Xanthine及び関係化合物の研究(第2報)4-Amino-5-phenylazouracilよりXanthineの一新合成法

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概要

• 論文の詳細を見る

• Xanthine was synthesized through a new process using 4-amino-5-phenylazouracil as the intermediate. The new compound, 4-amino-5-phenylazouracil, was prepared by two methods : (i) Coupling 4-aminouracil with phenyldiazonium chloride, and (ii) phenylazocyanoacetylurea, obtained by coupling cyanoacetylurea with phenyldiazonium chloride, cyclized by alkali hydroxide solution. Reduction of 4-amino-5-phenylazouracil to give 4,5-diaminouracil was carried out by either zinc with a mineral acid or a catalytic hydrogenation. Its reduction with zinc and 90% formic acid resulted in the formation of 4-amino-5-formylaminouracil. Xanthine was obtained when it was heated with formamide or hydrogenated in the presence of formamide using Raney nickel catalyst under pressure. The latter method gave a higher yield of xanthine.

• 公益社団法人日本薬学会の論文
• 1955-06-20

著者

• 関屋 実

  Shizuoka College of Pharmacy

• 石館 守三

  Pharmaceutical Institute Medical Faculty University Of Tokyo

• 原田 雄吉

  Shizuoka College of Pharmacy

• 尾崎 義郎

  Shizuoka Caffeine Co., Ltd.

• 栗田 一郎

  Shizuoka Caffeine Co., Ltd.

• 尾崎 義郎

  静岡薬科大学

• 栗田 一郎

  Shizuoka Caffeine Co. Ltd.

関連論文

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• 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
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• Preparations of N-Alkylthiomethyl and N-Amidomethyl Derivatives of Amino Acids
• Chemical Behaviors of 1,1'-Diacetyl-1,1', 4,4'-tetrahydro-4,4'-bipyridine toward Organic Hydrogen Acceptors
• A New Convenient Synthesis of Diazoalkanes from N-[(N-Nitrosoalkylamino) methyl] benzamides
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• Reductive Cleavage Reaction of N, N'-, N, O- and N, S-Linked Alkylidene Compounds by Sodium Borohydride
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• 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
• 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
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• 1,3-DIPOLAR CYCLOADDITION LEADING TO N-ALKYLPYRROLIDINES
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• Decarboxylation Reactions. I. Reaction of Enamines with Carboxylic Acids

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