. LXXVI. Reactions of Acetoacetamide and β-Aminocrotonamide with β-Diketone, β-Ketoaldehyde and Related Compounds
- Studies on Ketene and Its Derivatives. LXXIV. Carroll Reaction of 1,1-Diphenyl-2-propynyl Acetoacetate
- Studies on Ketene and Its Derivatives. LXXIII. Synthesis of Pyrido [1,2-a]-pyrimidin-4-one and Pyrido [1,2-a] sym-triazin-4-one Derivatives
- Synthesis of Methylpyridine Derivative. XXXI. Reaction of Aceto-acetamide with α, β-Unsturated Ketones and Aldehydes
- Studies on Ketene and Its Derivatives. LXVIII. Reaction of Diketene with N-Imino-pyridinium, -quinolinium, and -isoquinolium Ylides
- Studies on Ketene and Its Derivatives. LXVI. Reaction of Acetoacetamide with α, β-Unsaturated Esters
- Studies on Ketene and Its Derivatives. LXII. Reaction of Ketene and Diketene with 2-Pyridyl Isocyanate and Isothiocyanate
- Synthesis of Methylpyridine Derivatives. XVI. The Reaction of Picolines and their N-Oxides with Amyl Nitrite.
- Synthesis of 1-Substituted-1,2,5,6-tetrahydro-4H-pyrrolo (3,2,1-ij) quinolin-2-one
- Studies on Ketene and Its Derivatives. XXXIX. Reaction of Diketene with Semicarbazone
- Studies on Ketene and Its Derivatives. XXXVIII. Reaction of Diketene with Phenylhydrazones to give 4-Acetyl-2-phenylpyrazolidin-3-ones
- Studies on the Synthesis of Indole Related Compounds. II. Diels-Alder Reaction of Phenacylidene Indolinone
- Synthesis of Methylpyridine Derivatives (XXI). Amination of Chloro-2,6-lutidines and Their N-Oxides via a Hetaryne Mechanism
- 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
- Studies on Ketene and Its Derivatives. XII. The Structure of the Self-Condensation Product of Acetoacetamide.
- Reactivities of 4-Chloropyridine Derivatives and Their 1-Oxides.
- Studies on Ketene and Its Derivatives. XXXI. 2-Acetonyloxazolines