Studies on Pyrimidine Derivatives and Related Compounds. XLIV. Syntheses of Thiazolo [3,2-a] pyrimidine Derivatives

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概要

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• Ethyl 2-thio-1,2,3,4-tetrahydropyrimidine-5-carboxylate (VIII) and 2-thio-1,2,3,4-tetrahydropyrimidine-5-carbonitrile (XXIII) were used for various kinds of condensation reactions. From the reaction with ethylene dibromide, VIII gave biscompound IX, and with phenacyl-bromide and p-chlorophenacylbromide thiazolo [3,2-a] pyrimidine derivatives were obtained. In this reaction, 5H-thiazolo [3,2-a] pyrimidine derivative (XIII, XVII, XXV) and the 7H-isomer (XIV, XVIII, XXVI) were obtained separately. The structures of these isomers were assigned from NMR and UV spectra. In this thiazolo [3,2-a] pyrimidine syntheses, 3-hydroxy compounds (XII, XVI, XXIV) were considered to be the key intermediates.

• 公益社団法人日本薬学会の論文
• 1967-06-25

著者

• 高見沢 映

  Shionogi Research Laboratory, Shionogi & Co., Ltd.

• 平井 健太郎

  Shionogi Research Laboratory, Shionogi & Co., Ltd.

• 松本 至博

  Shionogi Research Laboratory, Shionogi & Co., Ltd.

• 石破 暉之

  Shionogi Research Laboratory, Shionogi & Co., Ltd.

• 松本 至博

  Shionogi Research Laboratory Shionogi & Co. Ltd.

• 高見沢 映

  Shionogi Research Laboratory Shionogi & Co. Ltd.

• 石破 暉之

  Shionogi Research Laboratory Shionogi & Co. Ltd.

関連論文

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• Studies on Pyrimidine Derivatives and Related Compounds. XLVII. Reaction of Thiamine with Dialkyl Acylphos-phonates or Methyl Phenylacyl-phosphinates : Takamizawa Reaction 6
• Studies on Pyrimidine Derivatives and Related Compounds. XLVI. The Reactions of Diethyl Acetylphosphonate with Thiamine : Takamizawa Reaction (5).
• Studies on the Pyrimidine Derivatives and Related Compounds. XL. Reaction of 3-Benzyl-4-methyl-5-(2-hydroxyethyl)thiazolium Salts with Diethyl Benzoylphosphonate
• Studies on the Pyrimidine Derivatives and Related Compounds. XXXIX. On the Oxidation Products of 2-Pheny1-4-(2-methyl-4-amino-5-pyrimidyl)methyl-5-methyl-6-(2-benzoyloxy or hydroxy)-ethyl-4H-1,4-thiazin-3(2H)-one
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• Studies on the Pyrimidine Derivatives. XXVII. A New Method for Synthesis of Diethyl Ethoxycarbonylphosphite from Tris (ethoxythiocarbonyl) Phosphorotrithioite, and on the Reactions of these Organo-phosphorus Compounds with Thiamine Sodium Salt.
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• On the Reaction of Dialkyl Acylphosphonate with 2-Methyl-1,3,4-thiadiazolium Salts
• On the Reaction of Dialkyl Acylphosphonate with 2-Methylthiazolium Salts
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• Studies on Pyrimidine Derivatives and Related Compounds. LXIX. Sythesis of Thiamine Free Base
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• Studies on Pyrimidine Derivatives and Related Compounds. LXVII. Reaction of Thiadiazolium Derivatives with Dialkyl Acylphosphonates
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• Syntheses of 2-Disubstituted-amino-4-arylthiazol-5-ylalkanoic Acids
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