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

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概要

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• The synthesis of alkyl N-cyano cyanoacetimidates (II) and the action of hydrogen halides on II have been examined. The reaction of alkyl cyanoacetimidates (I) with cyanamide in the presence of a dispersing agent gave II in good yields. The cyclization of II with hydrogen chloride gave a mixture of 4-alkoxy-6-amino-2-chloropyrimidines (IV) and 4-alkoxy-2-amino-6-chloropyrimidines (V), but the addition of a Lewis acid led the cyclization in one specific direction exclusively giving IV. Hydrogen bromide and iodide effected cyclization reversely to give 2-amino-6-bromo-4-hydroxy (alkoxy) pyrimidines (IX, X) and 2-amino-4-hydroxy-6-iodopyrimidine (XII) as main products, respectively.

• 公益社団法人日本薬学会の論文
• 1976-03-25

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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