Studies on Pyrimidine Derivatives. II. Synthesis of Thiazolo [5,4-d] pyrimidines and Related Compounds. (2).

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概要

• 論文の詳細を見る

• 1) The reaction of 2-chloro-4-thiocyano-5-nitropyrimidine (I) with aq. NH_4OH, EtNH_2,thiourea, or sodium phenoxide gave 2,4-disubstituted derivatives. The reaction of (I) with ethanolic NH_4OH and aniline respectively gave 2-amino-4-thiocyano-5-nitropyrimidine (V) and 2-anilino-4-thiocyano-5-nitropyrimidine (IX), and the reaction of (V) or (IX) with sodium alkoxide gave 2-amino-4-mercapto-(XIV) and 2-anilino-4-mercapto-5-nitropyrimidine (XV). 2) The reduction of (V) and (IX) afforded the corresponding 2-aminothiazolo [5,4-d]-pyrimidines, and the reduction of (XIV) and (XV) gave 2,5-diamino-4-mercapto-(XVII) and 2-anilino-4-mercapto-5-aminopyrimidine (XVIII), respectively. The cyclization of (XVII) and (XVIII) with formic acid, acetic anhydride, benzoyl chloride, or potassium methylxanthate, gave the corresponding 2-substituted (H, CH_3,C_6H_5,SH) thiazolo [5,4-d]-pyrimidines. 3) In the presence of alkali, 2-aminothiazolo [5,4-d] pyrimidines were hydrolysed to the 4-mercapto-5-aminopyrimidine derivatives via the (4-mercapto-5-pyrimidyl) ureas.

• 公益社団法人日本薬学会の論文
• 1958-08-15

著者

• 井上 昭二

  Pharmaceutical Faculty Nagoya City University

• 内藤 多喜夫

  Faculty of Pharmacy, Meijo University

• 内藤 多喜夫

  Pharmaceutical Faculty, Nagoya City University

• 内藤 多喜夫

  Faculty Of Pharmacy Meijo University

関連論文

• Studies on Pyrimidine Derivatives. X
• Studies on Pyrimidine Derivatives. IX. Synthesis of Some Alkylamino- and Alkylthio-, Thiazolo (5,4-d) pyrimidines. (2)
• Studies on Pyrimidine Derivatives. VIII. Synthesis of Some Alkylamino- and Alkylthio-, Thiazolo (5,4-d) pyrimidines. (1)
• Studies on Pyrimidine Derivatives. VII. Synthesis of Thiazolo [5,4-d] pyrimidines and Related Compounds. (7)
• Studies on Pyrimidine Derivatives. VI. Synthesis of Thiazolo [5,4-d] pyrimidines and Related Compounds. (6).
• Studies on Pyrimidine Derivatives. V. Synthesis of Thiazolo [5,4-d] pyrimidines and Related Compounds. (5).
• Studies on Pyrimidine Derivatives. IV. Synthesis of Thiazolo [5,4-d] pyrimidines and Related Compounds. (4).
• Studies on Pyrimidine Derivatives. III. Synthesis of Thiazolo [5,4-d] pyrimidines and Related Compounds. (3).
• Studies on Pyrimidine Derivatives. II. Synthesis of Thiazolo [5,4-d] pyrimidines and Related Compounds. (2).
• Studies on Pyrimidine Derivatives. I. Synthesis of Thiazolo [5,4-d]-pyrimidines and Related Compounds. (1).

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