A Novel Synthesis of Pyrimidines. I. Cyclization of N-Cyano-cyanoaceto Derivatives

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概要

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• The action of anhydrous hydrogen chloride and bromide on sodium cyanoacetylcyanamides (II) and N-cyano-cyanoacetamidines (IV) was shown to undergo cyclization to give exclusively corresponding 2-halogenopyrimidines (VI, XV), whereas the hydrogen iodide treatment of II caused no cyclization and that of IV gave an unexpected 6-amino-4-iodopyrimidine (XVI). The reaction of II with alcoholic hydrogen chloride afforded 2,6-dialkoxy-4-hydroxypyrimidines (VIII) via N-cyanoacetyl-O-alkylisoureas (VII). The intermediates (VII) were independently cyclized in water with heating to give 2-alkoxy-6-amino-4-hydroxypyrimidines (IX).

• 公益社団法人日本薬学会の論文
• 1976-01-25

著者

• 鎌田 政宏

  Research Institute Daiichi Seiyaku Co. Ltd.

• 平山 忠允

  Research Institute, Daiichi Seiyaku Co., Ltd.

• 三村 雅隆

  Research Institute, Daiichi Seiyaku Co., Ltd.

• 鶴見 秀昭

  Research Institute, Daiichi Seiyaku Co., Ltd.

• 三村 雅隆

  Research Institute Daiichi Seiyaku Co. Ltd.

• 鶴見 秀昭

  Research Institute Daiichi Seiyaku Co. Ltd.

関連論文

• A Novel Synthesis of Pyrimidines. II. Cyclization of Alkyl N-Cyano Cyanoacetimidates with Hydrogen Halides
• A Novel Synthesis of Pyrimidines. I. Cyclization of N-Cyano-cyanoaceto Derivatives

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