Chemical and Pharmaceutical Bulletin
Online ISSN : 1347-5223
Print ISSN : 0009-2363
ISSN-L : 0009-2363
A Novel Synthesis of Pyrimidines. I. Cyclization of N-Cyano-cyanoaceto Derivatives
平山 忠允鎌田 政宏鶴見 秀昭三村 雅隆
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1976 年 24 巻 1 号 p. 26-35

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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).

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