“Masked Ketone” を利用する新しいピリミジン合成法
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概要
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A new synthetic method of pyrimidines by the reaction of α, α-diamino compounds such as guanidine, amidine, thiourea and urea with <I>O</I>-heterocyclic compounds having oxyvinyl-carbonyl or oxyvinylnitrile moiety in the hetero-aromatic ring is described. The <I>O</I>-heterocyclic compounds-considered as “masked ketone” -which play a role as “three-carbon fragment” for the formation of pyrimidines in the above reaction are classified into the following three groupes : (1) benzofurans substituted at position 3 by electron-attracting group, (2) benzo-γ-pyrones, and benzo-α-pyrones, and (3) γ-pyrones. Thus from these oxygen heterocycles were obtained the new derivatives of 5-(2-hydroxyphenyl) pyrimidine, 4- (2-hydroxyphenyl) pyrimidine, and 4-acetonylpyri midine, respectively. The influences of the three factors on the formation of pyrimidines are discussed : (1) structure of the starting oxygen heterocycle, (2) reactivity of the α, α-diamino compounds as nucleophilic reagent, and (3) reaction conditions used.
- 社団法人 有機合成化学協会の論文